Medicinal Chemistry Exam Preparation Guide
Course Introduction
Medicinal Chemistry is the interdisciplinary study that explores the design, synthesis, and development of biologically active compounds, with a primary focus on pharmaceuticals. This course covers the fundamental principles of organic and inorganic chemistry as they pertain to drug structure, activity, and metabolism, as well as the interaction of drugs with molecular targets such as enzymes and receptors. Students examine the processes of lead discovery and optimization, structure-activity relationships (SAR), pharmacokinetics, and the impact of molecular modifications on drug efficacy and safety. Emphasis is placed on modern strategies in drug design, including rational drug design, prodrug development, and an overview of regulatory considerations in pharmaceutical research.
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) Which of the following molecules has the smallest dipole moment?
A)Br<sub>2</sub>
B)NH<sub>3</sub>
C)HCl
D)HBr
E)HI
Answer: A
Q2) Draw condensed structures for the four compounds with formula C<sub>3</sub>H<sub>9</sub>N.
Answer: CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>3</sub> (CH<sub>3</sub>)<sub>2</sub>CHNH<sub>2</sub> (CH<sub>3</sub>)<sub>3</sub>N
Q3) What orbitals overlap to create the H-C bond in CH<sub>3</sub><sup>+</sup>?
A)sp<sup>3</sup>-sp<sup>3</sup>
B)sp<sup>2</sup>-sp<sup>3</sup>
C)s-p
D)s-sp<sup>2</sup>
E)s-sp<sup>3</sup>
Answer: D
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 anions, CH<sub>3</sub>CHBrCO<sub>2</sub><sup>- </sup>or CH<sub>3</sub>CHFCO<sub>2</sub><sup>-</sup> is the stronger base? Explain your choice.
Answer: CH<sub>3</sub>CHBrCO<sub>2</sub><sup>-</sup> is the stronger base. The more electronegative F atom can more effectively delocalize the negative charge via induction. This greater delocalization stabilizes CH<sub>3</sub>CHFCO<sub>2</sub><sup>- </sup>relative to CH<sub>3</sub>CHBrCO<sub>2</sub><sup>-</sup> and makes it a weaker base.
Q2) Identify the most acidic carboxylic acid.
A)ICH<sub>2</sub>COOH
B)BrCH<sub>2</sub>COOH
C)CH<sub>3</sub>COOH
D)FCH<sub>2</sub>COOH
E)ClCH<sub>2</sub>COOH
Answer: D
Q3) Explain why AlCl<sub>3</sub> is a Lewis acid.
Answer: A Lewis acid is an electron pair acceptor. Aluminum in AlCl<sub>3</sub> has an empty p orbital that can accommodate the pair of electrons provided by a Lewis base.
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Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) In the boat conformation of cyclohexane, the "flagpole" hydrogens are located on
A)the same carbon
B)adjacent carbons
C)C-1 and C-3
D)C-1 and C-4
E)none of the above
Answer: D
Q2) The K<sub>eq</sub> for the interconversion for the two chair forms of methylcyclohexane at 25 °C is 18. What % of the chair conformers feature an axial methyl group?
A)95
B)75
C)50
D)25
E)5
Answer: E
Q3) Draw an acceptable structure for 4-isopropyl-2-methylheptane.
Answer: 11ea7d6e_0662_e38e_8568_ad8a579688f1_TB1830_00_TB1830_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) A sample of (+)and (-)-3-chlorohexane has a rotation of -20 degrees. Pure (+)-3-chlorohexane has a rotation of +40 degrees. Calculate the enantiomeric excess and the amount of (-)and (+)-3-chlorohexane in the original sample.
Q2) Briefly describe how two enantiomers might be separated.
Q3) Which of the following is/are optically inactive?
A)a 50-50 mixture of R and S enantiomers
B)a meso compound
C)every achiral compound
D)a racemic mixture
E)all the above
Q4) Which of the following is not true of enantiomers?
A)They have the same melting point.
B)They have the same boiling point.
C)They have the same chemical reactivity with non-chiral reagents.
D)They have the same density.
E)They have the same specific rotation.
Q5) Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate three-dimensional stereochemistry detail properly.
Q6) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.
Page 6
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Chapter 5: Alkenes Thermodynamics and Kinetics
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Sample Questions
Q1) Draw (E)-2-methyl-3-hexen-1-ol.
Q2) 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
Q3) The Arrhenius equation models how the rate constant k ________.
