Chemical Biology Exam Practice Tests - 3751 Verified Questions by Quizplus

Chemical Biology

Exam Practice Tests

Course Introduction

Chemical Biology explores the interface between chemistry and biology, focusing on the use of chemical tools and techniques to study and manipulate biological systems at a molecular level. The course covers the principles of biomolecular structure and function, chemical approaches to probe and modify biological processes, and the design of molecules that can modulate cellular pathways. Topics include chemical synthesis of biomolecules, enzyme mechanisms, drug discovery, chemical genetics, and the application of spectroscopy and imaging in biological research. Through interdisciplinary case studies and experiments, students develop an understanding of how chemical principles are applied to solve biological problems and advance biomedical science.

Recommended Textbook

Organic Chemistry 3rd Edition by David R. Klein

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Page 2

Chapter 1: A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

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Sample Questions

Q1) The carbon and oxygen atoms in carbon monoxide are connected by which type of bond(s)?

A) a sigma ( \(\sigma\)) bond

B) two sigma ( \(\sigma\)) bonds

C) a pi (\(\pi\)) bond

D) two pi (\(\pi\)) bonds

E) both A and D

Answer: E

Q2) Which element has the electron configuration 1s2 2s2 2p6 3s2 3p5?

A) oxygen

B) fluorine

C) sulfur

D) chlorine

E) bromine

Answer: D

Q3) According to molecular orbital theory, the constructive interference of two atomic orbitals results in a(n) _______.

Answer: bonding molecular orbital

Page 3

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Chapter 2: Molecular Representations

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Q1) Draw significant resonance structures for the following compound, CH3CNO. Which of these is/are the most significant resonance structure(s)? Explain why.

Answer: 11ea894b_ac67_aec9_bba7_31df3277d7ef_TB4454_00_TB4454_00 Resonance structure II is most significant, because the more electronegative oxygen atom carries a negative formal charge.

Q2) Draw significant resonance structures for N2O. Which of these is/are the most significant resonance structure(s)? Explain why.

Answer: 11ea894b_ac67_fced_bba7_874e270dd498_TB4454_00_TB4454_00

Resonance structure III is most significant, because the more electronegative oxygen atom carries a negative formal charge.

Q3) What is a resonance hybrid?

Answer: A molecule that can be represented by drawing two or more resonance structures is viewed as a resonance hybrid.

Q4) Draw a bond-line structure for each constitutional isomer with a molecular formula of C2H4O.

Answer: 11ea894b_ac5a_1aa7_bba7_01dafb0d203a_TB4454_00_TB4454_00

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Chapter 3: Acids and Bases

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Sample Questions

Q1) Which of the following solvents can be used with (CH3)3CLi?

A) CH3CH2OH

B) CH3OH

C) H2O

D) Liquid NH3

E) CH3(CH2)4CH3

Answer: E

Q2) Which of the following is not a Brønsted-Lowry acid?

A) CH3OH

B) CH3CH3

C) CH3OCH3

D) CH3SH

E) None of these

Answer: B

Q3) Draw the conjugate acid of CH3OCH3

Answer: 11ea894b_ac6a_bc2d_bba7_b95ff4ea07c8_TB4454_00_TB4454_00

Q4) What is the leveling effect?

Answer: It is the deprotonation of a solvent by a base or protonation of solvent by an acid.

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Chapter 4: Alkanes and Cycloalkanes

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Q1) Identify the size of the hydrocarbon that is used in natural gas.

A) C1 - C4

B) C5 - C12

C) C12 - C18

D) C12 and higher

Q2) What is the structure of [2.2.2]bicyclooctane?

Q3) Draw the lowest energy chair conformer of the most stable isomer of 4-isopropyl-1,2-dimethylcyclohexane.

Q4) Draw a chair conformation of cyclohexane showing all of the equatorial H's.

Q5) Draw a chair conformation of methylcyclohexane.

