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Description: Download file or read online AP past exam paper 2014 AP Chemistry Practice Exam MCQ Multiple Choice Questions with Answers and FRQ Free Response Questions with Scoring Guidelines - Collegeboard Advanced Placement.

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AP ® Chemistry Practice Exam From the 2 014 Administration NOTE : This is a modified version of the 201 4 AP Chemistry Exam. Thi s Practic e Exa m is provided by the Colleg e Boar d fo r AP Exam preparation . Teacher s ar e permitted to download the material s an d mak e copies to use wit h thei r student s in a classroo m settin g onl y. T o maintai n th e securit y of this exam , teacher s shoul d collec t al l material s afte r thei r administratio n an d keep the m in a secure location . Exam s ma y no t be poste d on schoo l or personal websites, no r electronically redistributed for an y reason. Fu rther distributio n of thes e material s outside of the secur e Colleg e Board sit e disadvantages teacher s wh o rel y on uncirculated questions for classroo m testing . An y additional distribution is in violation of the Colleg e Board ’s copyright policies an d ma y resul t in the terminatio n of Practic e Exa m acces s fo r you r schoo l as well as the removal of access to other online services such as the A P Teache r Communit y an d Onlin e Scor e Repo rts.

Contents Exam Instructions Student Answer Sheet for the Multiple -Choice Section Section I: Multiple -Choice Questions Section II: Free -Response Questions Multiple -Choice Answer Key Free- Response Scoring Guidelines Scoring Worksheet Note: This publication shows the page numbers that appeared in the 2013−14 AP Exam Instructions book and in th e actual exam. This publication was not repaginated to begin with page 1. © 2014 The College Board. College Board, Advanced Placement Program, AP, SAT and the acorn logo are registered trademarks of the College Board. All other products and services may be trademarks of their respective owners. Permission to use copyrighted College Board materials may be requested online at: www.collegeboard.com/inquiry/cbpermit.html.

Exam Instructions The following contains instructions taken from the 2013−14 AP Exam Instructions book.

41 CHEMISTRY What Proctors Need to Bring to This Exam • . • . • . • . • . • . • . • .Exam .packets Answer .sheets AP .Student .Packs 2013-14 AP Coor\binator’s Manual . This .book .— .AP Ex am I nstructions . School .Code .and .Home-School/Self- Stu dy .C odes Extra .calculators Pencil .sharpener • . • . • . • . • . • .Extra .No . .2 .pencils .with .erasers Extra .pens .with .black .or .dark .blue .ink Extra .paper Stapler Watch Signs .for .the .door .to .the .testing .room . . . . .– . . .– . . . . . . . . “Exam .in .Progress” “Cell .phones .are .prohibited .in .the . .t es ti ng .room” Note: .this .year, .tables .of .equations .and .constants .are .provided .in .the .exam .booklets .for .both . sections .of .the .exam . Students .are .not .allowed .to .use .calculators .in .Section .I .of .the .AP .Chemistry .Exam . .However, . students .are .permitted .to .use .four-function, .scientific, .or .graphing .calculators .to .answer . questions .in .Section .II . .Before .starting .the .exam .administration, .make .sure .that .each .student .has . an .appropriate .calculator .and .that .any .student .with .a .graphing .calculator .has .a .model .from .the . approved .list .on .page .\b5 .of .the . 2013-14 AP Coor\binator’s Manual . .See .pages .\b2–\b5 .of .the . 2013-14 AP Coor\binator’s Manual .for .more .information . .If .a .student .does .not .have .an .appropriate . calculator .or .has .a .graphing .calculator .not .on .the .approved .list, .you .may .provide .one .from .your . supply . .If .the .student .does .not .want .to .use .the .calculator .you .provide, .or .does .not .want .to .use .a . calculator .at .all, .he .or .she .must .hand .copy, .date, .and .sign .the .release .statement .on .page .\b3 .of .the . 2013-14 AP Coor\binator’s Manual . During .the .administration .of .Section .II .students .may .have .no .more .than .two .calculators .on . their .desks . .Calculators .may .not .be .shared . .Calculator .memories .do .not .need .to .be .cleared . before .or .after .the .exam . .Students .with .Hewlett-Packard .\b8–50 .Series .and .Casio .FX-9860 . graphing .calculators .may .use .cards .designed .for .use .with .these .calculators . .Proctors .should .make . sure .infrared .ports .(Hewlett-Packard) .are .not .facing .each .other . .Since graphing calculators can be used to store data, including text, proctors should monitor that students are using their calculators appropriately. Attempts by students to use the calculator to remove exam questions and/or answers \brom the room may result in the cancellation o\b AP Exam scores. Students .will .be .allowed .to .use .the .table .of .equations .and .constants .on .both .sections .of .the .exam . SECTION I: Multiple Choice ! Do not begin the exam instructions below until you have completed the appropriate General Instructions \bor your group. Make .sure .you .begin .the .exam .at .the .designated .time . . AP® Chemistry Exam Regul\brly Scheduled Ex\bm D\bte: Mond\by morning, M\by 5, 2014 L\bte-Testing Ex\bm D\bte: Thursd\by \bfternoon, M\by 22, 2014 Section I Tot\bl Time: 1 hr. 30 min. Section II Tot\bl Time: 1 hr. 30 min.

42 Chemistry If you are giving the regularly sche\bule\b exam, say: It is Monday morning, May 5, and you will be taking the AP Chemistry Exam. If you are giving the alternate exam for late testing, say: It is Thursday afternoon, May 22, and you will be taking the AP Chemistry Exam. In a moment, you will open the packet that contains your exam materials. By opening this packet, you agree to all of the AP Program’s policies and procedures outlined in the 2013-14 Bulletin for AP Students and Parents. \bou may now remove the shrinkwrap from your exam packet and take out the Section I booklet, but do not open the booklet or the shrinkwrapped Section II materials. Put the white seals aside. . . . Carefully remove the AP Exam label found near the top left of your exam booklet cover. Now place it on page 1 of your answer sheet on the light blue box near the top right-hand corner that reads “AP Exam Label.” If .students .accidentally .place .the .exam .label .in .the .space .for .the .number .label .or .vice .versa, .advise . them .to .leave .the .labels .in .place . .They .should .not .try .to .remove .the .label; .their .exam .will .be . processed .correctly . . Read the statements on the front cover of Section I and look up when you have finished. . . . Sign your name, and write today’s date. Look up when you have finished. . . . Now print your full legal name where indicated. Are there any questions? . . . Turn to the back cover and read it completely. Look up when you have finished. . . . Are there any questions? . . . Section I is the multiple-choice portion of the exam. \bou may never discuss these specific multiple-choice questions at any time in any form with anyone, including your teacher and other students. If you disclose these questions through any means, your AP Exam score will be canceled. Are there any questions? . . . \bou must complete the answer sheet using a No. 2 pencil only. Mark all of your responses beginning on page 2 of your answer sheet, one response per question. Completely fill in the circles. If you need to erase, do so carefully and completely. No credit will be given for anything written in the exam booklet. Scratch paper is not allowed, but you may use the margins or any blank space in the exam booklet for scratch work. Calculators are not allowed for this section. Please put your calculators under your chair. Are there any questions? . . . \bou have 1 hour and 30 minutes for this section. Open your Section I booklet and begin.

