Course Introduction
Chemical Biology
Exam Answer Key
Chemical Biology explores the intersection of chemistry and biology, focusing on the use of chemical techniques and tools to study and manipulate biological systems. This interdisciplinary course covers topics such as the design and synthesis of small molecules, chemical probes for investigating biological processes, enzyme mechanisms, nucleic acid chemistry, and the development of molecular tools to visualize and control cellular function. Through case studies and research examples, students will learn how chemical approaches can provide unique insights into complex biological questions and contribute to advances in drug discovery, molecular diagnostics, and biotechnology.
Recommended Textbook
Organic Chemistry 7th Edition by Paula Yurkanis Bruice
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Page 2
Chapter 1: Remembering General Chemistry: Electronic
Structure and Bonding
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Sample Questions
Q1) What orbitals are used to form the covalent bonds in butane (CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>)?
Answer: The carbon-carbon bonds are formed by the overlap of two carbon sp<sup>3</sup> hybrid atomic orbitals. The carbon-hydrogen bonds are formed by the overlap of a carbon sp<sup>3</sup> hybrid atomic orbital and a hydrogen s orbital.
Q2) Which of the following contain(s)polar covalent bonds?
A)NH<sub>3</sub>
B)Na<sub>2</sub>O
C)H<sub>2</sub>
D)KF
E)both A and C
Answer: A
Q3) Give the hybridization, shape, and bond angle for each carbon in CH<sub>3</sub>CN.
Answer: CH<sub>3 </sub>- sp<sup>3</sup>, tetrahedral, 109.5; C - sp, linear, 180
Q4) Atoms with the same number of protons but different numbers of neutrons are called ________.
Answer: isotopes
Page 3
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Sample Questions
Q1) Which of the following is the strongest acid?
A)HF
B)H<sub>2</sub>O
C): NH<sub>3</sub>
D)CH<sub>4</sub>
E)CH<sub>3</sub>OH
Answer: A
Q2) When a small amount of hexanoic acid [CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H, pK<sub>a</sub>~4.8], is added to a separatory funnel which contains the organic solvent diethyl ether and water with a pH of 12.0, it is found mainly in the ________ phase as ________.
A)ether; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub><sup>-</sup> B)water;
CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub><sup>-</sup> C)ether; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H D)water; CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H E)none of the above
Answer: B
Page 4
Q3) 2-Propanol is shown below. Draw the structure of its conjugate base. (CH<sub>3</sub>)<sub>2</sub>CHOH
Answer: 11ea7d6e_065f_d637_8568_b5ee2decc99c_TB1830_00_TB1830_00
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Page 5
Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) Draw an acceptable structure for sec-butylcyclopentane.
Answer: 11ea7d6e_0663_a6e8_8568_9fbd0e697fc7_TB1830_00_TB1830_00
Q2) Draw an acceptable structure for 4-t-butyloctane.
Answer: 11ea7d6e_0662_bc7c_8568_1db113d5ac4e_TB1830_00_TB1830_00
Q3) Which of the following statements about the conformers that result from rotation about the C2-C3 bond of butane is correct?
A)The highest energy conformer is one in which methyl groups are eclipsed by hydrogens.
B)The gauche conformer is an eclipsed one.
C)Steric strain is absent in the eclipsed forms.
D)Torsional strain is absent in the eclipsed forms.
E)none of the above
Answer: E
Q4) Draw a Newman projection of the most stable conformation of 2-methylpropane.
Answer: 11ea7d6e_0667_77a0_8568_557d57a7f397_TB1830_00_TB1830_00
Q5) Draw an acceptable structure for 4-isopropyl-2-methylheptane.
Answer: 11ea7d6e_0662_e38e_8568_ad8a579688f1_TB1830_00_TB1830_00
Q6) Draw the most stable conformer of trans-1-ethyl-4-methylcyclohexane.
Answer: 11ea7d6e_0669_7386_8568_27548237baf1_TB1830_00_TB1830_00
Page 6
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.
