Organic Chemistry for Majors Final Exam - 2476 Verified Questions by Quizplus

Organic Chemistry for Majors

Final Exam

Course Introduction

Organic Chemistry for Majors is a comprehensive course designed to provide in-depth knowledge of the structure, properties, synthesis, and reactions of organic compounds. Emphasizing fundamental principles such as bonding, stereochemistry, reaction mechanisms, and functional group transformations, the course prepares students for advanced studies in chemistry, biochemistry, and related fields. Laboratory sessions complement theoretical concepts, offering students hands-on experience in organic synthesis, purification, and analysis techniques. Through problem-solving and critical thinking exercises, students develop a strong foundation essential for pursuing careers in chemistry, medicine, and the life sciences.

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Organic Chemistry 7th Edition by William H. Brown

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29 Chapters

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Chapter 1: Covalent Bonding and Shapes of Molecules

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Sample Questions

Q1) Which of the following compounds is a carboxylic acid?

A)CH3CH2COOH

B)CH3CH2OCH3

C)CH3CH2CH2OH

D)CH3CH2CHO

Answer: A

Q2) What is the approximate value of the H-C-H bond angles in methane, CH4?

A)90\(\circ\)

B)109\(\circ\)

C)120\(\circ\)

D)180\(\circ\)

Answer: B

Q3) What is the approximate C-C-C bond angle in propyne, HC\(\equiv\)CCH3?

A)90\(\circ\)

B)109\(\circ\)

C)120\(\circ\)

D)180\(\circ\)

Answer: D

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Chapter 2: Alkanes and Cycloalkanes

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Q1) How many moles of molecular oxygen (O2) are consumed in the complete combustion of one mole of octane (C8H18)?

A)12.5

B)13

C)17

D)26

Answer: A

Q2) What is the name of the linear hydrocarbon with the molecular formula C11H24?

A)heptane

B)decane

C)undecane

D)eicosane

Answer: C

Q3) How many hydrogen atoms are there in octane?

Answer: 18

Q4) Conformation B is represented by Roman numeral ____.

Answer: III

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Chapter 3: Stereoisomerism and Chirality

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Q1) Which of the following statements is not true regarding pairs of enantiomers?

A)They have identical melting points

B)They have identical boiling points.

C)They rotate plane polarized light in opposite directions

D)They react at identical rates with chiral reagents

Answer: D

Q2) Which of the following substituents has the highest priority according to the Cahn-Ingold-Prelog system used in assigning R and S configurations?

A)"-NH2"

B)"-NHCH3"

C)"-CH2NH2"

D)"-CH2NHCH3"

Answer: B

Q3) Which of the following is the definition of a meso compound?

A)A molecule with stereocenter centers which is chiral

B)A molecule with stereocenter centers which is not chiral

C)A diastereomer with no stereocenter centers

D)A chiral compound with more than one stereocenter center

Answer: B

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Chapter 4: Acids and Bases

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Sample Questions

Q1) Provide a brief explanation, based on features of the molecules, for the following trend in pKa values?

CH3CH2OH > CH3COOH 15.9 4.76

Q2) Which of the following is the strongest acid?

A)CH3NH2

B)CH3PH2

C)CH3OH

D)CH3SH

Q3) Which of the following is easiest to deprotonate?

A)CH4

B)CH3CH3

C)CH2=CH2

D)HC\(\equiv\)CH

Q4) Which of the following is a feature of a Brønsted-Lowry acid?

A)proton donor

B)proton acceptor

C)electron pair donor

D)electron pair acceptor

Q5) Which acid has the smallest Ka?

Page 6

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Chapter 5: Alkenes: Bonding, Nomenclature, and Properties

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Q1) What types of units make up terpenes?

A)isoprene

B)propene

C)vitamin A

D)pentadiene

Q2) How many isomers of 1,3,5-heptatriene exist?

A)1

B)2

C)4

D)8

Q3) What is the approximate value of the C-C-C bond angle in propene?