Q6) Draw the most stable chair conformer of cis-1,4-diethylcyclohexane.

Q7) The process that converts straight-chain alkanes into branched hydrocarbons is called _____________.

A) hydrogenation

B) cracking

C) reforming

D) hydrolysis

Q8) Draw the most stable conformation of trans-1,4-diethylcyclohexane.

Page 6

Q9) Give the structures and IUPAC names of all constitutional isomers of C6H14.

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Chapter 5: Stereoisomerism

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Q1) Identify the hybridization of the middle carbon of an allene.

A) sp

B) sp2

C) sp3

D) sp4

Q2) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -F II. -H III. -OH IV. -SH

Q3) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -CH2CH3 II. -CHCH2 III. -CCH IV. -CH3

Q4) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

I. -CH3 II. -CN III. -CH2OH IV. -Br

Q5) Draw all the isomers with molecular formula C4H8.

Q6) Draw the structure of the compound (S)-3-methylheptane.

Q7) If a sample of carvone gives a specific rotation of 60 and the specific rotation of (R)-carvone is 61, does the unknown sample primarily have the R or S absolute configuration?

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Chapter 6: Chemical Reactivity and Mechanisms

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Q1) Does a reaction with a positive S and a positive H favor reactants or products?

Q2) Does a reaction with a value of 0 for G favor reactants or products?

Q3) In a homolytic bond cleavage, ____ are formed.

A) ions

B) radicals

C) only cations

D) only anions

Q4) Which of the following indicates a reaction with a positive G?

A) endergonic, spontaneous

B) endergonic, not spontaneous

C) exergonic, spontaneous

D) exergonic, not spontaneous

Q5) What is the effect of a catalyst on a reaction?

A) It increases the rate.

B) It decreases the entropy.

C) It changes the equilibrium.

D) It makes the products more stable.

Q6) Draw an energy diagram for an endothermic reaction with two steps.

Q7) Does a reaction with a positive G favor reactants or products?

Page 9

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Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination

Reactions

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Q1) What set of reaction conditions would favor an SN2 reaction on 2-bromo-3-methylbutane?

A) weak nucleophile in a protic solvent

B) weak nucleophile in an aprotic solvent

C) strong nucleophile in a protic solvent

D) strong nucleophile in an aprotic solvent

Q2) Which of the following is a secondary alkyl halide?

A) 1-Bromo-2-methylpropane

B) 2-Bromopropane

C) 1-Bromobutane

D) 2-Bromo-2-methylpropane

Q3) Which of the following is NOT a nucleophile?

A) OH-

B) NH3

C) CH3OH

D) NH4+

E) All of these

Q4) Draw the structure of 3-methylcyclopentene.

Page 10

Q5) Draw the E isomer of 2-methyl-3-heptene.

Q6) Provide the structure for 1-chloro-4-isopropylheptane.

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Chapter 8: Addition Reactions of Alkenes

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Q1) The alkene precursor to ethanol is __________.

Q2) What is a compound that does not have a double bond?

A) allicin (garlic)

B) geraniol (roses)

C) cholesterol

D) limonene (oranges)

E) ammonia

Q3) Identify the best reagents to accomplish a Markovnikov addition of water to an unsymmetrical alkene with minimal skeletal rearrangement.

A) water and dilute acid

B) water and concentrated acid

C) 1. Hg(OAc)2, H2O 2. NaBH4, NaOH

D) 1. BH3 THF 2. H2O2, NaOH

E) 1. OsO4, pyridine 2. NaHSO3, H2O

Q4) Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

A) 2-methyl-1-pentene

B) 2-methyl-2-pentene

C) 4-methyl-2-pentene

D) 4-methyl-1-pentene

E) All of the above

Page 12

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Chapter 9: Alkynes

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Sample Questions

Q1) Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

A) cis-3-hexene

B) trans-2-hexene

C) 3-hexyne

D) 2-hexyne

E) cis-2-hexene

Q2) What reagent(s) are required to prepare trans-2-heptene from 2-heptyne?