Q2) How many stereoisomers exist with the following basic connectivity?
BrCH<sub>2</sub>CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>3</sub>
A)0
B)1
C)2
D)4
E)8
Q3) Which of the following is a meso compound?
A)trans-1, 4-dimethylcyclohexane
B)cis-1, 3-dimethylcyclohexane
C)trans-1, 3-dimethylcyclohexane
D)cis-1, 4-dimethylcyclohexane
E)trans-1, 2-dimethylcyclohexane
Q4) A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?
Q5) Provide a perspective drawing of the enantiomer of (2R,3S)-1,2,3-trichloropentane.
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Page 7
Chapter 5: Alkenes Thermodynamics and Kinetics
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Sample Questions
Q1) Which of the following is an allylic alcohol?
A)CH<sub>2</sub>=CHCH<sub>2</sub>OCH<sub>3</sub>
B)CH<sub>2</sub>=CHCH<sub>2</sub>CH<sub>3</sub>
C)HOCH=CHCH<sub>2</sub>CH<sub>3</sub>
D)CH<sub>3</sub>CH=CHCH<sub>2</sub>OH E)CH<sub>2</sub>=CHCH<sub>2</sub>CH<sub>2</sub>OH
Q2) Draw the structure of propyl vinyl ether.
Q3) Draw the curved arrows to show how CH<sub>3</sub>CH=CHCH<sub>3</sub> reacts with HBr to form a carbocation.
Q4) An increase in which of the following will occur if the reaction temperature is increased? I. Energy of activation
II) Collision frequency
III) Fraction of collisions with sufficient energy
A)I and II
B)I and III
C)II and III
D)I, II, and III
E)I
Q5) Draw vinyl bromide.
Q6) Draw the structure of (Z)-1-chloro-2-methyl-2-butene.
Page 8
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Chapter 6: Reactions of Alkenes
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Sample Questions
Q1) What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?
A)2-methylpentane
B)2-methyl-1-pentanol
C)2-methyl-2-pentanol
D)2-methyl-3-pentanol
E)1-methoxypentane
Q2) According to the Hammond Postulate, which of the following is correct?
A)The transition state of an endothermic reaction step will be more reactant-like than product-like.
B)The intermediate of an endothermic reaction step will be more reactant-like than product-like.
C)The transition state of an exothermic reaction step will be more reactant-like than product-like.
D)All transition states are more product-like than reactant-like.
E)All transition states are more reactant-like than product-like.
Q3) What is hyperconjugation, and how does it affect carbocation stability?
Q4) Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-methylcyclopentane as the major organic product.
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Chapter 7: Reactions of Alkynes Introduction to Multistep
Synthesis
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Sample Questions
Q1) Provide the structure of the intermediate which forms in the first step of the reaction of 1-butyne with water in the presence of H<sub>2</sub>SO<sub>4</sub>/HgSO<sub>4</sub>.
Q2) Provide the structure of the major organic produt that results when 2-butyne is treated with H<sub>2</sub> in the presence of Lindlar's Catalyst.
Q3) Describe a sequence of reactions by which CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>COCH<sub>2</sub>CH<sub>3</sub> can be prepared from 1-butyne.
Q4) What two atomic orbitals or hybrid atomic orbitals overlap to form the carbon-carbon bond in ethyne?
A)sp<sup>3</sup>-sp<sup>3</sup>
B)p-p
C)sp<sup>2</sup>-sp<sup>2</sup>
D)s-s
E)sp-sp
Q5) Describe a sequence of reactions by which 3-heptyne can be straightforwardly prepared from acetylene.
Page 10
Q6) Provide the structure of (2E,4E)-2-chloro-2,4-octadiene.
Q7) Draw an acceptable structure for 2-hexyne.
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Chapter 8: Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory
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Sample Questions
Q1) Classify cyclopheptatrienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the network.
Q2) List the criteria which compounds must meet in order to be considered aromatic.
