General Chemistry II Exam Materials - 2476 Verified Questions

General Chemistry II

Exam Materials

Course Introduction

General Chemistry II builds upon the foundational concepts introduced in the first semester, delving deeper into the principles of chemistry that govern matter and its interactions. Topics typically include chemical kinetics, chemical equilibrium, acid-base chemistry, thermodynamics, electrochemistry, and an introduction to coordination compounds. The course emphasizes problem-solving skills, laboratory techniques, and the application of theoretical concepts to real-world chemical systems, preparing students for more advanced studies in chemistry and related fields.

Recommended Textbook Organic Chemistry 7th Edition by William H. Brown

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Chapter 1: Covalent Bonding and Shapes of Molecules

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Q1) Which of the following statements is not true about the acetate anion, CH₃CO₂^-?

A)The oxygen atoms bear the same amount of charge

B)The two carbon-oxygen bonds are the same length

C)The carbon atom bears the negative charge

D)It is basic

Answer: C

Q2) What is the approximate strength of the C-C bond of ethane?

A)376 kJ/mol (90 kcal./mol)

B)422 kJ/mol (101 kcal./mol)

C)556 kJ/mol (133 kcal./mol)

D)727 kJ/mol (174 kcal./mol)

Answer: A

Q3) Which atomic orbitals overlap to form the carbon-carbon \(\sigma\) molecular bonding orbital of ethyne, HC\(\equiv\)CH?

A)C2p + C2p

B)C2sp + C2sp

C)C2sp² + C2sp²

D)C2sp³ + C2sp³

Answer: B

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Chapter 2: Alkanes and Cycloalkanes

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Sample Questions

Q1) There are four constitutional isomers for the molecular formula C₆H₁₄.

A)True

B)False

Answer: False

Q2) Provide a line-bond structure of hexanoic acid.

Answer: 11ea7d75_f5df_2928_b9bd_152ea302b1fb_TB1813_00_TB1813_00

Q3) Which of the following statements is not true?

A)Combustion of an alkane is an exothermic reaction.

B)The heat of combustion of propane is three times that of methane.

C)The constitutional isomers of C₇H₁₆ have different heats of combustion from one another

D)The products of combustion of an alkane are H₂O and CO₂. Answer: B

Q4) The most stable conformation of an alkane occurs when carbon-carbon bonds are staggered and bulky groups are anti.

A)True

B)False

Answer: True

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Chapter 3: Stereoisomerism and Chirality

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Q1) ______________ are stereoisomers that are not mirror images.

Answer: Diastereomers diastereomers

Q2) A pure sample of the R enantiomer of a compound has a specific rotation, [\(\alpha\)], of +20^\(\circ\). A solution containing 0.2 g/mL of a mixture of enantiomers rotates plane polarized light by -2^\(\circ\) in a 1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture?

A)25% R

B)40% S

C)50% S

D)70% R

Answer: C

Q3) 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

Q4) A mixture containing 0.50 mmol of each enantiomer is called a ___________mixture.

Answer: racemic

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Chapter 4: Acids and Bases

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Sample Questions

Q1) Which of the following is a feature of a Lewis acid?

A)proton donor

B)proton acceptor

C)electron pair donor

D)electron pair acceptor

Q2) Which of the following is the strongest acid?

A)CH₃CH₃

B)CH₃NH₂

C)CH₃OH

D)CH₃F

Q3) Which of the following is present in the highest concentration upon dissolution of acetic acid in water?

A)OH^-

B)H₃O⁺

C)CH₃COOH

D)CH₃COOH⁺

Q4) Provide the equation that relates the acid dissociation constant, K_a, to the pK_a of an acid.

Q5) Which acid has the smallest K_a?

Q6) Which acid has the strongest conjugate base?

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Chapter 5: Alkenes: Bonding, Nomenclature, and Properties

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Q1) What is the approximate value of the H-C-H bonds angle in ethene?

A)90^\(\circ\)

B)109^\(\circ\)

C)120^\(\circ\)

D)180^\(\circ\)

Q2) Provide the bond-line structure of (2E,5E)-2,5-octadiene.

Q3) What is the index of hydrogen deficiency of a compound with a molecular formula of C₆H₈?

A)0

B)1

C)2

D)3

Q4) 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^\(\circ\)

Q5) What is the value of the index of hydrogen deficiency of a molecule with the formula C₈H₁₂?