43 AP Exam Instructio\Bns ???? 126 3 9 .Note .Start .Time .here . . .Note .Stop .Time .here . . .Check .that .students .are . marking .their .answers .in .pencil .on .their .answer .sheets, .and .that .they .are .not .looking .at .their . shrinkwrapped .Section .II .booklets . .After .1 .hour .and .30 .minutes, .say: Stop working. Close your booklet and put your answer sheet on your desk, face up. Make sure you have your AP number label and an AP Exam label on page 1 of your answer sheet. I will now collect your answer sheet. Collect .an .answer .sheet .from .each .student . .Check .that .each .answer .sheet .has .an .AP .number .label . and .an .AP .Exam .label . .Then .say: Now you must seal your exam booklet. Remove the white seals from the backing and press one on each area of your exam booklet cover marked “PLACE SEAL HERE.” Fold each seal over the back cover. When you have finished, place the booklet on your desk, face up. I will now collect your Section I booklet. . . . Collect .a .Section .I .booklet .from .each .student . .Check .that .each .student .has .signed .the .front .cover . of .the .sealed .Section .I .booklet . There .is .a .10-minute .break .between .Sections .I .and .II . .When .all .Section .I .materials .have .been . collected .and .accounted .for .and .you .are .ready .for .the .break, .say: Please listen carefully to these instructions before we take a 10-minute break. Everything you placed under your chair at the beginning of the exam must stay there. Leave your shrinkwrapped Section II packet on top of your desk during the break. \bou are not allowed to consult teachers, other students, or textbooks about the exam during the break. \bou may not make phone calls, send text messages, check email, use a social networking site, or access any electronic or communication device. Remember, you are not allowed to discuss the multiple-choice section of this exam. If you do not follow these rules, your score could be canceled. Are there any questions? . . . 12 6 3 9 .\bou may begin your break. Testing will resume at . . SECTION II: Free Response After .the .break, .say: May I have everyone’s attention? Place your Student Pack on your desk. . . . \bou may now remove the shrinkwrap from the Section II packet, but do not open the exam booklet until you are told to do so. . . . Read the bulleted statements on the front cover of the exam booklet. Look up when you have finished. . . . Now place an AP number label on the shaded box. If you don’t have any AP number labels, write your AP number in the box. Look up when you have finished. . . . Read the last statement. . . .

44 Chemistry Using your pen, print the first, middle and last initials of your legal name in the boxes and print today’s date where indicated. This constitutes your signature and your agreement to the statements on the front cover. . . . Turn to the back cover and complete Item 1 under “Important Identification Information.” Print the first two letters of your last name and the first letter of your first name in the boxes. Look up when you have finished. . . . In Item 2, print your date of birth in the boxes. . . . In Item 3, write the school code you printed on the front of your Student Pack in the boxes. . . . Read Item 4. . . . Are there any questions? . . . I need to collect the Student Pack from anyone who will be taking another AP Exam. \bou may keep it only if you are not taking any other AP Exams this year. If you have no other AP Exams to take, place your Student Pack under your chair now. . . . While Student Packs are being collected, read the information on the back cover of the exam booklet. Do not open the exam booklet until you are told to do so. Look up when you have finished. . . . Collect .the .Student .Packs . .Then .say: . Are there any questions? . . . Calculators may be used for Section II. \bou may get your calculators from under your chair and place them on your desk. . . . \bou have 1 hour and 30 minutes to complete Section II. \bou are responsible for pacing yourself, and you may proceed freely from one question to the next. \bou must write your answers in the exam booklet using a pen with black or dark blue ink or a No. 2 pencil. If you use a pencil, be sure that your writing is dark enough to be easily read. If you need more paper during the exam, raise your hand. At the top of each extra piece of paper you use, be sure to write only your AP number and the number of the question you are working on. Do not write your name. Are there any questions? . . . \bou may begin. 126 3 9 .Note .Start .Time .here . . .Note .Stop .Time .here . . .Check .that .students . are .writing .their .answers .in .their .exam .booklets . .Proctors .should .also .make .sure .that .Hewlett- Packard .calculators’ .infrared .ports .are .not .facing .each .other .and .that .students .are .not .sharing . calculators . .After .1 .hour .and .20 .minutes, .say: . There are 10 minutes remaining.

45 AP Exam Instructio\Bns CHEMISTRY After .10 .minutes, .say: Stop working and close your exam booklet. Place it on your desk, face up. . . . If .any .students .used .extra .paper .for .the .free-response .section, .have .those .students .staple .the .extra . sheet/s .to .the .first .page .corresponding .to .that .question .in .their .exam .booklets . .Then .say: Remain in your seat, without talking, while the exam materials are collected. . . . Collect .a .Section .II .booklet .from .each .student . .Check .for .the .following: . • .Exam .booklet .front .cover: .The .student .placed .an .AP .number .label .on .the .shaded .box, .and . pr inted .his .or .her .initials .and .today’s .date . . • .Exam .booklet .back .cover: .The .student .completed .the .“Important .Identification . In formation” .area . When .all .exam .materials .have .been .collected .and .accounted .for, .return .to .students .any .electronic . devices .you .may .have .collected .before .the .start .of .the .exam . . If you are giving the regularly sche\bule\b exam, say: \bou may not discuss or share these specific free-response questions with anyone unless they are released on the College Board website in about two days. \bour AP score results will be available online in July. If you are giving the alternate exam for late testing, say: None of the questions in this exam may ever be discussed or shared in any way at any time. \bour AP score results will be available online in July. If .any .students .completed .the .AP .number .card .at .the .beginning .of .this .exam, .say: Please remember to take your AP number card with you. \bou will need the information on this card to view your scores and order AP score reporting services online. Then .say: \bou are now dismissed. All .exam .materials .should .be .put .in .secure .storage .until .they .are .returned .to .the .AP .Program . after .your .school’s .last .administration . .Before .storing .materials, .check .the .“School .Use .Only” . section .on .page .1 .of .the .answer .sheet .and: . . • . . • .Fill .in .the .appropriate .section .number .circle .in .order .to .access .a .separate .AP . . In structional .Planning .Report .(for .regularly .scheduled .exams .only) .or .subject . . score .roster .at .the .class .section .or .teacher .level . .See .“Post-Exam .Activities” .in .the . . 2013-14 AP Coor\binator’s Manual . Check .your .list .of .students .who .are .eligible .for .fee .reductions .and .fill .in .the . . ap propriate .circle .on .their .registration .answer .sheets . .