Q3) Excluding the horizontal node which is coincident with the molecular plane, how many nodes are present in <sub>4</sub> of the 1, 3, 5-hexatriene system?
A)6
B)5
C)4
D)3
E)0
Q4) Cyclopentadiene can react with itself in a Diels-Alder reaction. Draw the endo and exo products.
Q5) Draw the s-trans conformation of (2E,4Z)-4-methyl-2,4,-heptadiene.
Q6) What is the hybridization of the central carbon of allene (1,2-propadiene)?
A)sp
B)sp<sup>2</sup>
C)sp<sup>3</sup>
D)p
E)none of the above
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Chapter 9: Substitution Reactions of Alkyl Halides
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Sample Questions
Q1) Which of the following compounds will undergo an S<sub>N</sub>2 reaction most readily?
A)(CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>I
B)(CH<sub>3</sub>)<sub>3</sub>CCl
C)(CH<sub>3</sub>)<sub>2</sub>CHI
D)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub> Cl
E)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>I
Q2) Which of the following iodides undergoes S<sub>N</sub>2 reaction with cyanide (CN<sup>-</sup>)the fastest?
A)1-iodo-3-methylpentane
B)2-iodopentane
C)2-iodo-2-methylpentane
D)3-iodopentane
E)1-iodo-2,2-dimethylpentane
Q3) In each of the pairs below, which is the best nucleophile in alcoholic solvents?
a. CH<sub>3</sub>S<sup>-</sup> or CH<sub>3</sub>O<sup>-</sup> <sup>b. (CH</sup><sub>3</sub><sup>)</sup><sub>2</sub>NH or (CH<sub>3</sub><sup>)</sup><sub>3</sub><sup>N</sup> <sup>c. Cl- or</sup><sup> F-</sup> <sup>d. SCN- or OCN-</sup>
Page 12
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Chapter 10: Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
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Sample Questions
Q1) Starting with 2-butene, which of the following is the best method for preparing 2-butyne?
A)HBr; H<sub>2</sub>/Ni; Zn/H<sup>+</sup>
B)HBr; Zn/H<sup>+</sup>; H<sub>2</sub>/Ni
C)Br<sub>2</sub>/CCl<sub>4</sub>; Zn/H<sup>+</sup>; H<sub>2</sub>/Ni
D)Br<sub>2</sub>/CCl<sub>4</sub>; 2NaNH<sub>2</sub> E)HBr; NaNH<sub>2</sub>
Q2) Which base, ammonia (NH<sub>3</sub>)or triethylamine [(CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>N], would be a better choice for use in converting 1-chlorohexane to 1-hexene? Explain briefly.
Q3) When 2-bromo-3-methyl-1-phenylbutane is treated with sodium methoxide, why is the major product 3-methyl-1-phenyl-1-butene?
A)S<sub>N</sub>2 predominates over E2.
B)E1 predominates over E2.
C)The bulkiness of the methoxide results in the less substituted alkene.
D)The newly formed double bond in this compound is conjugated with the phenyl ring.
E)The less substituted alkene is always more stable than the more substituted alkene.
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Page 13
Chapter 11: Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds
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Sample Questions
Q1) Draw the tosylate ion and explain why it is a particularly good leaving group.
Q2) Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl<sub>2</sub>)?
A)(CH<sub>3</sub>)<sub>3</sub>COH
B)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH C)CH<sub>3</sub>CHOHCH<sub>2</sub>CH<sub>3</sub> D)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH
Q3) Provide the structure of the major organic product which results when naphthalene oxide undergoes rearrangement in the presence of water. Explain the regioselectivity of this rearrangement.
Q4) Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol is heated in the presence of HBr.
Q5) A compound (A)C<sub>4</sub>H<sub>10</sub>O is optically active. (A)reacts with HCl and ZnCl<sub>2</sub> (Lucas test)to form a cloudy product within 10 minutes. Deduce the structure of (A).