Page 7

Q6) Provide the bond-line structure of (2Z,6E)-octa-2,6-diene.

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Chapter 6: Reactions of Alkenes

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Q1) What is the major product obtained upon addition of Br₂ to (R)-4-tert-butylcyclohexene?

A)(1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane

B)(1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane

C)(1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane

D)(1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane

Q2) 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

Q3) Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization.

Q4) Product _____would be the major product.

Q5) Markovnikov addition of HCl to propene involves the formation of a secondary carbocation.

A)True

B)False

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Chapter 7: Alkynes

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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? (CH₃)₂CHCH₂-C\(\equiv\)CH(CH₃)< sub>2</sub>

A)2,6-dimethyl-3-heptyne

B)2,6-dimethyl-4-heptyne

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

D)4-nonyne

Q3) Consider an unknown with the molecular formula C₄H₆. The index of hydrogen deficiency of this compound is _____.

Q4) Approximately how long is a carbon-carbon triple bond of an alkyne?

A)110 pm

B)121 pm

C)135 pm

D)156 pm

Page 9

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Chapter 8: Haloalkanes, Halogenation, and Radical Reactions

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Q1) The number of possible dibromination products of 2-methylpropane is______.

Q2) What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH₃) and bromine?

A)benzylic carbocation

B)benzylic carbanion

C)benzylic radical

D)cyclic bromonium ion

Q3) What is the geometry of the central carbon atom of a tert-butyl radical?

A)tetrahedral

B)trigonal planar

C)trigonal pyramidal

D)square planar

Q4) How many \(\pi\)-bonding, non-bonding, and antibonding orbitals does the allyl radical possess?

A)one bonding, one nonbonding, and one antibonding

B)two bonding, no nonbonding, and no antibonding

C)two bonding, one nonbonding, and no antibonding

D)three bonding, no nonbonding, and no antibonding

Page 10

Q5) The number of possible monobromination products of cyclopentane is______.

Q6) The number of allylic positions in compound A is ______.

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Chapter 9: Nucleophilic Substitution and Beta-Elimination

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Sample Questions

Q1) Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?

A)water

B)N,N-dimethylformamide

C)hexane

D)toluene, PhCH₃

Q2) What is the major product formed upon treatment of (R) 1-bromo-4-methylhexane with sodium cyanide?

A)(R) 1-cyano-4-methylhexane

B)(S) 1-cyano-4-methylhexane

C)(R) 4-methyl-1-hexene

D)(S) 4-methyl-1-hexene

Q3) Which of the following sets consists of only polar aprotic solvents?

A)water, hexane, methanol

B)acetic acid, DMF, toluene

C)DMSO, ethanol, acetonitrile

D)DMF, acetonitrile, DMSO

Q4) These reactions are classified as ________________reactions.

Q5) Compound C is formed by an _____ mechanism.

Q6) The mechanism for these reactions is _______.

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Chapter 10: Alcohols

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Q1) Including stereoisomers, the number alkene isomers produced by the acid-catalyzed dehydration of 3-methyl-3-hexanol is _____.

Q2) Provide the complete IUPAC name for the starting material in this reaction.

Q3) What type of reactive intermediate is formed in the reaction of tert-butyl alcohol with H₂SO₄ to give methylpropene?

A)tert-butyl cation

B)tert-butyl anion

C)tert-butyl radical

D)tert-butoxide

Q4) Which of the following has the highest boiling point?

A)pentane

B)methyl propyl ether

C)diethyl ether

D)1-butanol

Q5) (CH₃)₃COH would react faster than (CH₃)₂CHCH₂OH under S_N1 conditions.

A)True

B)False

Q6) _______Oxidation of a primary alcohol to a carboxylic acid.

Page 13

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Chapter 11: Ethers, Epoxides, and Sulfides

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Q1) What type of reactive intermediate is formed in the reaction of tert-butyl methyl ether with HBr to give tert-butyl bromide?

A)tert-butyl anion

B)tert-butoxide

C)tert-butyl radical

D)tert-butyl cation

Q2) Which of the following reactions provides anisole (PhOCH₃) in a high yield?

A)phenol + sodium methoxide

B)bromobenzene + bromomethane

C)sodium phenoxide (PhONa) + bromomethane

D)bromobenzene + sodium methoxide

Q3) The synthesis of dipropyl ether can be accomplished by reacting 1-propanol with H₂SO₄ at 140°C.