Q3) Which of the following alkynes would give a single product under hydroboration-oxidation conditions?

A) 1-hexyne

B) 2-hexyne

C) 3-hexyne

D) A and B would each give a single product

E) A and C would each give a single product

Q4) Provide the IUPAC name for CH3CHBrC C(CH2)3CH3.

Q5) Describe the shape for acetylene.

Q6) Draw all constitutional isomers of the molecular formula C6H10 that are internal alkynes.

Page 13

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Chapter 10: Radical Reactions

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Q1) Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.

Q2) Identify an example of propagation.

A) homolytic cleavage

B) heterolytic cleavage

C) hydrogen abstraction

D) coupling

E) hydrogen addition

Q3) Upon treatment with NBS and irradiation with UV light, 2-isopropyl-3-methyl-1-butene reacts to produce exactly two monobrominated compounds. Draw the products of this reaction.

Q4) Give the arrows to show the second propagation step for the reaction of a chlorine radical with ozone.

Q5) Compound A has molecular formula C6H12. Upon treatment with NBS and irradiation with UV light, exactly two compounds (including stereoisomers), are formed. Suggest a possible structure for compoundA.

Q6) Draw arrows to show termination by coupling of two growing poly(vinyl chloride) chains.

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Chapter 11: Synthesis

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Q1) Propose a synthesis of propanoic acid from acetylene.

Q2) Starting with a primary alkyl bromide, which of the following results in an overall decrease in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond

B) substitute bromide with acetylide, then reduce the alkyne to an alkene

C) substitute bromide with methoxide

D) eliminate hydrogen bromide to produce an alkene, then cleave the double bond

Q3) Which of the following sequences converts 3-methyl-1-pentene into 3-bromo-3-methylpentane?

A) 1. Br2; 2. NaOH; 3. HBr

B) 1. Br2, h\(\upsilon\); 2. H2, Pt

C) 1. H2, Pt; 2. Br2, h\(\upsilon\)

D) 1. NBS, h\(\upsilon\); 2. H2, Pt

E) 1. HBr, ROOR; 2. NaOH; 3. HBr

Q4) For multi-step reactions, which is the best method?

A) two steps

B) three steps

C) four steps

D) five steps

E) six steps

Page 15

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Chapter 12: Alcohols and Phenols

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Q1) Identify the characteristics of the hydroboration-oxidation of an alkene.

A) Markovnikov, with rearrangement possible

B) Markovnikov, with no rearrangement possible

C) anti-Markovnikov, with rearrangement possible

D) anti-Markovnikov, with no rearrangement possible

Q2) Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.

Q3) Give the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol.

Q4) Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide.

A) trans-1-bromo-3-methylcyclopentane

B) cis-1-bromo-3-methylcyclopentane

C) 1-methylcyclopentene

D) 2-methylcyclopentene

E) 3-methylcyclopentene

Q5) Provide the structure for 5-chloro-2-propyl-1-heptanol.

Q6) Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.

Q7) Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane..

Q8) Nature's catalysts are called ________.

Q9) Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol. Page 16

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Chapter 13: Ethers and Epoxides; Thiols and Sulfides

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Q1) Which of the following crown ether solvates sodium ions?

A) 12-crown-5

B) 12-crown-4

C) 15-crown-5

D) 18-crown-6

E) none of these

Q2) Which one of the following reactions would produce t-butyl methyl ether in high yield?

A) t-butyl chloride + sodium methoxide

B) t-butanol + methanol in presence of H2SO4 at 140°C

C) t-butyl bromide + bromomethane in the presence of NaOH

D) sodium t-butoxide + bromomethane

Q3) Identify the mechanism for the Williamson ether synthesis.

A) SN1 mechanism

B) SN2 mechanism

C) E1 mechanism

D) E1 Mechanism

Q4) Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane.

Q5) Provide the structure for tetrahydrofuran.