Q6) Why are alcohols typically poor electrophiles?
Q7) How are certain arene oxides believed to cause cancer?
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Chapter 12: Organometallic Compounds
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Sample Questions
Q1) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q2) Name the alkyne products that result when 1-pentyne is treated with Schrock catalyst.
Q3) Name the three major aklene products that result when 1-pentene is treated with Grubbs catalyst.
Q4) Name the organic products that would result from metathesis of 2-methyl-1-pentene.
Q5) Which of the following is the strongest base?
A)HOMgBr
B)H<sub>2</sub>O
C)CH<sub>4</sub>
D)CH<sub>3</sub>OH
E)CH<sub>3</sub>MgBr
Q6) What two-word name is given to a reaction that breaks the carbon-carbon double bond and then rejoins the fragments with the double bonds forming in a different location?
Q7) The following alkyl halide could not be used to form a Grignard reagent. Explain. HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Page 15
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Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) How many distinct dichlorination products can result when isobutane is subjected to free radical chlorination?
A)1
B)2
C)3
D)4
E)6
Q2) What reagent can best be used to convert cyclopentene to 3-bromocyclopentene in a single step?
A)Br<sub>2</sub>, h
B)NBS, C)HBr
D)HBr with peroxide E)none of the above
Q3) Which of the following is a chain propagation step in the free radical chlorination of methane?
A)CH<sub>4</sub> + Cl CH<sub>3</sub> + HCl
B)Cl<sub>2</sub> 2 Cl
C)Cl + CH<sub>3</sub> CH<sub>3</sub>Cl
D) CH<sub>3</sub> + CH<sub>4</sub> CH<sub>4</sub> + CH<sub>3</sub>
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Sample Questions
Q1) Give the m/z ratio that corresponds to the molecular ion in the mass spectrum of ethylpropylamine.
Q2) Which compound's carbonyl stretch occurs at the lowest wavenumber?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
B)CH<sub>3</sub>COCH<sub>2</sub>CH<sub>3</sub> C)CH<sub>3</sub>CH<sub>2</sub>CONH<sub>2</sub>
D)CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> E)CH<sub>3</sub>CH<sub>2</sub>COCH<sub>2</sub>CH<sub>3</sub>
Q3) Which of the following methods is most suitable for studying conjugation in molecules?
A)infrared
B)NMR
C)mass spectrometry
D)X-ray
E)UV visible
Q4) Which region of the electromagnetic spectrum, radio or visible, is characterized by waves of shorter wavelength?
Q5) How could you distinguish the mass spectrum of 2,2-dimethylpropane from that of isopentane?
Q6) What technique can be used to determine the molecular formula of a compound? Page 17
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Chapter 15: Nmr Spectroscopy
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Sample Questions
Q1) Why is Fourier transform NMR spectroscopy preferred over continuous wave as a technique for <sup>13</sup>C NMR?
Q2) An unknown compound, C<sub>3</sub>H<sub>5</sub>Cl<sub>3</sub>, gave the following proton NMR data: Doublet at 1.70 ppm (3H) Multiplet at 4.32 ppm (1H) Doublet at 5.85 ppm (1H) What is the structure of the compound?
Q3) Determine the number of signals for 4-methyl-1-propylbenzene in the <sup>1</sup>H NMR spectrum. A)4 B)5 C)6 D)7 E)8
Q4) Deduce the identity of the following compound from the spectral data given. C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>: <sup>1</sup>H NMR, 1.23 (3H, triplet), 2.00 (3H, singlet), 4.02 (2H, quartet); IR, 2980, 1740 cm-1
Q5) What information does a HETCOR spectrum give?
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Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid
Derivatives
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Sample Questions
Q1) Esters and amides are most easily made by nucleophilic acyl substitution reactions on ________.
A)alcohols
B)acid anhydrides
C)carboxylates
D)carboxylic acids
E)acid chlorides
Q2) Which of the following fatty acids cannot be synthesized by mammals but must be included in the diet because it is needed to synthesize arachidonic acid which in turn will synthesize prostaglandins?