A)90\(\circ\)

B)109\(\circ\)

C)120\(\circ\)

D)180\(\circ\)

Q4) Provide the bond-line structure of (Z)-4,5-dichloro-2-pentene.

Q5) A compound likely to be a liquid at room temperature is represented by the letter ______.

Q6) What is the value of the index of hydrogen deficiency of a molecule with the formula C8H19N?

Page 7

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Chapter 6: Reactions of Alkenes

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Q1) Which of the following concepts explains why tertiary carbocations are more stable than primary and secondary carbocations?

A)electronegativity

B)resonance

C)hyperconjugation

D)the octet rule

Q2) Product _____ would have a higher energy transition state for the formation of the intermediate leading to it.

Q3) Product _____would be formed via a primary carbocation.

Q4) Product _____ would have the lowest activation energy required to form the intermediate in the mechanism.

Q5) Which of the following reactions of alkenes is not stereospecific?

A)bromination (treatment with Br2 in CHCl3)

B)hydrogenation (treatment with H2/Pt)

C)acid-catalyzed hydration (treatment with aqueous H2SO4)

D)bromohydrin formation (treatment with Br2/H2O)

Q6) Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization.

Q7) Product _____would be the major product.

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Chapter 7: Alkynes

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Sample Questions

Q1) What type of intermediate is formed in the Hg2+ catalyzed hydration of an alkyne??

A)an alcohol

B)an enol

C)a 1,2-diene

D)an epoxide

Q2) What is the IUPAC name of the following compound? CH3CH2CH2-C\(\equiv\)C-CH(CH3) 2

A)1-isopropyl-1-pentyne

B)2-methyl-3-heptyne

C)6-methyl-4-heptyne

D)isopropyl propyl ethyne

Q3) What is the IUPAC name of the following compound? (CH3)2CHCH2-C\(\equiv\)CH(CH3)2

A)2,6-dimethyl-3-heptyne

B)2,6-dimethyl-4-heptyne

C)1,1,5,5-tetramethyl-2-pentyne

D)4-nonyne

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Chapter 8: Haloalkanes, Halogenation, and Radical Reactions

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Sample Questions

Q1) The boiling points of alkanes increase as the length of the carbon chain increases but decrease as the amount of branching increases.

A)True

B)False

Q2) Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point)?

A)chloromethane > chloroethane > 2-chloropropane > 2-chloro-2-methylpropane

B)2-chloro-2-methylpropane > 2-chloropropane > chloroethane > chloromethane

C)chloroethane > chloromethane > 2-chloro-2-methylpropane > 2-chloropropane

D)chloromethane > 2-chloro-2-methylpropane > 2-chloropropane > chloroethane

Q3) Which of the following statements is not true?

A)Homolytic cleavage of a bond in a neutral molecule gives two radicals.

B)Radicals have one or more unpaired electrons.

C)Movement of single electrons is depicted using a "fishhook arrow".

D)The C-F bond is the weakest bond between carbon atom and a halogen.

Q4) The number of allylic positions in compound A is ______.

Q5) During bromination using NBS, the concentration of bromine remains ________throughout the course of the reaction.

Q6) The name of one of the minor products of this reaction is____________________. Page 10

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Chapter 9: Nucleophilic Substitution and Beta-Elimination

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Q1) These reactions are classified as ________________reactions.

Q2) Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium azide, NaN3?

A)1-fluorohexane

B)1-chlorohexane

C)1-bromohexane

D)1-iodohexane

Q3) The reaction of tert-butyl chloride, (CH3)3CCl, with water in an inert solvent gives tert-butyl alcohol, (CH3)3COH. What is the effect of doubling the concentration of water on the rate of the reaction?

A)the rate remains the same

B)the rate decreases by a factor of 2

C)the rate increases by a factor of 2

D)the rate increases by a factor of 4

Q4) Which of the following is not a characteristic of SN2 reactions?