A)increases as both E<sub>a</sub> and T increase B)increases most when E<sub>a</sub> increases and T decreases C)increases most when E<sub>a</sub> decreases and T increases D)increases as both E<sub>a</sub> and T decrease E)increases as reactant concentrations increase
Q4) Why do reactions tend to proceed at a faster rate as T increases?
Q5) Draw the structure of propyl vinyl ether.
Q6) Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.
Q7) Draw the structure of two alkenes with molecular formula C<sub>4</sub>H<sub>8</sub> that do not exhibit cis-trans isomerism.
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Q8) What is the molecular formula of the hydrocarbon that contains 5 carbon atoms, one ring, and one bond?
Chapter 6: Reactions of Alkenes
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Sample Questions
Q1) Give the product for the reaction of 1-butene with methanol in the presence of acid.
A)1-ethoxybutane
B)2-ethoxybutane
C)1-methoxybutane
D)2-methoxybutane
E)1-butanol
Q2) Give the product for the reaction that occurs when 1-pentene is treated with Cl<sub>2</sub>.
A)1-chloropentane
B)2-chloropentane
C)1,1-dichloropentane
D)2,2-dichloropentane
E)1,2-dichloropentane
Q3) Which of the following compounds will react most rapidly with HCl?
A)5-methyl-1-hexene
B)4-methyl-1-hexene
C)(E)-5-methyl-2-hexene
D)(E)-2-methyl-3-hexene
E)2-methyl-2-hexene
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Chapter 7: Reactions of Alkynes Introduction to Multistep Synthesis
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Sample Questions
Q1) How many distinct terminal alkynes exist with a molecular formula of C<sub>5</sub>H<sub>8</sub>?
A)1
B)2
C)3
D)4
E)5
Q2) Draw an acceptable structure for 3-sec-butyl-1-heptyne.
Q3) Give the systematic name for the alkyne Cl<sub>3</sub>CCH<sub>2</sub>CH<sub>2</sub>CCCH<sub>3</sub>.
Q4) Which of the following compounds is the major product when 1-hexyne is treated with excess HBr?
A)1,1-dibromohexane
B)1,1-dibromohexene
C)1,2-dibromohexene
D)1,2-dibromohexane
E)2,2-dibromohexane
Q5) Give the IUPAC name for (CH<sub>3</sub>)<sub>2</sub>C(CH<sub>2</sub>CH<sub>3</sub>)CCCH(CH<sub>3</ sub>)<sub>2</sub>.
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Chapter 8: Electron Delocalization, Resonance, and Aromaticity More
About Molecular Orbital Theory
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Sample Questions
Q1) In which of the following does resonance delocalization of electron density not play a role?
A)allyl cation
B)benzyl anion
C)CO<sub>3</sub><sup>2-</sup>
D)O<sub>3</sub>
E)cyclohexyl radical
Q2) Which of the following is aromatic?
A)cyclopentadienyl cation
B)1,3-cyclohexadiene
C)cyclobutenyl anion
D)1,3,5-hexatriene
E)cycloheptatrienyl cation
Q3) In the acetate ion (CH<sub>3</sub>CO<sub>2</sub><sup>-</sup>), which of the oxygen atoms bears a greater negative charge? Explain your answer.
Q4) What is the major product obtained from the addition of one mole of HCl at high temperature to 1,3-butadiene?
Q5) Draw the LUMO of 1,3,5-hexatriene.
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Chapter 9: Substitution Reactions of Alkyl Halides
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Sample Questions
Q1) Why are vinylic halides unreactive in both S<sub>N</sub>2 and S<sub>N</sub>1 reactions?
Q2) S<sub>N</sub>1 reactions usually proceed with ________.
A)equal amounts of inversion and retention at the center undergoing substitution
B)slightly more inversion than retention at the center undergoing substitution
C)slightly more retention than inversion at the center undergoing substitution
D)complete inversion at the center undergoing substitution
E)complete retention at the center undergoing substitution
Q3) Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?
A)(R)-2-bromo-3-ethylpentane
B)(S)-2-bromo-3-ethylpentane
C)(R)-3-bromo-2-methylpentane
D)(S)-3-bromo-2-methylpentane
E)3-bromo-3-ethylpentane
Q4) Rank the species below in order of leaving group capabilities in S<sub>N</sub>2 reactions (worst leaving group to best):
CH<sub>3</sub>O<sup>-</sup>, H<sub>2</sub>O, C<sub>6</sub>H<sub>5</sub>SO<sub>3</sub><sup>-</sup>, H<sub>2</sub>N<sup>-</sup>.