A)Lauric acid
B)Palmitic acid
C)Arachidic acid
D)Linoleic acid
E)Oleic acid
Q3) Provide a detailed, stepwise mechanism for the acid-catalyzed transesterification of ethyl acetate with n-propanol.
Q4) Provide a detailed, stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.
Page 20
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Chapter 17: Reactions of Aldehydes and Ketones
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Sample Questions
Q1) Provide the structure of the cyanohydrin that results when 4-heptanone is treated with HCN/KCN.
Q2) Which carbonyl is more susceptible to nucleophilic attack, that of cyclohexanone or that of hexanal? Provide two reasons for your choice.
Q3) Identify the compound whose molecular formula and proton NMR spectra are given below:
C<sub>15</sub>H<sub>14</sub>O; a)triplet, at 2.1 ppm (2H)
b)triplet, at 2.4 ppm (2H)
c)multiplet, at 7.9 - 7.2 ppm (10H)
Q4) By which single-step process can benzene be readily converted into acetophenone?
Q5) Provide the structure of the compound that results when 4-heptanone is treated with peroxyacetic acid.
Q6) Which of the following reagents can be used to reduce acetaldehyde to ethyl alcohol?
A)1) LiAlH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup>
B)1) NaBH<sub>4</sub> 2. H<sub>3</sub>O<sup>+</sup>
C)H<sub>2</sub>/Pt
D)A and D
E)A, B, and C
Page 21
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Sample Questions
Q1) Which of the following could result from the dehydration of an aldol?
A)4-methyl-3-penten-2-one
B)4-methyl-4-penten-2-one
C)4-methyl-5-hexen-2-one
D)4-methyl-4-hexen-2-one
E)3-methyl-4-penten-2-one
Q2) Rank the following compounds in order of increasing acidity of their a-Hs, least acidic to most acidic: CH<sub>3</sub>CH<sub>2</sub>CON(CH<sub>3</sub>)<sub>2</sub>, PhCOCH<sub>2</sub>CHO,
CH<sub>3</sub>CH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>, and PhCOCH<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>.
Q3) Provide a detailed, stepwise mechanism for the base-catalyzed enolization of acetaldehyde.
Q4) Why is the pKa of acetone 20 while that of ethane is 50? Explain the origin for this difference in acidity.
Q5) Provide the structure of the major organic product that results when 4-methylhexanal is heated in base and undergoes and aldol addition followed by a dehydration.
Page 22
Q6) Show how an enolate can add to a carbonyl.
Q7) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.
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Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Sample Questions
Q1) Which of the following fails to produce benzoic acid when heated in the presence of acidic sodium dichromate?
A)1-phenylethanol
B)2-phenylethanol
C)2-phenylheptane
D)2-methyl-2-phenylheptane
E)1-phenylheptanol
Q2) Why must Friedel-Crafts acylation reactions be run with more than a single equivalent of AlCl<sub>3</sub>?
Q3) Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.
Q4) What is the major organic product of the reaction between benzene and isobutyl chloride in the presence of AlCl<sub>3</sub>?
A)tert-butylbenzene
B)isobutylbenzene
C)n-butylbenzene
D)chlorobenzene
E)sec-butylbenzene
Q5) Draw benzyl bromide.
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Chapter 20: More About Amines Heterocylic Compounds
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Q1) Which of the following chloropyridines readily undergo nucleophilic substitution upon treatment with NaCN?
A)2-chloropyridine
B)3-chloropyridine
C)4-chloropyridine
D)both A and B
E)both A and C
Q2) What is the stereochemistry of the product in the acid hydrolysis of trans-2,3-epoxybutane?
Q3) Draw the structures of piperidine and morpholine and explain their relative basicities.
Q4) Draw the structure of piperidine.
Q5) Which of the following lists the correct order of reactivity of the substrates in electrophilic aromatic substitution reactions?