Student Answer Sheet for the Multiple -Choice Section Use this section to capture student responses. (Note that the following answer sheet is a sample, and may differ from one used in an actual exam. )

Sign your legal name as it will\. appear on your college applic\.ations. Date To maintain the security of the exam and the validity of my AP score, \b will allow no one else to see the multiple-choice questions. \b will seal the multiple-choice booklet when asked to do so, and \b will not discuss these questions with anyone at any time after completing the section. \b am aware of and agree to the AP Program’s policies and procedures as outlined in the 2013-14 Bulletin for AP Students and Parents, including using testing accommodations (e.g., extended time, computer, etc.) only if \b have been preapproved by College Board Services for Students with \vDisabilities.COMPLETE THIS AREA AT EVERY EXAM. USE NO. 2 PENCIL ONLY A. SIGNATURE GE 1AP anuyC\bFu \bGHI JKLMFueHNOPMQuluRMMTIHOU\. anu.VFGHLu \bGHIuJKLMFueOVWHQOun\bNTU OHHZeuLHY 1 X B Q – a D Rpu yAa u.agy iFPOu\b2MXOLM2ZHX3u4Lp3ullp H5\bIu6PLXOu.\bFHu7u6PLXOuBDu HOOHLX H5\bIu \bXOu.\bFHu7u6PLXOuB8u HOOHLX gl A A A A A A A A A A A A A A A B B B B B B B B B B B B B B B C C C C C C C C C C C C C C C D D D D D D D D D D D D D D D \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b F F F F F F F F F F F F F F F G G G G G G G G G G G G G G G H H H H H H H H H H H H H H H I I I I I I I I I I I I I I I J J J J J J J J J J J J J J J K K K K K K K K K K K K K K K L L L L L L L L L L L L L L L M M M M M M M M M M M M M M M N N N N N N N N N N N N N N N O O O O O O O O O O O O O O O P P P P P P P P P P P P P P P Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q R R R R R R R R R R R R R R R S S S S S S S S S S S S S S S T T T T T T T T T T T T T T T U U U U U U U U U U U U U U U V V V V V V V V V V V V V V V W W W W W W W W W W W W W W W X X X X X X X X X X X X X X X Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z – – – – – – – – – – – – – 1 2 3 4 5 6 7 8 9 A A A A A A A A A A A A A B B B B B B B B B B B B B C C C C C C C C C C C C C D D D D D D D D D D D D D \b \b \b \b \b \b \b \b \b \b \b \b \b F F F F F F F F F F F F F G G G G G G G G G G G G G H H H H H H H H H H H H H I I I I I I I I I I I I I J J J J J J J J J J J J J K K K K K K K K K K K K K L L L L L L L L L L L L L M M M M M M M M M M M M M N N N N N N N N N N N N N O O O O O O O O O O O O O P P P P P P P P P P P P P Q Q Q Q Q Q Q Q Q Q Q Q Q R R R R R R R R R R R R R S S S S S S S S S S S S S T T T T T T T T T T T T T U U U U U U U U U U U U U V V V V V V V V V V V V V W W W W W W W W W W W W W X X X X X X X X X X X X X Y Y Y Y Y Y Y Y Y Y Y Y Y Z Z Z Z Z Z Z Z Z Z Z Z Z – – – – – – – – – – 0 0 0 0 0 0 0 0 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 2 3 3 3 3 3 3 3 3 4 4 4 4 4 4 4 4 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 0 0 1 1 2 2 3 3 4 5 6 7 8 9 6 12 7 1 8 2 9 3 10 4 11 5 0 0 0 0 0 0 0 0 0 0 1 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 2 2 2 3 3 3 3 3 3 3 3 3 3 4 4 4 4 4 4 4 4 4 4 5 5 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 9 S 9puuywagu9aoy Spuuticmuanu.cgRym Month AM PM F. MULTIPLE-CHOICE BOOKL\NET SERIAL NUMBER rpuuanuywaguluagu oahl.Aucel.Auorleu a.exymueryyo \bxam Name: Form Code: Form: COMPLETE THIS AREA ONLY ONCE. SCHOOL USE ONLY Fee Reduction Gr\bnted Section Number Option 1 Option 2 E. EXAM START TIME 0 0 1 1 2 3 4 5 6 7 8 9 1 2 773898 0 0 0 1 1 1 2 2 2 3 3 3 4 4 4 5 5 5 6 6 6 7 7 7 8 8 8 9 9 9 G. ONLINE PROVIDER CODE Day 0 0 0 0 0 0 0 0 0 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 2 2 3 3 3 3 3 3 3 3 3 4 4 4 4 4 4 4 4 4 5 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 L. SOCIAL SECURITY NUMBER (Option\bl) 99735-00657• UNLW\bB114 Q3779/1-4 COLLEGE CODE 0 0 0 0 1 1 1 1 2 2 2 2 3 3 3 3 4 4 4 4 5 5 5 5 6 6 6 6 7 7 7 7 8 8 8 8 9 9 9 9 M. COLLEGE TO RECEIVE YOUR AP SCORE REPORT College Name State Country Using the college \.code listed in the AP Student Pack, indicate the ONE college that you want to receive your AP score report. City SCHOOL CODE 0 0 0 0 0 0 1 1 1 1 1 1 2 2 2 2 2 2 3 3 3 3 3 3 4 4 4 4 4 4 5 5 5 5 5 5 6 6 6 6 6 6 7 7 7 7 7 7 8 8 8 8 8 8 9 9 9 9 9 9 School Name State Country J. SCHOOL YOU ATTEND City 0 0 0 0 0 0 0 0 0 0 1 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 2 2 2 3 3 3 3 3 3 3 3 3 3 4 4 4 4 4 4 4 4 4 4 5 5 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 9 INTERNATIONAL PHONE I. AREA CODE AND PHONE NUMBER 0 0 0 0 1 1 1 1 2 2 2 2 3 3 3 3 4 4 4 5 5 5 6 6 6 7 7 7 8 8 8 9 9 9 Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec Month Day Year K. DATE OF BIRTH .puuScmmy.ou Ama9yu ysy Not yet in 9th grade 9th 10th 11th 12th No longer in high school B123456789T

P. LANGUAGE — Do not complete this section unle\Nss instructed to do so. 1 2 34 5 67 8 9 A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I A B C D \b F G H I If this \bnswer sheet is for the French L\bngu\bge \bnd Culture, Germ\bn L\bngu\bge \bnd Culture, It\bli\bn L\bngu\bge \bnd Culture, Sp\bnish L\bngu\bge \bnd Culture, or Sp\bnish Liter\bture \bnd Culture Ex\bm, ple\bse \bnswer the following questions. Your responses will not \bffect your score. 1. Have you lived or studied for one month or mo\.re in a country where the language of \.the exam you are now taking is spoken? Yes No DO NOT WRITE IN THIS AREA O. SURVEY QUESTIONS — Answer the survey questions in the \NAP Student P\bck. Do not put responses to ex\bm questions in this\N section. PAGE 2 COMPLETE THIS AREA AT EACH EXAM (IF APPLICABLE) Indic\bte your \bnswers to the ex\bm questions in this\N section (p\bges 2 \bnd 3). M\brk only one response per question\N. If \b question h\bs onl\Ny four \bnswer options, do not m\brk option E. Answers written in the multiple-choice booklet will not be scored. A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b A B C D \b 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 5051 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 QUESTIONS 1–75 Yes No 2. Do you regularly speak or hear th\.e language at home\.? L GL 1L xL 2 L GL 1L xL 2 You must use \b No. 2 pencil \bnd m\brks must be complete. Do not use \b mech\bnic\bl pencil. It is very important that you fill in the entire circle darkly and completely. If you change your response, erase as completely as possible. Incomplete marks or erasures may affect your score. COMPLETE MARK EXAMPLES OF INCOMPLETE MARKS