A)the electrophilic carbon undergoes inversion of stereochemistry

B)the rate is proportional to the concentration of substrate

C)the rate is proportional to the concentration of nucleophile

D)the rate is independent of the solvent

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Chapter 10: Alcohols

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Sample Questions

Q1) Which of the following has the highest boiling point?

A)1-butanol

B)2-butanol

C)tert-butyl alcohol

D)1,4-butanediol

Q2) What is the approximate pKa value of ethanol?

A)-5

B)5

C)16

D)25

Q3) (CH3)3CO- Na+ would be formed by the reaction of sodium metal and 1-butanol.

A)True

B)False

Q4) What is the major organic product obtained upon heating a mixture of 2-butanol and 85% H3PO4?

A)1-butene

B)cis-2-butene

C)trans-2-butene

D)2-methylpropene (isobutylene)

Page 13

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Chapter 11: Ethers, Epoxides, and Sulfides

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Sample Questions

Q1) When cyclopentene is treated with peroxyacetic acid, the product that forms is

Q2) Which of the following statements are true?

1)ethanol is more soluble in water than dimethyl ether

2)ethanol has a higher boiling point than dimethyl ether

3)ethanol has the same molecular weight as dimethyl ether

A)only 1

B)only 1 and 2

C)only 1 and 3

D)1, 2 and 3

Q3) Which of the following reactions provides tert-butyl methyl ether in a high yield?

A)potassium tert-butoxide + iodomethane

B)sodium methoxide + tert-butyl bromide

C)methanol + tert-butyl alcohol in the presence of KOH

D)iodomethane + tert-butyl bromide in the presence of KOH

Q4) Adding Br2 in H2O will distinguish between ethyl phenyl ether and allyl phenyl ether.

A)True

B)False

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Chapter 12: Infrared Spectroscopy

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Q1) In terms of the electromagnetic spectrum, 2870 cm-1represents lower energy than 2.91 * 1016 Hz.

A)True

B)False

Q2) The area in the infrared spectrum between 1400 and 400 cm-1 is called the functional group region.

A)True

B)False

Q3) _____ C=O, C=N, and C=C bond absorptions.

A)4000 to 2500 cm-1

B)2500 to 2000 cm-1

C)2000 to 1500 cm-1

D)below 1500 cm-1

Q4) Provide a brief explanation to account for the observation that the frequency of the C=O stretching absorption in the infrared spectrum of N,N-dimethylacetamide, CH3CON(CH3)2, is higher than that of methyl acetate, CH3CO2CH3.

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

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Sample Questions

Q1) Which of the following is true for pair of enantiotopic protons?

1)They will appear at the same chemical shift in an achiral (i.e., nonchiral environment)

2)They will appear at the same chemical shifts in a chiral environment

A)only 1

B)only 2

C)neither 1 nor 2

D)both 1 and 2

Q2) Which feature in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound?

A)number of signals

B)integral

C)multiplicity

D)chemical shift

Q3) ______ 1

Q4) How many sets of equivalent protons are there in 2-methylhexane?

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Chapter 14: Mass Spectrometry

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Sample Questions

Q1) The base peak in this spectrum occurs at a m/z of ______.

Q2) What is the principle that allows us to use mass spectrometry to determine the molecular weight of a compound?

A)higher molecular weight compounds are less volatile

B)higher molecular weight compounds are more dense

C)a beam of higher molecular weight cations is deflected less by a magnetic field

D)ions with higher molecular weight absorb higher frequencies of light

Q3) Which of the following gives rise to a prominent M - 18 peak in the mass spectrum?

A)cyclohexane

B)cyclohexene

C)1-chlorocyclohexane

D)cyclohexanol

Q4) Which of the following sets of molecular ions does an alkyl chloride possess?

A)two molecular ions in a 2:1 ratio separated by two mass units

B)two molecular ions in a 1:1 ratio separated by two mass units

C)three molecular ions in a 1:2:1 ratio separated by two mass units

D)two molecular ions in a 3:1 ratio separated by two mass units

Q5) The peak at a m/z of _____ represents the base peak.