A)True

B)False

Q4) The name of the product of the reaction is _______________________.

Q5) The reaction shown here is an example of a ______________ ________synthesis

Q6) The reaction shown here proceeds by a(n) _______ mechanism.

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Chapter 12: Infrared Spectroscopy

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Q1) _____ triple bond stretching vibrations.

A)4000 to 2500 cm^-¹

B)2500 to 2000 cm^-¹

C)2000 to 1500 cm^-¹

D)below 1500 cm^-¹

Q2) An IR spectrum of an unknown organic molecule having the formula which contains carbon, hydrogen, and oxygen reveals a strong absorption at 1715-1725 cm^-1. This molecule is most likely an ether.

A)True

B)False

Q3) Which of the following bonds undergoes stretching at the highest frequency?

A)C=O

B)C-O

C)C=C

D)C-C

Q4) _____ 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

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Chapter 13: Nuclear Magnetic Resonance Spectroscopy

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Q1) How many signals appear in the proton-decoupled ¹³C NMR spectrum of 4-bromotoluene?

A)3

B)4

C)5

D)7

Q2) The splitting of signals in the ¹H NMR spectrum provides information about the number of neighboring protons of each proton in the compound.

A)True

B)False

Q3) Which of the following combinations of peaks appears in the ¹H NMR spectrum of 2,3-dimethylbutane?

A)two doublets

B)a doublet and a septet

C)a singlet and two doublets

D)a doublet and an octet

Q4) _____The number of nonequivalent hydrogen atoms in this compound.

Q5) ______ 1

Q6) ______ 1

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Chapter 14: Mass Spectrometry

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Q1) Which of the following gives rise to a prominent peak in the mass spectrum with m/z of M - 31?

A)2-methylhexanoic acid

B)methyl hexanoate

C)ethyl hexanoate

D)hexanoic acid

Q2) Which of the following gives rise to a prominent peak in the mass spectrum at m/z of 39?

A)1-octyne

B)4-octyne

C)5-methyl-3-octyne

D)2,2-dimethyl-3-heptyne

Q3) Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 41?

A)1-hexene

B)2-hexyne

C)3-hexanol

D)2-chlorohexane

Q4) The base peak in this spectrum occurs at a m/z of ______.

Q5) The peak at a m/z of _____ represents M⁺.

Page 17

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Chapter 15: An Introduction to Organometallic Compounds

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Q1) Substance ____ is the nucleophile in the reaction.

A)A

B)B

C)C

Q2) Which of the following bonds has the most ionic character?

A)C-Sn

B)C-Cu

C)C-Zn

D)C-Li

Q3) In the formation of the ether soluble complex in a Grignard reaction, magnesium acts as a Lewis base and the ether as a Lewis acid.

A)True

B)False

Q4) The percent ionic character of a C-Mg bond is less than that of a C-Cu bond.

A)True

B)False

Q5) Substance A is formed from the reaction of Mg with ______________.

Q6) The reaction intermediate formed by the reaction of KOH with the alkene is called_____________.

Q7) Substance A is termed a ___________reagent.

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Chapter 16: Aldehydes and Ketones

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Q1) Which of the following statements is not true?

A)The reaction of a ketone with methanol in the presence of acid to give a acetal proceeds via a resonance stabilized cation

B)Protonation of a ketone increases its electrophilicity

C)The conversion of a hemiacetal to an acetal under acidic conditions proceeds via an S_N1 mechanism

D)The conversion of a hemiacetal to an acetal is catalyzed by both acid and base

Q2) What type of reaction takes place upon treatment of a ketone with HCN to form a cyanohydrin?

A)nucleophilic addition

B)electrophilic addition

C)nucleophilic substitution

D)electrophilic substitution

Q3) Which of the following is a reactive intermediate in the reaction of acetone with bromine in acetic acid to form 1-bromo-2-propanone?

A)carbanion

B)enol

C)enolate

D)radical

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Chapter 17: Carboxylic Acids

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Q1) In order to recover the 2-hydroxybenzoic acid, a strong ______ must be added to the appropriate layer.

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

A)FCH₂COOH > CH₃COOH > F₂CHCOOH

B)FCH₂COOH > CH₃COOH > CH₃OH

C)CH₃CH₂OH > ClCH₂COOH > BrCH₂COOH

D)CH₃COOH > ClCH₂COOH > CH₃OH

Q3) Ethyl propanoate (CH₃CH₂COOCH₂CH₃) can be prepared by the reaction of ethanol with ____________ acid.