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ZIP OR POSTAL CODECOUNTRY CODE PAGE 4 STREET ADDRESS (include street number, street name, apartment number, etc.) CITY A A A A A A A A A A A A A A A A A A A A A A A A A A B B B B B B B B B B B B B B B B B B B B B B B B B B C C C C C C C C C C C C C C C C C C C C C C C C C C D D D D D D D D D D D D D D D D D D D D D D D D D D \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b \b F F F F F F F F F F F F F F F F F F F F F F F F F F G G G G G G G G G G G G G G G G G G G G G G G G G G H H H H H H H H H H H H H H H H H H H H H H H H H H I I I I I I I I I I I I I I I I I I I I I I I I I I J J J J J J J J J J J J J J J J J J J J J J J J J J K K K K K K K K K K K K K K K K K K K K K K K K K K L L L L L L L L L L L L L L L L L L L L L L L L L L M M M M M M M M M M M M M M M M M M M M M M M M M M N N N N N N N N N N N N N N N N N N N N N N N N N N O O O O O O O O O O O O O O O O O O O O O O O O O O P P P P P P P P P P P P P P P P P P P P P P P P P P Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q Q R R R R R R R R R R R R R R R R R R R R R R R R R R S S S S S S S S S S S S S S S S S S S S S S S S S S T T T T T T T T T T T T T T T T T T T T T T T T T T U U U U U U U U U U U U U U U U U U U U U U U U U U V V V V V V V V V V V V V V V V V V V V V V V V V V W W W W W W W W W W W W W W W W W W W W W W W W W W X X X X X X X X X X X X X X X X X X X X X X X X X X Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Y Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z Z 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 / / / / / / / / / / / / / / / / / / / / / / / / A A A A A A A A A A A A A B B B B B B B B B B B B B C C C C C C C C C C C C C D D D D D D D D D D D D D \b \b \b \b \b \b \b \b \b \b \b \b \b F F F F F F F F F F F F F G G G G G G G G G G G G G H H H H H H H H H H H H H I I I I I I I I I I I I I J J J J J J J J J J J J J K K K K K K K K K K K K K L L L L L L L L L L L L L M M M M M M M M M M M M M N N N N N N N N N N N N N O O O O O O O O O O O O O P P P P P P P P P P P P P Q Q Q Q Q Q Q Q Q Q Q Q Q R R R R R R R R R R R R R S S S S S S S S S S S S S T T T T T T T T T T T T T U U U U U U U U U U U U U V V V V V V V V V V V V V W W W W W W W W W W W W W X X X X X X X X X X X X X Y Y Y Y Y Y Y Y Y Y Y Y Y Z Z Z Z Z Z Z Z Z Z Z Z Z A A A A A A A A A B B B B B B B B B C C C C C C C C C D D D D D D D D D \b \b \b \b \b \b \b \b \b F F F F F F F F F G G G G G G G G G H H H H H H H H H I I I I I I I I I J J J J J J J J J K K K K K K K K K L L L L L L L L L M M M M M M M M M N N N N N N N N N O O O O O O O O O P P P P P P P P P Q Q Q Q Q Q Q Q Q R R R R R R R R R S S S S S S S S S T T T T T T T T T U U U U U U U U U V V V V V V V V V W W W W W W W W W X X X X X X X X X Y Y Y Y Y Y Y Y Y Z Z Z Z Z Z Z Z Z 0 0 0 0 0 0 0 0 0 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2 2 2 3 3 3 3 3 3 3 3 3 4 4 4 4 4 4 4 4 4 5 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 / / / / / / / 0 0 0 1 1 1 2 2 2 3 3 3 4 4 4 5 5 5 6 6 6 7 7 7 8 8 8 9 9 9 Q. 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Section I: Multiple -Choice Questions This is the multiple -choice section of the 2014 AP exam. It includes cover material and other administrative instructions to help familiarize students with the mechanics of the exam. (Note that future exams may differ in look from the following content.)

AtaGlance Total Time1 hour, 30 minutes Number of Questions50 Percent of Total Score50% Writing InstrumentPencil required Electronic DeviceNone allowed Instructions SectionIofthisexam contains 50 multiple-choice questions .Fill in onlythecircles for numbers1through 50 on youranswer sheet.Pages containingaperiodic tableandlists containing equationsandconstants arealso printed in thisbooklet . Indicate all ofyouranswers to themultiple -choice questions on theanswer sheet.No credit will be givenforanything written in thisexam booklet ,but you may usethebooklet for notes or scratchwork.After youhave decided which of thesuggested answers is best, completely fill inthecorresponding circle ontheanswer sheet. Because thissection offersonlyfouranswer options foreach question ,do not mark the ( E ) answer circleforany question .Give onlyoneanswer to eachquestion .If you change an answer ,be sure thattheprevious mark iserasedcompletely .Here i sasample question and answer . Useyour timeeffectively ,working as quickly asyoucanwithout losingaccuracy .Do not spend toomuch time on anyone question .Go on to otherquestions andcome back to the ones youhave notanswered if youhave time.It is notexpected thateveryone will know theanswers to all ofthemultiple-choice questions. Your totalscore on SectionIis basedonly on thenumber of questionsansweredcorrectly. Points arenot deducted forincorrect answers or unanswered questions. DO NOT OPEN THIS BOOKLET UNTIL YOU ARE TOLD TO DO SO. AP ® Chemistry Exam SECTION I: Multiple Choice 2014

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-3- AP ¥ CHEMISTRY EQUATIONS AND CONSTANTS Throughout the exam the following symbols have the definitions specified unless otherwise noted. L, mL = liter(s), milliliter(s) mm Hg = millimeters of mercury g = gram(s) J, kJ = joule(s), kilojoule(s) nm = nanometer(s) V = volt(s) atm = atmosphere(s) mol = mole(s) ATOMIC STRUCTURE E = h ν c = λν E = energy ν = frequency λ = wavelength Planck’s constant, h = 6.626 × 10 −34 Js Speed of light, c = 2.998 × 10 8 ms −1 Avogadro’s number = 6.022 × 10 23 mol − 1 Electron charge, e = −1.602 × 10 −19 coulomb EQUILIBRIUM Kc = [C] [D] [A] [B] cd ab , where a A + b B R c C + d D Kp = CD AB()( )()() c a PPPP d b Ka = [H ][A ] [HA]  Kb = [OH ][HB ] [B]  Kw = [H +][OH −] = 1.0 ×10 −14 at 25 °C = K a × K b pH = −log [H +] , pOH = −log [OH −] 14 = pH + pOH pH = p K a + log [A ] [HA]  p K a = −log K a, pK b = −log K b Equilibrium Constants Kc (molar concentrations) Kp (gas pressures) K a (weak acid) Kb (weak base) Kw (water) KINETICS ln[A] t − ln[A] 0 = −kt >@ >@ 0 AA 11 t  = kt t ½ = 0.693 k k = rate constant t = time t ½ = half-life

-4- GASES, LIQUIDS, AND SOLUTIONS PV = nRT PA = P total × X A, where X A = moles A total moles Ptotal = P A + P B + P C + . . . n = m M K = °C + 273 D = m V KE per molecule = 1 2mv 2 Molarity, M = moles of solute per liter of solution A = abc P = pressure V = volume T = temperature n = number of moles m = mass M = molar mass D = density KE = kinetic energy v = velocity A = absorbance a = molar absorptivity b = path length c = concentration Gas constant, R = 8.314 J mol −1K−1 = 0.08206 L atm mol −1 K−1 = 62.36 L torr mol −1 K−1 1 atm = 760 mm Hg = 760 torr STP = 273.15 K and 1.0 atm THERMODYNAMICS / ELECTROCHEMISTRY q = mc∆T ∆ S° = p roducts reactants S  Ç D S Ç D ∆H° = products reactantsfH D  ÇÇ D fH D D ∆G ° = products reactantsfG D  ÇÇ D fG D D ∆G ° = ∆H° − T ∆S ° = −RT ln K = −n E° I = q t q = heat m = mass c = specific heat capacity T = temperature S ° = standard entropy H ° = standard enthalpy G° = standard Gibbs free energy n = number of moles E ° = standard reduction potential I = current (amperes) q = charge (coulombs) t = time (seconds) Faraday’s constant, = 96,485 coulombs per mole of electrons 1 volt = 1 joule 1 coulomb

