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study guide with solutions manual for organic chemistry a short course 13th study guide with solutions manual for organic chemistry a short course 13th study guide with solutions manual for organic chemistry a short course 13th study guide with solutions manual for organic chemistry a short course 13th study guide with solutions manual for organic chemistry a short course 13th
Study Guide and Solutions Manual Organic Chemistry A Short Course THIRTEENTH EDITION David J Hart The Ohio State University Christopher M Hadad The Ohio State University Leslie E Craine Central Connecticut State University Harold Hart Michigan State University Prepared by David J Hart The Ohio State University Christopher M Hadad The Ohio State University Leslie E Craine Central Connecticut State University Harold Hart Michigan State University Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part This is an electronic version of the print textbook Due to electronic rights restrictions, some third party content may be suppressed Editorial review has deemed that any suppressed content does not materially affect the overall learning experience The publisher reserves the right to remove content from this title at any time if subsequent rights restrictions require it For valuable information on pricing, previous editions, changes to current editions, and alternate formats, please visit www.cengage.com/highered to search by ISBN#, author, title, or keyword for materials in your areas of interest Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part © 2012 Brooks/Cole, Cengage Learning ALL RIGHTS RESERVED No part of this work covered by the copyright herein may be reproduced, transmitted, stored, or used in any form or by any means graphic, electronic, or mechanical, including but not limited to photocopying, recording, scanning, digitizing, taping, Web distribution, information networks, or information storage and retrieval systems, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without the prior written permission of the publisher Proudly sourced and uploaded by [StormRG] Kickass Torrents | TPB | ET | h33t For product information and technology assistance, contact us at Cengage Learning Customer & Sales Support, 1-800-354-9706 For permission to use material from this text or product, submit all requests online at www.cengage.com/permissions Further permissions questions can be emailed to permissionrequest@cengage.com ISBN-13: 978-1-111-42585-2 ISBN-10: 1-111-42585-X Brooks/Cole 20 Davis Drive Belmont, CA 94002-3098 USA Cengage Learning is a leading provider of customized learning solutions with office locations around the globe, including Singapore, the United Kingdom, Australia, Mexico, Brazil, and Japan Locate your local office at: www.cengage.com/global Cengage Learning products are represented in Canada by Nelson Education, Ltd To learn more about Brooks/Cole, visit www.cengage.com/brookscole Purchase any of our products at your local college store or at our preferred online store www.cengagebrain.com Printed in the United States of America 14 13 12 11 10 Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Contents Introduction to the Student v Chapter Bonding and Isomerism Chapter Alkanes and Cycloalkanes; Conformational and Geometric Isomerism 19 Chapter Alkenes and Alkynes 37 Chapter Aromatic Compounds 61 Chapter Stereoisomerism 87 Chapter Organic Halogen Compounds; Substitution and Elimination Reactions 109 Chapter Alcohols, Phenols, and Thiols 123 Chapter Ethers and Epoxides 141 Chapter Aldehydes and Ketones 157 Chapter 10 Carboxylic Acids and Their Derivatives 187 Chapter 11 Amines and Related Nitrogen Compounds 211 Chapter 12 Spectroscopy and Structure Determination 233 Chapter 13 Heterocyclic Compounds 247 Chapter 14 Synthetic Polymers 263 Chapter 15 Lipids and Detergents 279 Chapter 16 Carbohydrates 291 Chapter 17 Amino Acids, Peptides, and Proteins 317 Chapter 18 Nucleotides and Nucleic Acids 345 Summary of Synthetic Methods 361 Summary of Reaction Mechanisms 375 Review Problems On Synthesis 381 Sample Multiple Choice Test Questions 385 © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part iii Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Introduction to the Student This study guide and solutions book was written to help you learn organic chemistry The principles and facts of this subject are not easily learned by simply reading them, even repeatedly Formulas, equations, and molecular structures are best mastered by written practice To help you become thoroughly familiar