A)thiophene > pyrrole > furan > benzene
B)benzene > furan > thiophene > pyrrole
C)furan > pyrrole > benzene > thiophene
D)benzene > pyrrole > thiophene > furan
E)pyrrole > furan > thiophene > benzene
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Chapter 21: Carbohydrates
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Q1) Provide the structure of the product which results when D-ribose is treated with bromine water.
Q2) Provide the open-chair structures of the two monosaccharides that result when D-threose undergoes the Kiliani-Fischer synthesis.
Q3) Provide the Fischer projection of the open-chain form of the aldonic acid which results when L-glucose is treated with bromine water.
Q4) An optically active D-aldopentose produced an optically active alditol upon treatment with NaBH<sub>4</sub>. When this aldopentose was subjected to a Ruff degradation, a D-aldotetrose was generated. This aldotetrose gave an optically active aldaric acid upon oxidation with HNO<sub>3</sub>. Use these data to provide the structure of the starting D-aldopentose.
Q5) Provide the structure of the more stable chair conformer which results when -D-galactose is treated with excess acetic anhydride/pyridine.
Q6) Draw the Fischer projection for the open-chain form of D-glucose.
Q7) Draw the Fischer projection for the open-chain form of D-erythrose.
Q8) Under what conditions is the methyl glycoside of galactose prepared?
Q9) Draw the Fischer projection for the open-chain form of D-fructose.
Q10) Draw L-erythrose.
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Chapter 22: Amino Acids, Peptides, and Proteins
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Q1) Draw glutamate.
Q2) In a globular protein, would the side chain of aspartic acid most probably be oriented toward the interior of the protein or outward toward the aqueous surroundings? Explain.
Q3) Which of the following is an acceptable name for the peptide sequence shown below? Glu-Glu-His-Val-Cys
A)1,2-diglutamylhistidylvalylcysteine
B)glutamylglutamylhistidylvalylcysteine
C)1-glutamyl-2-glutamylhistidylvalylcysteine
D)diglutamylhistidylvalylcysteine
E)biglutamylhistidylvalylcysteine
Q4) Which of the following amino acids has its isoelectric point at the lowest pH?
A)glutamic acid
B)lysine
C)valine
D)glycine
E)methionine
Q5) Draw the predominant form of proline at pH=12.
Q6) Draw the predominant form of aspartate at physiological pH.
Q7) Draw the form of L-lysine which is present at biological pH.
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Chapter 23: Catalysis
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Q1) Identify the factors that contribute to the catalytic ability of enzymes.
A)proper orientation of the reacting groups
B)some amino acid side chain groups of the enzyme serve as catalysts
C)some amino acid side chains stabilize transition states and intermediates
D)metal ions in enzymes serve as catalysts
E)all of the above
Q2) Explain what is meant by anchimeric assistance and give an example.
Q3) In the hydrolysis of methyl trifluoroacetate, give two purposes of the zinc catalyst.
A)increases the rate of the first step by providing a metal-bound hydroxide ion
B)increases the rate of the second step by decreasing the basicity of the leaving group
C)increases the rate of the second step by increasing the basicity of the leaving group
D)increases the rate of the first step by providing a metal-bound water molecule
E)increases the rate of the last step by replacing alkoxide with hydroxide
Q4) How does a base catalyst increase the rate of reaction?
Q5) Why is histidine a versatile catalytic group?
Q6) What are NAM and NAG and what do they do?
Q7) How does Cu<sup>2+</sup> catalyze the decarboxylation of dimethyloxaloacetate?
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Chapter 24: The Organic Mechanisms of the Coenzymes
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Q1) In a process known as oxidative phosphorylation, every NADH that is formed in carrying out oxidation reactions in the early stages of catabolism is converted into
A)three ATPs
B)two ATPs
C)four FADHs
D)six acetyl-CoAs
E)none of the above
Q2) Which of the following vitamins is involved in the catalysis of an acyl transfer reaction?