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -5- CHEMISTRY Section I 50 Questions Time—90 minutes CALCULATORS ARE NOT ALLOWED FOR SECTION I. Note: For all questions, assume that the temperature is 298 K , the pressure is 1.0 atm, and solutions are aqueous unless otherwise specified. Directions: Each of the questions or incomplete statements below is followed by four suggested answers or completions. Select the one that is best in each case and then fill in the corresponding circle on the answer sheet. Compound Molar Mass (grams) Na 2O 62.0 MgO 40.3 K2O 94.2 CaO 56.1 1. According to the information in the table above, a 1.00 g sample of which of the following contains the greatest mass of oxygen? (A) Na 2O (B) MgO (C) K2O (D) CaO 2. Which of the following could be the identity of a white crystalline solid that exhibits the following properties? • It melts at 320 ∞C. • It does not conduct electricity as a solid. • It conducts electricity in an aqueous solution. (A) C6H12O6( s) (B) NaOH(s) (C) SiO 2(s) (D) Cu(s) 3. Which of the following correctly identifies which has the higher first-ionization energy, Cl or Ar, and supplies the best justification? (A) Cl, because of its higher electronegativity (B) Cl , because of its higher electron affinity (C) Ar, because of its completely filled valence shell (D) Ar , because of its higher effective nuclear charge

Unauthorized copying or reuse of any part of this page is illegal. GO ON T O THE NEXT PAGE. -6- 2 BaO 2( s) Æ ¨ 2 BaO( s) + O 2(g ) D H ∞ = 162 kJ/mol rxn 4. A sealed rigid vessel contains BaO 2(s) in equilibrium with BaO(s) and O2( g ) as represented by the equation above. Which of the following changes will increase the amount of BaO 2( s) in the vessel? (A) Removing a small amount of O2( g ) (B) Removing a small amount of BaO( s) (C) Adding He gas to the vessel (D) Lowering the temperature 5. Which of the following best helps to explain why the value of Δ H ° for the dissolving of CaF 2 in water is positive? (A) CaF 2(s) is insoluble in water. (B) CaF 2( s) dissolves in water to form CaF 2(aq) particles. (C) Ca 2+ ions have very strong ion-ion interactions with F− ions in the crystal lattice. (D) Ca 2+ ions have very strong ion-dipole interactions with water molecules in the solution.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -7- 6. Under which of the following conditions of temperature and pressure will H2 gas be expected to behave most like an ideal gas? (A) 50 K and 0.10 atm (B) 50 K and 5.0 atm (C) 500 K and 0.10 atm (D) 500 K and 50 atm 7. The volume of a sample of air in a cylinder with a movable piston is 2.0 L at a pressure P1, as shown in the diagram above. The volume is increased to 5.0 L as the temperature is held constant. The pressure of the air in the cylinder is now P2. What effect do the volume and pressure changes have on the average kinetic energy of the molecules in the sample? (A) The average kinetic energy increases. (B) The average kinetic energy decreases. (C) The average kinetic energy stays the same. (D) It cannot be determined how the kinetic energy is affected without knowing P1 and P2.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -8- Questions 8-10 refer to the following. M+ is an unknown metal cation with a +1 charge. A student dissolves the chloride of the unknown metal, MCl, in enough water to make 100.0 mL of solution. The student then mixes the solution with excess AgNO 3 solution, causing AgCl to precipitate. The student collects the precipitate by filtration, dries it, and records the data shown below. (The molar mass of AgCl is 143 g/mol.) Mass of unknown chloride, MCl 0.74 g Mass of filter paper 0.80 g Mass of filter paper plus AgCl precipitate 2.23 g 8. What is the identity of the metal chloride? (A) NaCl (B) KCl (C) CuCl (D) LiCl 9. During the course of the experiment, which of the following happens to the NO 3 - ions? (A) They are oxidized by Cl - ions. (B) They are reduced to NO 2 - ions. (C) They are decomposed by reacting with M + ions. (D) They remain dissolved in the filtrate solution.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -9- 10. Which of the following diagrams best represents the AgNO 3 solution before the reaction occurs? Note: water molecules are represented by the symbol . (A) (B) (C) (D)

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -10- 11. When 200. mL of 2.0 M NaOH(aq) is added to 500. mL of 1.0 M HCl(aq), the pH of the resulting mixture is closest to (A) 1.0 (B) 3.0 (C) 7.0 (D) 13.0 Element First Ionization Energy (kJ/mol) Atomic Radius (pm) B 801 85 C 1086 77 N 1400 75 O 1314 73 F 1680 72 Ne 2080 70 12. The table above shows the first ionization energy and atomic radius of se veral elements. Which of the following best helps to explain the deviation of the first ionization energy of oxygen from the overall trend? (A) The atomic radius of oxygen is greater than the atomic radius of fluorine. (B) The atomic radius of oxygen is less than theatomic radius of nitrogen. (C) There is repulsion between paired electrons in oxygen’s 2p orbitals. (D) There is attraction between paired electrons in oxygen’s 2p orbitals. 13. Which of the following equations represents a reaction for which the standard entrop y change is positive (DS ° > 0) ? (A) 3 O 2(g ) → 2 O 3(g ) (B) 2 H 2(g ) + O 2(g ) → 2 H 2O(l) (C) CaCO 3(s) → CaO( s) + CO 2(g ) (D) I2(g ) + 2 K( s) → 2 KI( s)

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -11- Questions 14-16 refer to the following. The table below contains information about samples of four different gases at 273 K. The samples are in four identical rigid containers numbered 1 throug h 4. Container Gas Pressure(atm) Mass of Sample (g) 1 He 2.00 ? 2 Ne 2.00 ? 3 ? 2.00 16.0 4 SO 2 1.96 64.1 14. On the basis of the data provided above, the gas in container 3 could be (A) CH 4 (B) O2 (C) Ar (D) CO 2 15. Under the conditions given, consider co ntainers 1, 2, and 4 only. The average speed of the gas particles is (A) greatest in container 1 (B) greatest in container 2 (C) greatest in container 4 (D) the same in containers 1, 2, and 4 16. The best explanation for the lower pressure in container 4 is that SO 2 molecules (A) have a larger averag e speed than the other three gases (B) occupy a larger portion of the container volume than the other three gases (C) have stronger intermol ecular attractions than the other three gases (D) contain π bonds, while the other gases contain only σ bonds

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -12- 17. The potential energy as a function of internuclear distance for three diatomic molecules, X2, Y 2, and Z 2, is shown in the graph above. Based on the data in the graph, which of the following correctly identifies the diatomic molecules, X2, Y2, and Z2? X 2 Y2 Z2 (A) H 2 N2 O2 (B)H 2 O 2 N2 (C) N 2 O 2 H 2 (D) O 2 H 2 N 2