with the material, we have included many problems within and at the end of each chapter in the text It is our experience that such questions are not put to their best use unless correct answers are also available Indeed, answers alone are not enough If you know how to work a problem and find that your answer agrees with the correct one, fine But what if you work conscientiously, yet cannot solve the problem? You then give in to temptation, look up the answer, and encounter yet another dilemma–how in the world did the author get that answer? This solutions book has been written with this difficulty in mind For many of the problems, all of the reasoning involved in getting the correct answer is spelled out in detail Many of the answers also include cross-references to the text If you cannot solve a particular problem, these references will guide you to parts of the text that you should review Each chapter of the text is briefly summarized Whenever pertinent, the chapter summary is followed by a list of all the new reactions and mechanisms encountered in that chapter These lists should be especially helpful to you as you review for examinations When you study a new subject, it is always useful to know what is expected To help you, we have included in this study guide a list of learning objectives for each chapter—that is, a list of what you should be able to after you have read and studied that chapter Your instructor may want to delete items from these lists of objectives or add to them However, we believe that if you have mastered these objectives—and the problems should help you to this—you should have no difficulty with examinations Furthermore, you should be very well prepared for further courses that require this course as a prerequisite Near the end of this study guide you will find additional sections that may help you to study for the final examination in the course The SUMMARY OF SYNTHETIC METHODS lists the important ways to synthesize each class of compounds discussed in the text It is followed by the SUMMARY OF REACTION MECHANISMS Both of these sections have references to appropriate portions of the text, in case you feel that further review is necessary Finally, you will find two lists of sample test questions The first deals with synthesis, and the second is a list of multiple-choice questions Both of these sets should help you prepare for examinations In addition, we offer you a brief word of advice about how to learn the many reactions you will study during this course First, learn the nomenclature systems thoroughly for each new class of compounds that is introduced Then, rather than memorizing the particular examples of reactions given in the text, study reactions as being typical of a class of compounds For example, if you are asked how compound A will react with compound B, proceed in the following way First ask yourself: to what class of compounds does A belong? How does this class of compounds react with B (or with compounds of the general class to which B belongs)? Then proceed from the general reaction to the specific case at hand This approach will probably help you to eliminate some of the memory work often associated with organic chemistry courses We urge you to study regularly, and hope that this study guide and solutions book will make it easier for you to so © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part v vi Introduction to the Student Great effort has been expended to ensure the accuracy of the answers in this book and we wish to acknowledge the helpful comments provided by David Ball (Cleveland State University) in this regard It is easy for errors to creep in, however, and we will be particularly grateful to anyone who will call them to our attention Suggestions for improving the book will also be welcome Send them to: Christopher M Hadad Department of Chemistry The Ohio State University Columbus, Ohio 43210 David J Hart Department of Chemistry The Ohio State University Columbus, Ohio 43210 © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Bonding and Isomerism Chapter Summary∗ An atom consists of a nucleus surrounded by electrons arranged in orbitals The electrons in the outer shell, or the valence electrons, are involved in bonding Ionic bonds are formed by electron transfer from an electropositive atom to an electronegative atom Atoms with similar electronegativities form covalent bonds by sharing electrons A single bond is the sharing of one electron pair between two atoms A covalent bond has specific bond length and bond energy Carbon, with four valence electrons, mainly forms