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Chapter 10: Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
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Sample Questions
Q1) Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.
A)S<sub>N</sub>2 and S<sub>N</sub>1
B)E1 and E2
C)S<sub>N</sub>2 and E2
D)E1 and S<sub>N</sub>1
E)E2 and S<sub>N</sub>1
Q2) What is the major product which results when (2R,3S)-2-chloro-3-phenylbutane is treated with sodium methoxide in methanol?
A)(E)-2-phenyl-2-butene
B)(Z)-2-phenyl-2-butene
C)(S)-3-phenyl-1-butene
D)(R)-3-phenyl-1-butene
E)(R)-2-methoxy-2-phenylbutane
Q3) Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis or the trans, undergoes elimination more rapidly when treated with sodium ethoxide? Explain your answer.
Q4) Show the best way to prepare CH<sub>3</sub>OCH(CH<sub>3</sub>)<sub>2</sub> by an S<sub>N</sub>2 reaction.
Page 12
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Chapter 11: Reactions of Alcohols, Ethers, Epoxides, and
Sulfur-Containing Compounds
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Sample Questions
Q1) Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH<sub>3</sub>(CH<sub>2</sub>)<sub>6</sub>CH<sub>2</sub>OH + HBr
Q2) When 1-pentanol is heated with HCl/ZnCl<sub>2</sub>, 1-chloropentane is the major organic product. This reaction proceeds through an ________ mechanism, and ________ is produced as a byproduct.
A)S<sub>N</sub>1, H<sub>2</sub>O
B)S<sub>N</sub>2, H<sub>2</sub>O
C)S<sub>N</sub>1, H<sub>2</sub>
D)S<sub>N</sub>2, H<sub>2</sub>
E)E2, H<sub>2</sub>
Q3) Draw the tosylate ion and explain why it is a particularly good leaving group.
Q4) 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.
Q5) 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.
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) 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
Q2) Name the organic products that would result from metathesis of 1,8-nonadiene.
Q3) What type of intermediate is present when the Grubbs catalyst and a terminal alkene react?
A)metallocyclobutane
B)Grignard reagent
C)Gilman reagent
D)borate ester
E)permanganate ester
Q4) Complete and balance the following transmetallation reaction.
CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>MgCl + SiCl<sub>4</sub>
Q5) Complete and balance the following reaction.
CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li + CuI
Q6) Name the three major aklene products that result when 1-pentene is treated with Grubbs catalyst.
Page 14
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Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) A radical mechanism is postulated to occur when cyclohexene reacts under which of the following conditions?
A)Br<sub>2</sub>, CCl4
B)H<sup>+</sup>, H<sub>2</sub>O
C)BH<sub>3</sub>THF
D)HBr, peroxide
E)Hg(OAc)<sub>2</sub>, H<sub>2</sub>O
Q2) Explain how CFCs are linked to depletion of stratospheric ozone.
Q3) What sequence of reagents can be used to convert 3,3-dimethylpentane into 3,3-dimethyl-2-pentanone?
Q4) Which is more stable, a tertiary alkyl radical or a benzylic radical? Explain.
Q5) Provide a series of synthetic steps by which (CH<sub>3</sub>)<sub>2</sub>C=CH<sub>2</sub> could be prepared from 2-methylpropane.
Q6) Chlorination of methane can result in a mixture of chlorinated products. What experimental conditions should be used to favor the production of chloromethane over the other chlorinated products?
Q7) Provide the reagents necessary for carrying out the transformation of cyclopentane to cyclopentene.
Page 15
Q8) Explain why alkanes are generally considered unreactive compounds.
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Sample Questions
Q1) Which of the following functional groups typically exhibits a carbonyl stretch at the lowest frequency?
A)amide
B)ester
C)ketone
D)aldehyde
E)ether
Q2) Which region of the electromagnetic spectrum, radio or visible, is characterized by waves of shorter wavelength?
Q3) Which of the following statements is true about a molecular ion?
A)It is a compound that lost a pair of electrons.
B)It is a compound that gained a pair of electrons.
C)It is a compound that gained one electron.
D)It is a compound that lost one electron.
E)It is a compound that carries a free radical and a negative charge.