Q4) The 2,3,4,5-tetramethylbenzene will be recovered from the _______ layer.

Q5) Which of the following is the most soluble in water?

A)acetic acid

B)pentanol

C)butanoic acid

D)pentanal

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

Page 20

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Chapter 18: Functional Derivatives of Carboxylic Acids

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Q1) The substance that is the most reactive toward nucleophilic acyl substitution is

Q2) Both amides and nitriles are acyl derivatives of carboxylic acids.

A)True

B)False

Q3) Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)?

A)esters > amides > acid chlorides

B)amides > acid chlorides > esters

C)acid chlorides > esters > amides

D)esters > acid chlorides > amides

Q4) 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

Q5) The substance that is classified as an anhydride is _____.

Q6) An anhydride is represented by the structure numbered ____.

Page 21

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Chapter 19: Enolate Anions and Enamines

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Q1) 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

Q2) Which of the following are intermediates in the acid catalyzed aldol reaction of propanal to form 2-methyl-2-pentenal?

1)enol

2)enolate

3)tetrahedral carbonyl intermediate

4)aldol

A)only 1 and 2

B)only 1, 3 and 4

C)only 2, 3 and 4

D)1, 2, 3 and 4

Q3) Tautomerization is catalyzed by both acids and bases.

A)True

B)False

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Chapter 20: Dienes, Conjugated Systems, and Pericyclic Reactions

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Q1) What are the units of absorbance, A, in ultraviolet-visible spectroscopy?

A)J.mol^-¹

B)nm.mol^-¹

C)J.mol^-¹.M^-¹

D)none, A is a dimensionless quantity

Q2) Which of the following electronic transitions is apparent in the ultraviolet-visible spectrum of 1,3-butadiene?

A)"n \(\rarr\) \(\pi\)*"

B)"\(\pi\) \(\rarr\) \(\pi\) *"

C)" \(\sigma\)\(\rarr\) \(\pi\) *"

D)" \(\sigma\) \(\rarr\) \(\pi\)"

Q3) Which of the following terms describes the mechanism for the addition of Br₂ to butadiene?

A)electrophilic addition

B)nucleophilic addition

C)pericyclic addition

D)conjugate addition

Q4) Draw two resonance structures of the reactive intermediate that accounts for the formation of 1,2- and 1,4-addition products upon reaction of 1,3-butadiene with one equivalent of HBr.

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Chapter 21: Benzene and the Concept of Aromaticity

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Q1) This structure contains ____ \(\pi\) electrons.

Q2) If named as an annulene, the name would be [ __ ] annulene.

Q3) How many p orbital electrons are present in cyclopentadienyl anion?

A)4

B)6

C)7

D)8

Q4) How many p orbital electrons are present in furan?

A)4

B)6

C)7

D)8

Q5) What is the hybridization of the oxygen atom of furan?

A)s

B)sp

C)sp²

D)sp³

Q6) The NMR data would seem to indicate that this compound is ____________.

Q7) According to Hückel criteria, sulfathiazole is predicted to be ___________.

Q8) List all of the requirements of a molecule for it to be considered aromatic.

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Chapter 22: Reactions of Benzene and Its Derivatives

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Q1) What is the electrophile in the reaction of benzene with tert-butyl chloride and AlCl₃?

A)CH₃⁺

B)Cl⁺

C)(CH₃)C⁺

D)benzene

Q2) What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

A)Meisenheimer complex

B)benzyne

C)cyclohexadienyl cation

D)benzyl radical

Q3) What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl₃ to give 4-chloro-1-tert-butylbenzene?

A)Meisenheimer complex

B)benzyne

C)cyclohexadienyl cation

D)benzyl radical

Q4) The name of product D is ________________________.

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Chapter 23: Amines

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Q1) Which of the following amines can be prepared from an organic bromide by reaction with sodium azide followed by reduction?

A)aniline

B)benzylamine

C)N-ethyl-2-butanamine

D)tert-butyl amine

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

CH₃NH₂ > NH₃ 10.64 9.26

Q3) The name of the product formed by reacting KCN and CuCN with benzenediazonium chloride is ________________________.

Q4) Which of the following is the strongest base?