Q6) Provide the structure for oxane.

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Chapter 14: Infrared Spectroscopy and Mass Spectrometry

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Q1) Which of the following is always true about the base peak in a mass spectrum?

A) the peak corresponding to molecular ion

B) the peak corresponding to the most abundant ion

C) the peak corresponding to lowest m/z

D) the peak corresponding to the cation

E) the peak corresponding to the lowest fragment

Q2) Calculate the degree of unsaturation for C14H14N2O.

A) 4

B) 6

C) 8

D) 10

E) 9

Q3) Which of the following is true about CH3CH3+ ?

A) it is the parent ion of ethane

B) it is a molecular ion of ethane with m/z = 30

C) it is a fragment of propane

D) it is a fragment of butane

E) A and B

Q4) Warmer objects emit more __________ radiation.

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Chapter 15: Nuclear Magnetic Resonance Spectroscopy

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Q1) List the most common nuclei that are used in NMR.

Q2) Which of the following does not display a signal in the DEPT-90, but displays a positive signal in DEPT-135 13C NMR spectroscopy?

A) CH3

B) CH2

C) CH

D) C

E) none of these

Q3) Draw a structure, with a formula of C4H10O, which has an integration of 6H, 2H, 1H, and 1H.

Q4) Which of the following compounds gives a 1H NMR spectrum consisting of only a singlet?

A) 1,1-dichloropropane

B) 1,3-dichloropropane

C) 1,2-dichloropropane

D) 2,2-dichloropropane

E) 1-chloropropane

Q5) Draw a structure, with a formula of C4H9Br, which has an integration of 3H, 2H, 2H, and 2H.

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Chapter 16: Conjugated Pi Systems and Pericyclic Reactions

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Q1) Identify the products of a reaction under kinetic control.

A) the most stable product

B) the product whose formation requires the smallest free energy of activation

C) the product that can be formed in the fewest steps

D) the product that is formed at the fastest rate

E) none of these

Q2) Identify the pericyclic reaction in which two sigma bonds are formed and two pi bonds are broken.

A) sigmatropic rearrangement

B) cycloaddition reaction

C) electrolytic reaction

D) this is not a pericyclic reaction

Q3) Identify the MOs that react to form cyclohexene.

A) HOMO of 1,3-butadiene and LUMO of ethylene

B) LUMO of 1,3-butadiene and LUMO of ethylene

C) HOMO of 1,3-butadiene and HOMO of ethylene

D) LUMO of 1,3-butadiene and LUMO of 1,3-butadiene

E) HOMO of 1,3-butadiene and HOMO of 1,3-butadiene

Q4) Provide the structure for (E)-1,3-pentadiene.

Q5) Provide the structure for (S,E)-3-t-butyl-4-methyl-1,4-hexadiene.

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Chapter 17: Aromatic Compounds

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Q1) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers are difficult to distinguish using 1H NMR, but they can be easily identified using 13C NMR.

Describe how 13C NMR distinguishes these three isomers.

Q2) What is the main difference between an aromatic and antiaromatic compound?

A) Aromatic compounds must be cyclic and planar, but not antiaromatic compounds

B) Aromatic compounds must be monocyclic.

C) Antiaromatic compounds must have a conjugated system with a p orbital at every vertex

D) Aromatic compounds must satisfy Hückel's rule.

E) none of these

Q3) Which of the following annulenes is not aromatic?

A) [6]-annulene

B) [14]-annulene

C) [16]-annulene

D) [18]-annulene

E) [22]-annulene

Q4) What is the structure for p-aminobenzoic acid (PABA)?

Q5) What is the structure for 1,3-diphenylbutane?

Q6) Molecular orbitals of equal energy are referred to as _________ orbitals.

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Chapter 18: Aromatic Substitution Reactions

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Q1) Which of the following substituents will not direct the incoming group to the ortho/para position during electrophilic aromatic substitution?