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Chapter 15: An Introduction to Organometallic Compounds

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Q1) The percent ionic character of a C-Mg bond is less than that of a C-Cu bond.

A)True

B)False

Q2) Which of the following is the best choice of solvent for the formation of phenylmagnesium bromide by the reaction of bromobenzene with magnesium?

A)water

B)methanol

C)diethyl ether

D)acetic acid

Q3) Substance ____ is the nucleophile in the reaction.

A)A

B)B

C)C

Q4) What term describes the process whereby an alkyl halide undergoes reaction with magnesium metal to give an alkylmagnesium bromide (Grignard reagent)?

A)nucleophilic substitution

B)electrophilic addition

C)oxidative addition

D)reductive elimination

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Chapter 16: Aldehydes and Ketones

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Q1) Which of the following is the best description of the overall transformation involved in a Wittig reaction?

A)addition

B)substitution

C)elimination

D)rearrangement

Q2) Which of the following statements is not true?

A)The carbon atom of a carbonyl group is electrophilic

B)In general, aldehydes are more electrophilic than ketones

C)Nucleophilic addition to carbonyl groups can be catalyzed by acid or base

D)Addition of a nucleophile to a carbonyl group changes the hybridization of the carbonyl carbon from sp3 to sp2 hybridization

Q3) The first step in the reaction mechanism is the protonation of the ________group.

Q4) Which of the following statements is not true?

A)Reaction of benzophenone with methanol in the presence of acid gives a acetal

B)Reaction of butanal with ethanol in the presence of base gives an acetal

C)Reaction of benzaldehyde with ethanol in the presence of acid gives an acetal

D)Reaction of acetone with methanol in the presence of base gives a hemiacetal

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Chapter 17: Carboxylic Acids

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Q1) The benzyl alcohol will be recovered from the _______ layer.

Q2) Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A)ICH2COOH > ClCH2COOH > FCH2COOH

B)Cl2CHCOOH > ClCH2COOH > CH3COOH

C)CH3CH2OH > FCH2COOH >

ClCH2COOH

D)CH3COOH > FCH2COOH > CH3CH2OH

Q3) Malonic acid is an example of a \(\beta\)-ketoacid.

A)True

B)False

Q4) Which of the following is a reactive intermediate in the thermal decarboxylation of a 1,3-diacid?

A)enol

B)carbocation

C)carbanion

D)carboxylate

Q5) The 2,3,4,5-tetramethylbenzene will be recovered from the _______ layer.

Q6) When CO2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, ____________ _____ is produced.

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Chapter 18: Functional Derivatives of Carboxylic Acids

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Q1) Which of the following is the correct order of decreasing leaving group ability in nucleophilic acyl substitutions (better leaving group > worse leaving group)?

A)Cl- > NH2- > CH3O- B)NH2- > CH3O- > Cl-

C)Cl-> CH3O- > NH2-

D)CH3O- > Cl- > NH2-

Q2) Which of the following best describes the key mechanistic steps in the reaction of an anhydride and an amine to form an amide?

A)addition followed by elimination

B)elimination followed by addition

C)substitution followed by addition

D)addition followed by decarboxylation

Q3) Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?

A)elimination followed by addition

B)addition followed by decarboxylation

C)addition followed by elimination

D)substitution followed by addition

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Chapter 19: Enolate Anions and Enamines

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Q1) The alkyl halide that should be used to produce octanoic acid via the malonic ester synthesis is 1-bromooctane.

A)True

B)False

Q2) A 1,6-diester will produce a five-membered ring via a Dieckmann cyclization.

A)True

B)False

Q3) How many different aldols (\(\beta\)-hydroxyaldehydes), including constitutional isomers and stereoisomers, are formed upon treatment of butanal with base?

A)1

B)2

C)3

D)4

Q4) Claisen and aldol condensations can result in cyclization but the Robinson annulation cannot.