Unauthorized copying or reuse of any part of this page is illegal. == GO ON TO THE NEXT PAGE. -13-= 18. A 10. g cube of copper at a temperature T1 is placed in an insulated cup containing 10. g of water at a temperature T2. If T1 > T 2, which of the following is true of the system when it has attained thermal equilibrium? (The specific heat of copper is 0.385 J/(g·°C) and the specific heat of water is 4.18 J/(g·°C).) (A) The temperature of the copper changed more than the temperature of the water. (B) The temperature of the water changed more than the temperature of the copper. (C) The temperature of the water and the copper changed by the same amount. (D) The relative temperature ch anges of the copper and the water cannot be determined without knowing T1 and T2. 19. A solution containing HCl and the weak acid HClO 2 has a pH of 2.4. Enough KOH(aq) is added to the solution to increase the pH to 10.5. The amount of which of the following species increases as the KOH(aq) is added? (A) Cl -(aq) (B) H+(aq) (C) ClO 2 -( aq) (D) HClO 2(aq) 2 H 2O(l ) Æ ¨ H 3O+( aq) + OH -(aq) 20. The autoionization of water is represented by the equation above. Values of pK w at various temperatures are listed in the table below. Temperature ( ∞C) pK w 0 14.9 10 14.5 20 14.2 30 13.8 40 13.5 Based on the information above, which of the following statements is true? (A) The dissociation of water is an exothermic process. (B) The pH of pure water is 7.00 at any temperature. (C) As the temperature increases, the pH of pure water increases. (D) As the temperature increases, the pH of pure water decreases.

Unauthorized copying or reuse of any part of this page is illegal. == GO ON TO THE NEXT PAGE. -14-= Questions 21-24 refer to the following information. CO(g ) + 2 H 2(g ) ¨ CH 3OH(g ) DH < 0 Æ The synthesis of CH 3OH(g ) from CO(g) and H2(g ) is represented by the equation above. The value of Kc for the reaction at 483 K is 14.5. 21. Which of the following explains the effect on the equilibrium constant, Kc, when the temperature of the reaction system is increased to 650 K? (A) Kc will increase because the activation energy of the forward reaction increases more than that of the reverse reaction. (B) K c will increase because there are more reactant molecules than product molecules. (C) Kc will decrease because the reaction is exothermic. (D) Kc is constant and will not change. 22. A 1.0 mol sample of CO( g) and a 1.0 mol sample of H2(g ) are pumped into a rigid, previously evacuated 2.0 L reaction vessel at 483 K. Which of the following is true at equilibrium? (A) [H 2] = 2[CO] (B) [H 2] < [CO] (C) [CO] = [CH 3OH] < [H 2] (D) [CO] = [CH 3OH] = [H 2] 23. A mixture of CO(g ) and H2(g ) is pumped into a previously evacuated 2.0 L reaction vessel. The total pressure of the reaction system is 1.2 atm at equilibrium. What will be the total pressure of the system if the volume of the reaction vessel is reduced to 1.0 L at constant temperature? (A) Less than 1.2 atm (B) Greater than 1.2 atm but le ss than 2.4 atm (C) 2.4 atm (D) Greater than 2.4 atm 24. Which of the following statements is true about bond energies in this reaction? (A) The energy absorbed as the bonds in the reactants are broken is greater than the energy released as the bonds in the product are formed. (B) The energy released as the bonds in the reactants are broken is greater than the energy absorbed as the bonds in the product are formed. (C) The energy absorbed as the bonds in the reactants are broken is less than the energy released as the bonds in the product are formed. (D) The energy released as the bonds in the reactants are broken is less than the energy absorbed as the bonds in the product are formed.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -15- 25. A solution is prepared by adding 100 mL of 1.0 M HC 2H3O2(aq) to 100 mL of 1.0 M NaC 2H3O2(aq). The solution is stirred and its pH is measur ed to be 4.73. After 3 drops of 1.0 M HCl are added to the solution, the pH of the solution is measured and is s till 4.73. Which of the following equations represents the chemical reaction that accounts for the fact that acid was added but there was no detectable change in pH? (A) H3O+(aq) + OH −(aq) Æ 2 H 2O(l) (B) H3O+(aq) + Cl −(aq) Æ HCl(g) + H 2O(l ) (C) H3O+(aq) + C 2H3O2 −( aq) Æ HC 2H3O2(aq) + H 2O( l) (D) H3O+( aq) + HC 2H3O2(aq ) Æ H 2C2H3O2+( aq) + H 2O(l )

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -16- MnO 4 − + 5 Fe 2+ + 8 H + Æ Mn 2+ + 5 Fe 3+ + 4 H 2O 26. In the reaction represented above, the number of MnO 4− ions that react must be equal to which of the following? (A) One-fifth the number of Fe 2+ ions that are consumed (B) Eight times the number of H+ ions that are consumed (C) Five times the number of Fe 3+ ions that are produced (D) One-half the number of H2O molecules that are produced 27. A student prepared five solutions of CuSO 4 with different concentrations, and then filled five cuvettes, each containing one of the solutions. The cuvettes were placed in a spectrophotometer set to the appropriate wavelength for maximum absorbance. The abso rbance of each solution was measured and recorded. The student plotted absorbance versus concentration, as show n in the figure above. Which of the following is the most likel y explanation for the variance of the data point for the 0.600 M CuSO 4 solution? (A) The cuvette into which the 0.600 M solution was placed had some water droplets inside. (B) The cuvette into which the 0.600 M solution was placed was filled slightly more than the other cuvettes. (C) The wavelength setting was accidentally moved away from that of maximum absorbance. (D) The cuvette used for the 0.600 M solution had not been wiped clean before being put in the spectrophotometer.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -17- X2 + Y 2 Æ X 2Y2 rate = k[X 2] 28. A reaction and its experimentally determined rate law are represented above. A chemist proposes two different possible mechanisms for the reaction, which are given below. Mechanism 1 X 2 Æ 2 X (slow ) X + Y 2 Æ XY 2 ( fast) X + XY 2 Æ X 2Y2 (fast ) Mechanism 2 X2 Æ 2 X ( slow) X + Y 2 Æ XY + Y ( fast) X + XY Æ X 2Y (fast) X 2Y + Y Æ X 2Y2 ( fast) Based on the information above, wh ich of the following is true? (A) Only mechanism 1 is consistent with the rate law. (B) Only mechanism 2 is consistent with the rate law. (C) Both mechanism 1 and mechanism 2 are consistent with the rate law. (D) Neither mechanism 1 nor mechanism 2 is consistent with the rate law. FeF 2(s) Æ ¨ Fe 2+( aq) + 2 F −(aq) K 1 = 2 × 10 −6 F−(aq) + H +(aq) Æ ¨ HF( aq) K 2 = 1 × 10 3 FeF 2( s) + 2 H +(aq) Æ ¨ Fe 2+( aq) + 2 HF( aq) K 3 = ? 29. On the basis of the information above, the dissolution of FeF 2(s) in acidic solution is (A) thermodynamically favorable, because K2 > 1 (B) thermodynamically favorable, because K3 > 1 (C) not thermodynamically favorable, because K1 < 1 (D) not thermodynamically favorable, because K3 < 1

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -18- 30. Thymine and adenine form a base pair in the DNA mo lecule. These two bases can form a connection between two strands of DNA via two hydrogen b onds. Which of the following diagrams shows the correct representation of the hydrogen bonding (denoted by dashed lines) between thymine and adenine base pairs? (In each diagram, thymine is shown at the left and adenine is shown at the right. The bases are attached to the backbone portion of the DNA strands.) (A) (B) (C) (D)