A) -CH2CH3

B) -CF3

C) -OCH3

D) -NHCH3

E) -Br

Q2) Identify the electrophile in the sulfonation reaction of benzene.

A) SO2+

B) H2SO4

C) SO3+

D) H2SO3

E) SO3

Q3) Identify the electrophile in a Friedel-Crafts alkylation.

A) aluminum chloride

B) carbocation

C) aluminum tetrachloride ion

D) carbanion

E) radical

Q4) Give the preferred products from the nitration of bromobenzene.

Page 23

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Chapter 19: Aldehydes and Ketones

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Q1) Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under acidic conditions?

A) a proton transfer followed by a nucleophilic attack

B) a nucleophilic attack followed by a proton transfer

C) nucleophilic attack is the only step

D) proton transfer is not required

Q2) Suggest a stepwise synthesis for pentanal from butanal.

Q3) Which one of the following compounds will yield 1-hexanol when treated with butylmagnesium bromide followed by acid workup?

A) 1-hexanol

B) formaldehyde

C) propanal

D) oxirane

E) hexanal

Q4) Provide the structure for 4-methylbenzaldehyde.

Q5) Suggest a stepwise synthesis for 5-methyl-2-hexanone from 3-methyl-1-bromobutane.

Q6) Provide the structure for benzophenone.

Q7) Suggest a stepwise synthesis for 1-pentanol from butanal.

Page 24

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Chapter 20: Carboxylic Acids and Their Derivatives

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Q1) Provide the structure for 5-chloro-3-isopropyloctanoic acid.

Q2) A compound with molecular formula C9H10O2 exhibits a triplet at \(\delta\) 1.2 (3H), a quartet at \(\delta\) 2.6 (2H), a doublet at \(\delta\) 7.3 (2H), a doublet at \(\delta\) 8.0 (2H) and a singlet at \(\delta\) 11 (1H) in its 1H NMR spectrum. What is the structure for this compound?

Q3) Methanoic acid is commonly known as ________.

Q4) Provide the structure for benzoyl chloride.

Q5) Give the IUPAC name for oxalic acid.

A) ethanedioic acid

B) propanedioic acid

C) butanedioic acid

D) pentanedioic acid

E) benzoic acid

Q6) Which one of the following is the strongest acid? Explain your choice.

A)2,3-dimethylheptanoic acid

B)3,3-dichlorohexanoic acid

C)4-bromo-3-iodohexanoic acid

D)4-bromo-3-chloroheptanoic acid

E)4-bromo-2-fluorohexanoic acid

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Chapter 21: Alpha Carbon Chemistry: Enols and Enolates

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Q1) Give the organic by-product in a haloform reaction.

Q2) Which one of the following compounds is most acidic?

A) ethyl acetoacetate

B) 2-butanone

C) ethyl pentanoate

D) 1-butanol

E) 3-pentanone

Q3) How many gamma hydrogens are in 2-pentanone?

A) 1

B) 2

C) 3

D) 4

E) 5

Q4) Which of the following bases will completely convert 1,4-cyclohexanedione into an enolate?

A) sodium hydroxide

B) sodium ethoxide

C) LDA

D) sodium hydride

E) both C and D

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Chapter 22: Amines

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Q1) A compound with molecular formula C8H19N exhibits a triplet at \(\delta\) 0.9 (6H), a singlet at \(\delta\) 1.1 (1H), a sextet at \(\delta\) 1.3 (4H), a quintet at \(\delta\) 1.4 (4H) and a triplet at \(\delta\) 2.6 (4H) in its 1H NMR spectrum. Its IR spectrum shows a medium absorption band near 3400 cm-1. Its 13C NMR spectrum showed peaks at \(\delta\) 13.7, \(\delta\) 20.5, \(\delta\) 30.4 and \(\delta\) 49.2. What is the structure for this compound?

Q2) Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?