A)True

B)False

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Page 22

Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

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Q1) The dienophile in the reaction is ____.

A)A

B)B

C)C

Q2) The kinetically controlled product in this reaction is _____.

A)A

B)B

C)C

D)D

Q3) Which of the following relationships is not valid as applied to ultraviolet-visible spectroscopy?

A)"A = log (Io/I)"

B)"A = \(\varepsilon\)cl"

C)"\(\Delta\)E = hv"

D)"A = \(\lambda\)maxl"

Q4) When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule corresponds to the amount necessary to excite electrons from one molecular orbital to another.

A)True

B)False

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Chapter 21: Benzene and the Concept of Aromaticity

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Q1) Which of the following statements is not true about the structure of benzene?

A)six atomic 2p-orbitals overlap to form six \(\pi\)-molecular orbitals

B)there are three bonding \(\pi\)-molecular orbitals and three \(\pi\)-antibonding molecular orbitals

C)the ground state electronic configuration of benzene has six electrons in three \(\pi\)-bonding molecular orbitals

D)the bonds alternate in length around the ring

Q2) The hybridization of the nitrogen atom in sulfathiazole is ______.

A. sp

B. sp2

C. sp3

Q3) What is the intermediate in the reaction of ethylbenzene with NBS in the presence of benzoyl peroxide to give 1-bromo-1-phenylethane?

A)Benzylic anion

B)Benzylic cation

C)Benzylic radical

D)Benzylic carbene

Q4) The NMR data would seem to indicate that this compound is ____________.

Q5) Using the Hückel criteria, the compound would be ______________.

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Chapter 22: Reactions of Benzene and Its Derivatives

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Q1) Which of the following is not true about Meissenheimer complexes?

A)They are resonance-stabilized anions

B)They are formed upon addition of a nucleophile to aryl halides

C)They are aromatic

D)They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanism

Q2) Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

A)treatment of benzene with isopropyl alcohol and HF

B)treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl

C)treatment of benzene with 1-chloropropane and AlCl3

D)treatment of benzene with 1-propene and HF

Q3) Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH2CN)?

A)Bimolecular nucleophilic substitution (SN2)

B)Nucleophilic aromatic substitution by elimination-addition

C)Nucleophilic aromatic substitution by addition-elimination

D)Electrophilic aromatic substitution

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Page 25

Chapter 23: Amines

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Q1) Which of the following amines can be prepared by reduction of an amide?

A)tert-butyl amine

B)2-hexanamine

C)N-methyl-1-butanamine

D)aniline

Q2) Provide a brief explanation, based on features of the molecules, for the following difference in pKa values?

CH3NH2 > NH3

10.64 9.26

Q3) Aliphatic 3o amines with three different groups on nitrogen can be resolved.

A)True

B)False

Q4) Substance _____ is pyridine.

Q5) The name of the product formed by reacting KCN and CuCN with benzenediazonium chloride is ________________________.

Q6) The ammonia ion of substance ____ will have the smallest pKa.

Q7) The name of the product formed by reacting CuCl and HCl with benzenediazonium chloride is ________________________.

Page 26

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

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Q1) In the Heck reaction, all reactants are required in stoichiometric amounts except the Pd(0) species.

A)True

B)False

Q2) ______involves the use of organoboron compounds.

A)Heck reaction

B)Stille coupling

C)Suzuki coupling

D)Sonogashira coupling

E)Alkene metathesis

Q3) The intermediate in a Heck reaction can be described as a tetrahedral Pd(II) species.

A)True

B)False

Q4) ______involves the use of stannates.

A)Heck reaction

B)Stille coupling

C)Suzuki coupling

D)Sonogashira coupling

E)Alkene metathesis

Page 27

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Chapter 25: Carbohydrates

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Q1) The number of hydroxyl groups in the pyranose form of glucose is _____.

Q2) The difference between the pyranose and furanose forms of a given aldohexose is the ring size.