A)vitamin B<sub>1</sub>
B)folic acid
C)vitamin B<sub>12</sub>
D)biotin
E)lipoic acid
Q3) Through what enzymatic pathway is thymine biosynthesized?
Q4) What are the main structural and functional differences between NAD<sup>+</sup>/NADH and NADP<sup>+</sup>/NADPH?
Q5) Give the purpose of FAD and FMN.
Q6) What are holoenzymes and apoenzymes?
Page 29
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Chapter 25: The Chemistry of Metabolism
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Q1) At biological pH, ADP has ________ negative charges per molecule.
A)4)0
B)3)3
C)2)8
D)1)1
E)0)6
Q2) a-Ketoglutarate is an intermediate in the citric acid cycle. Draw its structure.
Q3) Most of the energy provided by chemical nutrients is provided in what stage of catabolism?
Q4) Identify the seventh step of the citric acid cycle.
A)Citrate is converted to isocitrate.
B)Conjugate addition of water to the double bond of fumarate forms (S)-malate.
C)Acetyl-CoA reacts with oxaloacetate to form citrate.
D)FAD oxidizes succinate to fumarate.
E)The secondary alcohol of isocitrate is oxidized to a ketone by NAD<sup>+</sup> and the ketone loses CO<sub>2</sub>.
Q5) Why does phosphorylating a carboxylate make it more susceptible to nucleophilic attack?
Q6) In what three areas of the body does first stage catabolism primarily occur?
Q7) In which stage of catabolism is the citric acid cycle found?
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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids
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Q1) How many hydrogen bonds exist between the cytosine/guanine base pairs? A)1 B)2 C)3
D)4
E)5
Q2) List the number of pairs of chromosomes in a human.
A)18 pairs of chromosomes
B)20 pairs of chromosomes
C)23 pairs of chromosomes
D)25 pairs of chromosomes
E)27 pairs of chromosomes
Q3) What is a nucleotide? Give an example.
Q4) Draw the structure of thymidine.
Q5) Show the hydrogen bonding which occurs when guanine and cytosine form a base pair.
Q6) What is meant by semiconservative DNA replication?
Q7) What are the four common ribonucleosides?
Page 31
Q8) A commonly known nucleotide is adenosine 3', 5'-phosphate (cAMP). What is the structure of cAMP?
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Chapter 27: Synthetic Polymers
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Q1) Identify the monomers that undergo anionic polymerization.
A)styrene
B)methyl methacrylate
C)vinyl chloride
D)methyl vinyl ether
E)acrylamide
Q2) What structural characteristic is shared by compounds used as radical initiators?
Q3) The first polymer, invented by A. Parke in 1856, was ________.
A)Polyethlene
B)Polyester
C)Polystyrene
D)Celluloid
E)Teflon
Q4) Provide the structure of poly(vinyl chloride).
Q5) ABS is a copolymer of what three monomers?
Q6) Show how branching could occur during the free-radical polymerization of styrene.
Q7) List the two main groups of polymers and give one example of each.
Q8) What are biodegradable polymers? Give an example.
Page 32
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Chapter 28: Pericyclic Reactions
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Q1) When an allyl anion undergoes a cycloaddition under thermal conditions with ethylene (bonds forming at the ends of the -systems), the cycloaddition is described as ________.
A)[2+2] and suprafacial B)[2+4] and suprafacial C)[2+2] and antarafacial D)[2+4] and antarafacial E)[2+3] and antarafacial
Q2) How many nodes does the highest energy molecular orbital of 1,3,5,7-octatetraene have?
A)4
B)5
C)6
D)8 E)10
Q3) (a) Under thermal conditions, will ring closure of (2E,4Z,6Z,8E)-decatetraene be conrotatory or disrotatory? Explain. (b) Will the product be cis or trans? Explain
Q4) What is meant by frontier orbitals?
Q5) Explain what a node is and how it is formed.
Page 33
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