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -19- 31. A sample containing atoms of C and F was analyzed using x-ray photoelectron spectroscopy. The portion of the spectrum showing the 1 s peaks for atoms of the two elements is s hown above. Which of the following correctly identifies the 1s peak for the F atoms and provides an appropriate explanation? (A) Peak X, because F has a smaller first ionization energy than C has. (B) Peak X, because F has a greater nuclear charge than C has. (C) Peak Y, because F is more electronegative than C is. (D) Peak Y, because F has a smaller atomic radius than C has.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -20- Questions 32-34 refer to the following. 5 H 2O2( aq) + 2 MnO 4 −( aq) + 6 H +(aq ) Æ 2 Mn 2+(aq) + 8 H 2O(l ) + 5 O 2(g ) In a titration experiment, H 2O2( aq) reacts with aqueous MnO 4 -( aq ) as represented by the equation above. The dark purple KMnO 4 solution is added from a buret to a colorless, acidified solution of H2O2( aq) in an Erlenmeyer flask. (Note: At the end point of the titration, the solution is a pale pink color.) 32. At a certain time during the titration, the rate of appearance of O2( g ) was 1.0 ¥ 10 - 3 mol/(L s). What was the rate of disappearance of MnO 4 - at the same time? (A) 6.0 ¥ 10 - 3 mol/(L s) (B) 4.0 ¥ 10 - 3 mol/(L s) (C) 6.0 ¥ 10 mol/(L s) -4 (D) 4.0 10 mol/(L s) ¥ -4 33. Which element is being oxidized during the titration, and what is the element’s change in oxidation number? (A) Oxygen, which changes from - 1 to 0 (B) Oxygen, which changes from 0 to -2 (C) Manganese, which changes from -1 to +2 (D) Manganese, which changes from +7 to +2 34. Which of the following best describes what happens to the pH of the H2O2 solution as the titration proceeds? (A) The +2 charge on the manganese ions maintains the acidity of the solution. (B) The production of water dilutes the solution, making it basic. (C) As H+ ions are consumed, the solution becomes less acidic and the pH increases. (D) As H+ ions are consumed, the solution becomes less acidic and the pH decreases.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -21- 35. The BF 3 molecule is nonpolar, whereas the NF 3 molecule is polar. Which of the following statements accounts for the difference in polarity of the two molecules? (A) In NF 3, each F is joined to N with multiple bonds, whereas in BF 3, each F is joined to B with single bonds. (B) N − F bonds are polar, whereas B − F bonds are nonpolar. (C) NF 3 is an ionic compound, whereas BF 3 is a molecular compound. (D) Unlike BF 3, NF 3 has a nonplanar geometry due to an unshared pair of electrons on the N atom. PCl 3( g ) + Cl 2(g ) Æ PCl 5(g ) K c = 6.5 ¨ 36. At a certain point in time, a 1.00 L rigid reaction vessel contains 1.5 mol of PCl 3( g ) , 1.0 mol of Cl 2(g ) , and 2.5 mol of PCl 5(g ) . Which of the following describes how the measured pressure in the reaction vessel will change and why it will change that way as the reaction system approaches equilibrium at constant temperature? (A) The pressure will increase because Q < K c. (B) The pressure will increase because Q > K c. (C) The pressure will decrease because Q < K c. (D) The pressure will decrease because Q > K c. N2(g ) + 3 H 2(g ) Æ ¨ 2 NH 3( g ) 298H DD = −92 kJ/mol rxn ; 298G DD = − 33 kJ/mol rxn 37. Consider the reaction re presented above at 298 K. When equal volumes of N2( g ) and H2(g ), each at 1 atm, are mixed in a closed container at 298 K, no formation of NH 3( g ) is observed. Which of the following best explains the observation? (A) The N2( g ) and the H2(g ) must be mixed in a 1:3 ratio for a reaction to occur. (B) A high activation energy makes the forward reaction extremely slow at 298 K. (C) The reaction has an extremely small equilibrium constant, thus almost no product will fo rm. (D) The reverse reaction has a lower activation energy than the forward reaction, so the forward reaction does not occur.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -22- 38. Data collected during the titration of a 20.0 mL sample of a 0.10 M solution of a monoprotic acid with a solution of NaOH of unknown concentration are plotted in the graph above. Based on the data, which of the following are the approximate p K a of the acid and the molar concentration of the NaOH? p K a [NaOH] (A) 4.7 0.050 M (B) 4.7 0.10 M (C) 9.3 0.050 M (D) 9.3 0.10 M

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -23- Questions 39-41 refer to the following graph, wh ich shows the heating curve for methane, CH 4 . 39. How much energy is required to melt 64 g of methane at 90 K? (The molar mass of methane is 16 g/mol. ) (A) 0.24 kJ (B) 3.8 kJ (C) 33 kJ (D) 60. kJ 40. Which of the following best explains why more energy is required for the process occurring at 110 K than for the process occurring at 90 K ? (A) Intermolecular attractions are completely overcome during vaporization. (B) Intermolecular attractions in the solid phase are weaker than in the liquid phase. (C) Electron clouds of methane molecules are less polarizable at lower temperatures. (D) Vaporization involves a large increase in temperature. 41. The enthalpy of vaporizatio n of water is 40.7 kJ/mol. Which of the following best explains why the enthalpy of vaporization of methane is less than that of water? (A) Methane does not exhibit hydrogen bonding, but water does. (B) Methane has weaker dispersion forces. (C) Methane has a smaller molar mass. (D) Methane has a much lower density.

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -24- 42. Steel is an alloy consisting of Fe with a small amount of C. Elemental Cr can be added to steel to make the steel less likely to rust; Cr atoms react with oxygen in the air to form a nonreactive layer of chromium oxide on the surface of the steel, preventing the oxidation of underlying Fe atoms. A sample of steel-chromium alloy contains 15 percent Cr by mass. Which of the following diagrams best shows a particle-level view of a surface section and an interior section of the alloy represented below at the left? (T he atomic radii of the atoms involved are given in the table below at the right.) (A) (B) (C) (D)

Unauthorized copying or reuse of any part of this page is illegal. == GO ON TO THE NEXT PAGE. -25-= 43. Consider the reaction represented by the equation 2 X + 2 Z Æ X 2Z2. During a reaction in which a large excess of reactant X was present, the concentration of reactant Z was monitored over time. A plot of the natural logarithm of the concentration of Z versus time is shown in the figure above. The order of the reaction with respect to reactant Z is (A) zero order (B) first order (C) second order (D) third order

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -26- Questions 44-46 relate to the following information. XY 2 → X + Y 2 The equation above represents the decomposition of a compound XY 2. The diagram below shows two reaction profiles (path one and path two) for the decomposition of XY 2. 44. Which of the following most likely accounts for the difference between reaction path one and reaction path two? (A) A higher temperature in path one (B) A higher temperature in path two (C) The presence of a catalyst in path one (D) The presence of a catalyst in path two 45. Which of the following best describes the flow of heat when 1.0 mol of XY 2 decomposes? (A) 50 kJ of heat is transferred to the surroundings. (B) 50 kJ of heat is transferred from the surroundings. (C) 100 kJ of heat is transferred to the surroundings. (D) 100 kJ of heat is transferred from the surroundings. 46. The reaction is thermodynamically favorable under standard conditions at 298 K. Therefore, the value of Δ S° for the reaction must be (A) equal to zero (B) equal to D H °/ 298 K (C) greater than D H °/ 298 K (D) less than D H °/ 298 K