A)True

B)False

Q3) The structures that represent reducing sugars are:

a. only the ketoses.

b. only the aldoses.

c. all of these structures.

Q4) A glycoside is formed upon reaction of glucopyranose with NaBH4.

A)True

B)False

Q5) Structure ____ represents a ketohexose.

Q6) The anomer of ribose is drawn is _______. (alpha or beta)

Q7) Starch, cellulose, and surcrose are all classified as polysaccharides.

A)True

B)False

Q8) Structure ____ represents a aldopentose.

Q10) The enantiomer of ribose is drawn is _______. (D or L) Page 28

Q9) The correct name for the cyclic structure is__________________________.

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Chapter 26: Lipids

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Q1) Which of the following is not found in a fluid mosaic lipid bilayer?

A)phospholipid

B)cholesterol

C)protein

D)nucleic acid

Q2) What are the roles of LDL and HDL? Which one is "good" cholesterol, which one is bad"?

Q3) The main difference between fats and oils is that oils contain a lower percentage of unsaturated alkyl chains.

A)True

B)False

Q4) Which of the following is not an eicosanoid?

A)prostaglandin E2

B)leukotriene C4

C)thromboxane A2

D)cholesterol

Q5) Explain the formation of "soap scum", formed in areas which have "hard" water. What chemical reaction takes place, and what physical process results?

Q6) Male sex hormones like testosterone are called _____________.

Page 30

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Chapter 27: Amino Acids and Proteins

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Sample Questions

Q1) Which of the following is not a polypeptide?

A)L-HIV-1 protease

B)hemoglobin

C)myoglobin

D)glycogen

Q2) Consider the following octapeptide.

Ala-Val-Trp-Lys-Phe-Gly-Arg-Met

The fragments that would be obtained by a trypsin hydrolysis are Ala-Val-Trp-Lys and Phe-Gly-Arg and Met.

A)True

B)False

Q3) To what structural feature does the term "quaternary structure" refer?

A)the sequence of amino acids in proteins

B)the overall folding pattern of proteins

C)the aggregation of polypeptides

D)the conformation of local regions of polypeptides

Q4) In terms of the number of amino acid residues Cys-Ile-Ser-Asp-Gly-His-Gly-Gly would be classified as a(n) ________________.

Q5) Hydrogen bonds, \(\alpha\)-helices, and pleated sheets are properties of structure of proteins.

Page 31

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Chapter 28: Nucleic Acids

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Sample Questions

Q1) What sequence is fully complementary to the following sequence? 5'-GTACGACT-3'

A)5'-GTACGACT-3'

B)5'-TCAGCATG-3'

C)5'-AGTCGTAC-3"

D)5'-CATGCTGA-3'

Q2) A double-stranded DNA molecule that contains 22%, on a mole basis, T must also contain ___% G.

Q3) Which of the following is a complimentary pair of hydrogen-bonded bases found in RNA?

A)A - C

B)A - G

C)A - T

D)A - U

Q4) Relative to the secondary structure of DNA, there is no restriction on the sequence of bases along a polynucleotide chain. The exact sequence carries the genetic information.

A)True

B)False

Q5) Provide the structure of 2-deoxyribose.

Q6) A three base sequence called a "codon" codes for one _______________.

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Chapter 29: Organic Polymer Chemistry

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Sample Questions

Q1) Which type of polymerization is initiated by a mixture of naphthalene and sodium metal?

A)anionic

B)cationic

C)radical

D)Ziegler-Natta

Q2) High degrees of crystallinity are associated with polymers with weak intermolecular forces.

A)True

B)False

Q3) Provide the structure of poly(ethylene succinate).

Q4) What type of intermediate is formed in the polymerization of styrene with butyllithium?

A)carbocation

B)carbanion

C)radical

D)radical anion

Q5) This polymer would be classified as a poly______.

Q6) Provide the structure of polystyrene.

Q7) Provide the structure of poly(butylene adipamide).

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