covalent bonds It usually forms four such bonds, and these may be with itself or with other atoms such as hydrogen, oxygen, nitrogen, chlorine, and sulfur In pure covalent bonds, electrons are shared equally, but in polar covalent bonds, the electrons are displaced toward the more electronegative element Multiple bonds consist of two or three electron pairs shared between atoms Structural (or constitutional) isomers are compounds with the same molecular formulas but different structural formulas (that is, different arrangements of the atoms in the molecule) Isomerism is especially important in organic chemistry because of the capacity of carbon atoms to be arranged in so many different ways: continuous chains, branched chains, and rings Structural formulas can be written so that every bond is shown, or in various abbreviated forms For example, the formula for n-pentane (n stands for normal) can be written as: H H H H H H C C C C C H H H H H H or CH3CH2CH2CH2CH3 or Some atoms, even in covalent compounds, carry a formal charge, defined as the number of valence electrons in the neutral atom minus the sum of the number of unshared electrons and half the number of shared electrons Resonance occurs when we can write two or more structures for a molecule or ion with the same arrangement of atoms but different arrangements of the electrons The correct structure of the molecule or ion is a resonance hybrid of the contributing structures, which are drawn with a double-headed arrow (↔) between them Organic chemists use a curved arrow ( ) to show the movement of an electron pair A sigma (σ) bond is formed between atoms by the overlap of two atomic orbitals along the line that connects the atoms Carbon uses sp3-hybridized orbitals to form four such bonds These bonds are directed from the carbon nucleus toward the corners of a tetrahedron In methane, for example, the carbon is at the center and the four hydrogens are at the corners of a regular tetrahedron with H–C–H bond angles of 109.5° ∗ In the chapter summaries, terms whose meanings you should know appear in boldface type © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Chapter Carbon compounds can be classified according to their molecular framework as acyclic (not cyclic), carbocyclic (containing rings of carbon atoms), or heterocyclic (containing at least one ring atom that is not carbon) They may also be classified according to functional group (Table 1.6) Learning Objectives∗ Know the meaning of: nucleus, electrons, protons, neutrons, atomic number, atomic weight, shells, orbitals, valence electrons, valence, kernel Know the meaning of: electropositive, electronegative, ionic and covalent bonds, radical, catenation, polar covalent bond, single and multiple bonds, nonbonding or unshared electron pair, bond length, bond energy Know the meaning of: molecular formula, structural formula, structural (or constitutional) isomers, continuous and branched chain, formal charge, resonance, contributing structures, sigma (σ) bond, sp3-hybrid orbitals, tetrahedral carbon Know the meaning of: acyclic, carbocyclic, heterocyclic, functional group Given a periodic table, determine the number of valence electrons of an element and write its electron-dot formula Know the meaning of the following symbols: δ+ δ– Given two elements and a periodic table, tell which element is more electropositive or electronegative Given the formula of a compound and a periodic table, classify the compound as ionic or covalent Given an abbreviated structural formula of a compound, write its electron-dot formula 10 Given a covalent bond, tell whether it is polar If it is, predict the direction of bond polarity from the electronegativities of the atoms 11 Given a molecular formula, draw the structural formulas for all possible structural isomers 12 Given a structural formula abbreviated on one line of type, write the complete structure and clearly show the arrangement of atoms in the molecule 13 Given a line formula, such as (pentane), write the complete structure and clearly show the arrangement of atoms in the molecule Tell how many hydrogens are attached to each carbon, what the molecular formula is, and what the functional groups are 14 Given a simple molecular formula, draw the electron-dot formula and determine whether each atom in the structure carries a formal charge ∗ Although the objectives are often worded in the form of imperatives (i.e., determine …,write …, draw …), these verbs are all to be preceded by the phrase “be able to …” This phrase has been omitted to avoid repetition © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 