47. Which of the following diagrams best illustrates how a displacement in an ionic crystal results in cleavage and brittleness? Before Displacement After Displacement (A) (B) (C)   (D) Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -27-

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -28- C3H8( g ) + 4 Cl 2(g ) Æ C 3H4Cl 4(g ) + 4 HCl( g) 48. A 6.0 mol sample of C3H8(g ) and a 20. mol sample of Cl 2(g ) are placed in a previously evacuated vessel, where they react according to the equation above. After one of the reactants has been totally consumed, how many moles of HCl(g ) have been produced? (A) 4.0 mol (B) 8.0 mol (C) 20. mol (D) 24 mol Name Structural Formula Molar Mass (g/mol) Acetone 58.1 1-propanol 60.1 Butane 58.1 49. The table above shows the structural formulas and molar masses for three different co mpounds. Which of the following is a list of the compounds in order of increasing boiling points? (A) Butane < 1-propanol < acetone (B) Butane < acetone < 1-propanol (C) 1-propanol < acetone < butane (D) Acetone = butane < 1-propanol

Unauthorized copying or reuse of any part of this page is illegal. GO ON TO THE NEXT PAGE. -29- NO(g ) + NO 3(g ) → 2 NO 2(g ) rate = k[NO] [NO 3] 50. The reaction represented above occurs in a single step that involves the collision between a particle of NO and a particle of NO 3. A scientist correctly calculates the rate of collisions between NO and NO 3 that have sufficient energy to overcome the activation energy. The observed reaction rate is only a small fraction of the calculated collision rate. Which of the following best explains the discrepancy? (A) The energy of collisions between two reactant particles is frequently absorbed by collision with a third particle. (B) The two reactant particles must collide with a particular orientation in order to react. (C) The activation energy for a reaction is dependent on the concentrations of the reactant particles. (D) The activation energy for a reaction is dependent on the temperature.

Unauthorized copying or reuse of any part of this page is illegal. -30- S T O P END OF SECTION I IF YOU FINISH BEFORE TIME IS CALLED, YOU MAY CHECK YOUR WORK ON THIS SECTION. DO NOT GO ON TO SECTION II UNT IL YOU ARE TOLD TO DO SO. ________________________________ MAKE SURE YOU HAV E DONE THE FOLLOWING. • PLACED YOUR AP NUMBER LABEL ON YOUR ANSWER SHEET • WRITTEN AND GRIDDED YO UR AP NUMBER CORRECTLY ON YOUR ANSWER SHEET • TAKEN THE AP EXAM LABEL FR OM THE FRONT OF THIS BOOKLET AND PLACED IT ON YOUR ANSWER SHEET.

Section I I: Free- Response Questions This is the free-response section of the 2014 AP exam. It includes cover material and other administrative instructions to help familiarize students with the mechanics of the exam. (Note that future exams may differ in look from the following content.)

AP ® Chemistry Exam SECTION II: Free Response 2014 DO NOT OPEN THIS BOOKLET UNTIL YOU ARE TOLD TO DO SO. At a Glance Total Time 1 hour, 30 minutes Number of Questions 7 Percent of Total Score 50% Writing Instrument Either pencil or pen with black or dark blue ink Electronic Device Calculator allowed Suggested Time Approximately 20 minutes each for questions 1 – 3 and 7 minutes each for questions 4 – 7 Weight Approximate weights: Questions 1 – 3 22% each Instructions The questions for Section II are printed in this booklet . Pages containing a periodic table and lists containing equations and constants are also printed in this booklet . You may use the pages that the questions are printed on to organize your answers or for scratch work, but you must write your answers in the areas designated for each response. Only material written in the space provided will be scored . Examples and equations may be included in your responses where appropriate. For calculations, clearly show the method used and the steps involved in arriving at your answers. You must show your work to receive credit for your answer. Pay attention to significant figures. Write clearly and legibly. Cross out any errors you make; erased or crossed- out work will not be scored. Manage your time carefully. You may proceed freely from one question to the next. You may review your responses if you finish before the end of the exam is announced . Questions 4 – 7 9% each

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-3- AP ¥ CHEMISTRY EQUATIONS AND CONSTANTS Throughout the exam the following symbols have the definitions specified unless otherwise noted. L, mL = liter(s), milliliter(s) mm Hg = millimeters of mercury g = gram(s) J, kJ = joule(s), kilojoule(s) nm = nanometer(s) V = volt(s) atm = atmosphere(s) mol = mole(s) ATOMIC STRUCTURE E = h ν c = λν E = energy ν = frequency λ = wavelength Planck’s constant, h = 6.626 × 10 −34 Js Speed of light, c = 2.998 × 10 8 ms −1 Avogadro’s number = 6.022 × 10 23 mol − 1 Electron charge, e = −1.602 × 10 −19 coulomb EQUILIBRIUM Kc = [C] [D] [A] [B] cd ab , where a A + b B R c C + d D Kp = CD AB()( )()() c a PPPP d b Ka = [H ][A ] [HA]  Kb = [OH ][HB ] [B]  Kw = [H +][OH −] = 1.0 ×10 −14 at 25 ° C = K a × K b pH = −log [H +] , pOH = −log [OH −] 14 = pH + pOH pH = p K a + log [A ] [HA]  p K a = −log K a, pK b = −log K b Equilibrium Constants Kc (molar concentrations) Kp (gas pressures) K a (weak acid) Kb (weak base) Kw (water) KINETICS ln[A] t − ln[A] 0 = −kt >@ >@ 0 AA 11 t  = kt t ½ = 0.693 k k = rate constant t = time t ½ = half-life

-4- GASES, LIQUIDS, AND SOLUTIONS PV = nRT PA = P total × X A, where X A = moles A total moles Ptotal = P A + P B + P C + . . . n = m M K = °C + 273 D = m V KE per molecule = 1 2mv 2 Molarity, M = moles of solute per liter of solution A = abc P = pressure V = volume T = temperature n = number of moles m = mass M = molar mass D = density KE = kinetic energy v = velocity A = absorbance a = molar absorptivity b = path length c = concentration Gas constant, R = 8.314 J mol −1K−1 = 0.08206 L atm mol −1 K−1 = 62.36 L torr mol −1 K−1 1 atm = 760 mm Hg = 760 torr STP = 273.15 K and 1.0 atm THERMODYNAMICS / ELECTROCHEMISTRY q = mc∆T ∆ S° = p roducts reactants S  Ç D S Ç D ∆H° = products reactantsfH D  ÇÇ D fH D D ∆G ° = products reactantsfG D  ÇÇ D fG D D ∆G ° = ∆H° − T ∆S ° = −RT ln K = −n E° I = q t q = heat m = mass c = specific heat capacity T = temperature S ° = standard entropy H ° = standard enthalpy G° = standard Gibbs free energy n = number of moles E ° = standard reduction potential I = current (amperes) q = charge (coulombs) t = time (seco nds) Faraday’s constant, = 96,485 coulombs per mole of electrons 1 volt = 1 joule 1 coulomb

GO ON TO THE NEXT PAGE. -5- SECTION I I BEGINS ON P AGE 6.

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