Q4) Deduce a possible structure for the compound with the IR absorptions below. C<sub>4</sub>H<sub>8</sub>O: 3000, 2800, 2715, 1715 cm<sup>-1</sup>
Q5) Which has the higher speed in a vacuum, ultraviolet or infrared light?
Q6) What does "m/z" stand for and what does it mean?
Q7) Give the m/z ratio of the molecular ion in the mass spectrum of 1-butanol. Page 16
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Chapter 15: Nmr Spectroscopy
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Q1) Which compound has a <sup>1</sup>H NMR spectrum consisting of the following peaks: 0.9 (6H, d), 1.0 (3H, t), 2.2 (2H, q), and 4.0 (1H, septet)?
A)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>O<sub>2</sub>CCH<sub>3</sub> B)(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub> C)(CH<sub>3</sub>)<sub>2</sub>CHO<sub>2</sub>CCH<sub>2</sub>CH<sub>3</sub> D)(CH<sub>3</sub>)<sub>2</sub>CHCO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> E)(CH<sub>3</sub>)<sub>2</sub>CHOCH<sub>2</sub>CH<sub>3</sub>
Q2) How might the proton spectrum of ultrapure dimethylamine, (CH<sub>3</sub>)<sub>2</sub>NH, differ from the spectrum of this compound to which D<sub>2</sub>O has been added?
Q3) Predict the number of signals expected, their splitting, and their relative area in the <sup>1</sup>H NMR spectrum of 1,2-dichloroethane (ClCH<sub>2</sub>CH<sub>2</sub>Cl).
Q4) 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?
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Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Sample Questions
Q1) Provide the structure of propanoic anhydride.
Q2) Provide a detailed, stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.
Q3) o-Phthalic acid produces what acid derivative upon heating?
A)an ester
B)a carboxylate
C)an acid chloride
D)an anhydride
E)an amide
Q4) Which of the following terms best describes the compound below? CH<sub>3</sub>(CH<sub>2</sub>)<sub>12</sub>CO<sub>2</sub>H
A)a fatty acid
B)an oil
C)a wax
D)a soap
E)a phosphatidic acid
Q5) What reagents are used to dehydrate amides to nitriles?
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Q6) Provide the structure of the tetrahedral intermediate in the reaction of sodium methoxide with propanoyl chloride.
Chapter 17: Reactions of Aldehydes and Ketones
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Q1) Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?
A)The carbonyl carbon of an ester is more electrophilic than that of an aldehyde.
B)Aldehydes are more sterically hindered than esters.
C)Once the nucleophile adds to an aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups.
D)The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized.
E)Once the nucleophile adds to an aldehyde, neither H- nor R- can be eliminated since they are strongly basic.
Q2) Diisobutylaluminum hydride (DIBALH)can be used to carry out which of the following conversions?
A)ester to aldehyde
B)carboxylic acid to ester
C)2 alcohol to ketone
D)aldehyde to carboxylic acid
E)ester to ketone
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Q1) Which compound has the lowest pKa?
A)(CH<sub>3</sub>CH<sub>2</sub>O<sub>2</sub>C)<sub>2</sub>CH<sub>2</sub> B)CH<sub>3</sub>CH<sub>2</sub>O<sub>2</sub>CCH<sub>2</sub>CHO C)CH<sub>3</sub>CH<sub>2</sub>COCH<sub>2</sub>CHO D)PhCOCH<sub>2</sub>COCH<sub>3</sub> E)(NC)<sub>2</sub>CH<sub>2</sub>
Q2) Provide a detailed, stepwise mechanism for the acid-catalyzed enolization of acetaldehyde.
Q3) What product results when malonic ester is treated with the following sequence of reagents:
1)NaOCH<sub>2</sub>CH<sub>3</sub>; 2)PhCH<sub>2</sub>Br; 3)H<sub>3</sub>O+, ?
Q4) Enolates are frequently formed by treating an aldehyde or ketone with LDA. However, the LDA must first be generated by reacting diisopropylamine with butyllithium. Why don't chemists just use butyllithium itself to deprotonate the aldehyde or ketone and form the enolate?
Q5) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.
Page 21
Q6) Why is the pKa of acetone 20 while that of ethane is 50? Explain the origin for this difference in acidity.
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Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Q1) Provide the structure of dibenzyl ether.
Q2) What specific electrophile is attacked by benzene when it undergoes nitration?
A)HNO<sub>3</sub>
B)NO<sub>3</sub>
C)NO
D)NO<sub>2</sub>
E)NO<sub>2</sub><sup>+</sup>
Q3) Draw p-aminobenzoic acid.