398 57 What is the major product of the following reaction? NH2 + N2 HONO KCN H + , 0°C Cu2(CN)2 CN CO2H N O NO2 58 NHN O What is the major product of the following reaction? H+ CH2OH O O CH2 CH2 O H3C C CH3CO2H O H3C + C CO2H CH2 C O CH3 O CH3 C CH2 O C CH2 O © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 59 399 What is the major product of the following reaction? – O CH3CH2 O OCH2CH3 + O CCH2CH3 O OH H2O, H O CH3CH2C C + CH3CH2O Na CH3CH2OH CH3CH2C O O O CH2CH2 COCH2CH3 O CH3CH2CHCHCOCH2CH3 CH3CH2CCHCCH2CH3 CH3 CH3 O O CH3CH2CCHCOCH2CH3 CH3 60 Which of the following compounds is a secondary amine? H3C CH CH3 CH3CH2NHCH3 O H3C NH2 C N CH3 NH2 61 H2NCH2CH2NH2 (CH3)3N The resonance contributor that is most important in the intermediate anion formed upon reaction of 4-chloropyridine with sodium methoxide is: Cl OCH3 Cl OCH3 Cl OCH3 – – N N – N Cl OCH3 Cl OCH3 – N 62 – N What is an IUPAC name for BrCH2CH2CH2CH=O? γ-bromobutyraldehyde 1-bromo-4-butanal 4-bromobutanal 1-bromo-3-carbonylpropane 4-bromo-1-butanone © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 400 63 What is the product of the following reaction? O NH2 + H3C C O O C CH3 O O NHCO CH3 NHC CH3 O N(CH3)2 NHOC CH3 O H3C 64 C NH2 Which reaction is most appropriate for the preparation of (CH3)2CHCH2CH2CO2H? 1 Mg ( CH3)2CHCH2 Br CO2 H3O + Ag( NH3)2+ ( CH3)2CHCH2CH O KCN ( CH3)2CHCH2CH2 Br H3O + O ( CH3)2 CHMgBr H2C CH2 Na ( CH3)2CHBr 65 + Br CH2CH2CO2H Arrange the following compounds in order of decreasing acidity: a Br CH2CH2CO2H b CH3CHCOOH c Br a>b>c b>a>c c>b>a b>c>a CH3CHCOOH F c>a>b © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 66 401 Which structure corresponds to cis-3-pentenoic acid? O OH O OH O OH OH O O OH 67 What is(are) the product(s) of the following reaction? CH3CH2CH ( OCH2CH3)2 a H2O H+ b CH3CH2OH O CH3CH2COH c d OH CH3CH2CH O CH3CH2CO CH2CH3 OH 68 a and b only c a and d b and d a and c oxiranes Cyclic ethers with a three-membered ring O C C are called: 69 epoxy resins lactams lactones alkoxides The appearance of a silver mirror in a Tollens’ test indicates the presence of: a monosaccharide cellulose an aldehyde glucose starch © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 402 70 The name benzyl α-bromopropionate refers to: O O OCCH CH3 CH2COCHCH3 Br Br O O CH2OC CH2CH2Br CHCO CH2CH2CH3 Br O CH2OCCHCH3 Br 71 Compound X gives the following test results: X Ag( NH3)2+ + no silver mirror O2N X X + H2NNH NO2 CH3O – Na + orange solid exchanges four hydrogens for deuterium CH3OD Which of the following compounds is a possible structure for X? O O CH3CO C ( CH3)3 CH3CH2CH2CCH2CH3 O O CHCH2CH2CH O CH3CCH2 O C 72 Which statements regarding the following structure are true? CH2OH O H OH H HO H H a b It is a hemiacetal It is an acetal b and d b and c OH c d O CH3 a and d b, c, and d It can be hydrolyzed by H3O+ It gives a positive Tollens’ test only b © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 73 The monosaccharide obtained from the hydrolysis of starch is: 74 D-ribose D-glucose 2-deoxy-D-ribose D-ribose, phosphoric acid, and four heterocyclic bases nucleosides nucleotides glucose and fructose 2-deoxy-D-ribose, phosphoric acid, and four heterocyclic bases constituent of urine purine potent carcinogen pyrimidine heterocyclic base present in DNA The primary structure of a protein refers to: 77 Uracil is a: 76 maltose D-galactose The products of the complete hydrolysis of DNA are: 75 403 the amino acid sequence in the polypeptide chain the presence or absence of an α helix the orientation of the amino acid side chains in space interchain cross-links with disulfide bonds whether the protein is fibrous or globular Which of the following compounds is a fat? O CH3( CH2)16 CO ( CH2)15CH3 O H2C O C ( CH2)14CH3 O H2C O HC O C O C ( CH2)14CH3 O ( CH2)14CH3 HC O H2C C C ( CH2)14CH3 O ( CH2)14CH3 H2C C ( CH2)14CH3 HO © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 404 78 Which of the following structures is a zwitterion? O – O OC CH2CH2CO – Ca 2+ O – CH3( CH2)16CO Na O + R 80 R – – C O Which of the following compounds would show only a single peak in a proton NMR spectrum? a d (CH3)4Si CH3CH2OCH2CH3 b CCl4 c CH2Cl2 only b b and c a and c a, b, and c only d Which of the following spectroscopic techniques is used to determine molecular weight? 