A) 1-bromopentane

B) 1-bromo-3-methylbutane

C) 2-bromo-3-methylpentane

D) 1-bromo-2,3-dimethylbutane

E) 2-bromo-2,3-dimethylbutane

Q3) Identify the weakest base.

A) 4-chloroaniline

B) 4-nitroaniline

C) 4-aminobenzonitrile

D) aniline

E) 4-aminoanisole

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Chapter 23: Introduction to Organometallic Compounds

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Q1) Starting from vinyl chloride and ________ as the only source of carbon atoms, 1-heptene can be synthesized using a Corey-Posner/Whitesides-House coupling reaction.

A) 1-bromopropane

B) 2-bromopentane

C) 1-bromohexane

D) 1-bromopentane

Q2) Which catalysts are common in the Stille coupling reaction?

A) Pd(PPh3)4

B) Pd (OAc)2

C) PdCl2(PPh3)2

D) All of the above

Q3) Identify the product when formaldehyde reacts with one equivalent of a Grignard reagent.

A) primary alcohol

B) secondary alcohol

C) tertiary alcohol

D) carboxylic acid

E) ketone

Q4) Each intermediate in alkene metathesis is formed by _____ cycloaddition

Page 28

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Chapter 24: Carbohydrates

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Q1) D-mannose when subjected to Wohl degradation followed by Br2/H2O produces the same aldonic acid as does______ when treated with Br2/H2O.

A) D-arabinose

B) D-ribose

C) D-xylose

D) D-lyxose

E) D-threose

Q2) How many stereoisomers are possible for fructose?

A) 8

B) 6

C) 10

D) 3

E) 4

Q3) Five-membered cyclic hemiacetal carbohydrates are called ________.

A) furanose

B) pyranose

C) ketohexose

D) aldohexose

E) none of these

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Chapter 25: Amino Acids, Peptides, and Proteins

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133 Verified Questions

133 Flashcards

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Sample Questions

Q1) When two amino acids are connected to each other, they form ____________.

A) a tripeptide

B) a protein

C) a polypeptide

D) a tetrapeptide

E) a dipeptide

Q2) Identify how disulfide bonds are formed.

A) oxidation of thiol groups

B) joining cysteine residues within a peptide

C) joining cysteine residues between two strands of a peptide

D) all of these

Q3) Which of the following tetrapeptides is not cleaved by trypsin?

A) Gly-Lys-Cys-Phe

B) Cys-Ala-Arg-Ser

C) Gly-Ser-Ile-Lys

D) Ala-Lys-Tyr-Arg

E) Lys-Met-Pro-Ala

Q4) Which of the following amino acids will migrate towards the anode at pH 7?

Glycine: pI = 6.0

Lysine: pI = 9.7

Page 30

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Chapter 26: Lipids

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Sample Questions

Q1) Which of the following is not a class of complex lipids?

A) waxes

B) prostaglandins

C) triglycerides

D) phospholipids

Q2) Which one of the following is a precursor for the synthesis of prostaglandins?

A) arachidonic acid

B) linoleic acid

C) cholesterol

D) linolenic acid

E) biodiesel

Q3) Provide the structure of an optically active triglyceride that produced two myristic acid residues and an oleic acid residue when heated in the presence of an acid.

Q4) Which one of the following is not classified as an eicosanoid?

A) leukotrienes

B) prostaglandins

C) thromboxanes

D) prostacyclins

E) cortisone

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Chapter 27: Synthetic Polymers

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Sample Questions

Q1) Free radical polymerization of ethylene results in _______.

A) LDPE

B) MDPE

C) HDPE

D) B and C

E) none of these

Q2) Which one of the following is (are) a biopolymer?

A) RNA

B) DNA

C) polysaccharides

D) proteins

E) all of these

Q3) Which one of the following is the best classification of the polymer Bakelite?

A) fibers

B) elastomers

C) plasticizers

D) thermoplastics

E) thermosetting resins

Q4) Provide the structure of a region of a random copolymer constructed from ethylene and styrene.

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