A)ammonia

B)dimethylamine

C)aniline

D)4-nitroaniline

Q5) The ammonia ion of substance ____ will have the smallest pK_a.

Q6) Substance _____ is pyridine.

Page 26

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Chapter 24: Catalytic Carbon-Carbon Bond Formation

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Q1) ______involves the use of alkynyl complexes.

A)Heck reaction

B)Stille coupling

C)Suzuki coupling

D)Sonogashira coupling

E)Alkene metathesis

Q2) Which of the following is not a pericyclic reaction?

A)Cope rearrangement

B)Claisen rearrangement

C)Suzuki coupling

D)Diels-Alder reaction

Q3) In the Heck reaction, alkenes with large substituent groups are the most reactive.

A)True

B)False

Q4) Consider diorganocopper reagents and organopalladium compounds. Only the latter is useful in forming new carbon-to-carbon bonds

A)True

B)False

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Chapter 25: Carbohydrates

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Q1) The structures that represent reducing sugars are:

a. only the ketoses.

b. only the aldoses.

c. all of these structures.

Q2) Which of the following is a disaccharide?

A)glucose

B)fructose

C)sucrose

D)mannitol

Q3) Which of the following is an alditol?

A)glucose

B)fructose

C)glucaric acid

D)mannitol

Q4) Which of the following is not a polysaccharide?

A)amylose

B)amylopectin

C)glycogen

D)ribulose

Q5) The enantiomer of ribose is drawn is _______. (D or L)

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Chapter 26: Lipids

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Q1) When soaps disperse in water, the long hydrocarbon tails cluster together in a hydrophobic ball, while the ionic heads on the surface of the cluster stick out into the water. These spherical clusters are called ___________.

Q2) The family of C₂₀ lipids that contain a five-membered ring with two long side chains are called ____________________.

Q3) How many triglycerides (including stereoisomers) are there which contain one molecule of stearic acid, one of myristic acid and one of arachidic acid?

A)3

B)6

C)9

D)12

Q4) Describe how the structure of a phospholipid differs from that of a trigyceride fat, and what influence this difference has on the interaction of these molecules with water.

Q5) Saponification followed by protonation of structure _____ produces two moles of the salt of stearic acid and one mole of the salt of oleic acid.

Q6) Provide the general structure of a triglyceride.

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Page 29

Chapter 27: Amino Acids and Proteins

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Sample Questions

Q1) Which of the following amino acids has a polar side chain?

A)isoleucine

B)valine

C)phenylalanine

D)threonine

Q2) To what structural feature does the term "primary 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

Q3) Bradykinin is a nonapeptide, Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg. In addition to one mole of Arg, the following peptides are present after hydrolysis of bradykinin with chymotrypsin,

Arg-Pro-Pro-Gly-Phe-Ser and Pro-Phe

A)True

B)False

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) Provide the structure of Ser-Phe-Asp.

Q6) Provide the structure of Ser-Ala.

Page 30

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Chapter 28: Nucleic Acids

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Sample Questions

Q1) Which of the following is a definition of transfer RNA (tRNA)?

A)RNA found in the ribosome, the site in cells where synthesis of proteins takes place

B)RNA which carries a specific amino acid to the site of protein synthesis

C)RNA which has coded genetic information

D)RNA which allows transfer of a protein out of a cell

Q2) 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

Q3) Where is the amino acid linked to the ribose unit of transfer RNA in the process of transferring the amino acid to ribosomes?

A)the base

B)C2'-OH

C)3'-OH

D)5'-OH

Q4) Provide the structure of 2-deoxyribose.

Q5) Provide the structure of adenosine triphosphate, ATP.

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) Thermosetting polymers continue to crosslink on heating followed by cooling to irreversibly produce an extremely hard material that cannot be remelted.

A)True

B)False

Q2) What type of intermediate is formed in the polymerization of styrene with AIBN?

A)carbocation

B)carbanion

C)radical

D)organometallic complex

Q3) Which type of polymerization is used to make high density polyethylene (HDPE)?

A)anionic

B)cationic

C)radical

D)Ziegler-Natta

Q4) A good initiator for a free radical addition polymerization is acetyl chloride.

A)True

B)False

Q5) Provide the structure of poly(methyl methacrylate).

Q6) The number of types of monomers in this structure is _______.

Q7) Provide the structure of polystyrene.

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