81 O C O 79 O + – H3NCH2CO proton NMR infrared spectroscopy mass spectrometry 13 C NMR ultraviolet-visible spectroscopy The following compound can best be prepared from: OH CN O + + H2O + NaCN HCN CN CONH2 CH O + HCN Br + NaCN © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 82 405 Which of the following terms can be used to describe this pair of compounds? ClCH2 C C H3C 83 ClCH2 and CH2Cl a c e enantiomers constitutional isomers chiral a, b, and d a, d, and e C H3C b d f C CH2Cl CH3 diastereomers stereoisomers achiral a, c, and e b, d, and f b, d, and e Which of the following best describes C6H9Br3? 84 CH3 no rings, no double bonds two double bonds one ring and one double bond one ring, no double bonds one triple bond two rings The polymer segment shown below H Cl Cl H H Cl Cl H H Cl is: 85 amorphous glassy atactic isotactic Teflon Which of the following is a step-growth polymer? 86 syndiotactic block polystyrene polyvinyl nylon synthetic rubber How many stereogenic centers are present in cortisone? O CH3 O CH2OH OH CH3 cortisone O 87 3 4 The following Fischer projections CHO H OH H and H3C CH3 CHO OH represent: the same compound diastereomers rotamers enantiomers meso forms © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 406 88 The parent heterocycle present in vitamin B6 is: R HO CH2OH vitamin B6 H3C 89 pyrrole imidazole pyrimidine Oxidation of ethanol can give: 90 pyridine purine N CH2=O CO2 + H2 CH3OCH3 + CH3CO2H HOCH2CH2OH and CH3CH(OH)2 CH3CHO + CH3CO2H The structure of purine is: N N N N H The least basic nitrogen present is: 91 N-1 N-9 N-3 N-7 They all are approximately equally basic The formulas for the amino acids glycine and alanine are as follows: – – CH2CO2 CH3CHCO2 NH3 + NH3 + glycine alanine The correct formula for alanylglycine is: O + H3NCHCNH2CH2CO2– + CH3 O + H3NCHCCHCO2– H3C NH3 + O + H3NCH2CNHCHCO2– CH3 O + H3NCHCNHCH2CO2– CH3 O + H3NCHCONHCH2CO2– CH3 © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 92 93 407 Which of the following can act as a nucleophile? a H2O a, b, and d only d – b OH H+ c – d CN a and b b and d Na+ e c and e Penicillin is a β-lactam Its formula is: O R C NH R S N O O C S CH3 N CH3 CO2H O HO2C S N NH CH3 CH3 CO2H O CH3 S N CH3 CO2H R C NH CH3 CH3 O O R C NH S N 94 CH3 CH3 CO2H The antihistamine diphenhydramine (Benadryl) has the formula: CHOCH2CH2N ( CH3)2 On heating with aqueous acid, it gives: CHOH + HOCH2CH2N ( CH3)2 2 CHOH + CH3CH2N ( CH3)2 CH2 + HOCH2CH2N ( CH3)2 CHOCH2CH2NH + H3C CH3 + CHOCH2CH2N( CH3)3 © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 408 95 How many peaks appear in the 1H NMR spectrum of the following compound? CH3 H3C 96 3 How many peaks appear in the proton-decoupled C NMR spectrum of the compound in Question 95? 2 3 The 1H NMR spectrum of one isomer of C3H3Cl5 consists of a triplet at δ 4.5 and a doublet at δ 6.0, with relative areas 1:2 The structure of the isomer is: 98 13 97 CH3 CH2ClCHClCCl3 CHCl2CHClCHCl2 CH2ClCCl2CHCl2 CH3CCl2CCl3 CHCl2CH2CCl3 Cocaine is an alkaloid Its correct structure is: H2C CH CH2 HO OH OH CH 3N CO2CH3 H O C H OCH2CO2H C6 H5 O Cl O Cl Cl O Cl Cl Cl CH3 O HO 99 Which of the following statements is not true? Natural rubber is a hydrocarbon Natural rubber is made of isoprene units Natural rubber is a polymer of 1,3-butadiene Natural rubber has cis double bonds Natural rubber can be vulcanized © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 100 409 What is(are) the product(s) of the following reaction? CH3N C O + OH O CH3NH C OCH3 O + CO2 C O a polyurethane + OH CH3N 101 NHCH3 HN C O Which structure is consistent with the following 1H NMR spectrum? Relative Areas = 1:3 δ 2.0 O (CH3)3CO C C O (CH3)3CO CH3 O (CH3)3C δ 1.0 OCH3 C OCH3 O H3C C OCH3 O H3C C CH3 © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 410 102 The infrared spectrum of a compound shows absorptions at 1700 cm–1 and 3600 cm– A possible structure is: CHO CHO CHO OCH3 NH2 CHO CO2H OH 103 The parent ion in the mass spectrum of 2-propanone has the following structure: CH3 C O CH3 CH3 C O CH3 104 + O + C O CH3 CH3 – C O CH3 CH3 C + – CH3 + CH2 The major product of the following reaction is: CH3CH2COCl O O O O C AlCl O C CH2CH3 CH2CH3 O O C O CH2CH3 O C O OCH2CH3 + O – AlCl © 2012 Cengage Learning All Rights Reserved May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part Copyright 2013 Cengage Learning All Rights Reserved May not be copied, scanned, or duplicated, in whole or in part Sample Multiple Choice Questions 105 Which reaction sequence can be used to accomplish the following transformation? 106 411 O O CO2CH3 CH2OH (a) LiAlH4 (b) CH3OH, H+ (c) H2O, H+ (a) CH3OH, H+ (b) H2O, H+ (c) LiAlH4 (a) CH3OH, H+ (b) LiAlH4 (c) H2O, H+ (a) CH3OH, H+ (b) PCC (c) H2O, H+ (a) NaBH4 (b) LiAlH4 (c) PCC Arrange the following compounds in order of increasing electrophilic aromatic substitution rates b a c N N H 107 a