Q4) Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E<sup>+</sup>.
Q5) Provide the major resonance structures of the ion which results when the most acidic hydrogen of cyclopentadiene is lost.
Q6) What is the principle of microscopic reversibility?
Q7) Which step in the general mechanism for electrophilic aromatic substitution is rate-determining? Explain.
Q8) Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.
Page 23
Q9) Explain why nitrobenzene can be used as a solvent for Friedel-Crafts alkylation.
Q10) Provide the structure of anisole.
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Chapter 20: More About Amines Heterocylic Compounds
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Q1) Provide the structure of thymine; How is it used by organisms?
Q2) Draw the structures of the keto forms of both 2-hydroxypyridine and 4-hydroxypyridine.
Q3) Draw 4-methylisoquinoline.
Q4) Provide a structural representation of oxetane.
Q5) Which of the following statements best describes the meaning of the term alkaloid?
A)heterocyclic natural products with a nitrogen as a heteroatom
B)natural, cyclic hydrocarbons
C)heterocyclic natural products with a sulfur as a heteroatom
D)heterocyclic natural products with an oxygen as a heteroatom
E)natural, cyclic hydrocarbons with alkyl groups
Q6) Draw the structure of piperidine.
Q7) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
Q8) When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?
A)2-position
B)3-position
C)4-position
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Chapter 21: Carbohydrates
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Q1) When a monosaccharide reacts to give the pyranose form from its open-chain form, how many distinct pyranose forms are possible?
A)1
B)2
C)2<sup>n</sup>, where n is the number of carbons present
D)4n + 2, where n is the number of carbons present
E)4
Q2) In solution, glucose exists as ________.
A)the open-chain form only
B)the cyclic hemiacetal form only
C)the cyclic acetal form only
D)an equilibrium mixture of the open-chain form and cyclic acetal forms
E)an equilibrium mixture of the open-chain form and cyclic hemiacetal forms
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) What nucleophilic carbon species is used in the Kiliani-Fischer synthesis?
Q5) Which of the D-aldopentoses yields an optically inactive aldonic acid upon oxidation with bromine water? Explain your answer.
Q6) What orbital interaction is the origin of the anomeric effect?
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Chapter 22: Amino Acids, Peptides, and Proteins
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Q1) Explain the chemistry behind giving a "permanent" to a head of hair.
Q2) Rate the following amino acids in decreasing order of migration towards the cathode (negative electrode)when separated by electrophoresis in a solution of pH= 7.3.
I. lysine: pI= 9.87
II. alanine: pI= 6.02
III. aspartate: pI= 5.95
Q3) Draw vertical lines through the peptide bonds in the decapeptide below that will be cleaved by cyanogen bromide.
Try-Ser-Ala-Met-Ser-Pro-Met-Gly-Gly-Asp
Q4) What amino acid can be obtained by the reductive amination of -ketoglutaric acid, HO<sub>2</sub>CCH<sub>2</sub>CH<sub>2</sub>COCO<sub>2</sub>H?
A)glycine
B)serine
C)lysine
D)aspartic acid
E)glutamic acid
Q5) Draw and name the amino acids which may be described as heterocyclic.
Q6) Draw the predominant form of proline at pH=12.
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Chapter 23: Catalysis
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Q1) Show why typical metal-bound water has a considerably lower pKa than that of water.
Q2) "Being in the right place... can be the most powerful factor of all in determining how fast a reaction goes." In terms of reaction rate theory, this statement refers to the ________ for a reaction.
A)probability factor
B)energy factor
C)resonance effect
D)inductive effect
Q3) Which amino acid component is most likely to serve as a proton donor in an enzyme's active site?
A)methionine
B)glutamic acid
C)valine
D)phenylalanine
E)pyroline
Q4) Offer an explanation of how iodide catalyzes the hydrolysis of 1-chloropropane in aqueous base.
Q5) How does Zn<sup>2+</sup> catalyze the hydrolysis of trifluoroacetate esters?
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Q6) Explain the phenomenon known as molecular recognition. Give an example.
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Chapter 24: The Organic Mechanisms of the Coenzymes
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Q1) Which of the following is not needed for the pyruvate dehydrogenase system?
A)lipoate
B)coenzyme A
C)FAD
D)NAD<sup>+</sup>
E)biotin
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) Which of the following reactions does the coenzyme biotin catalyze?
A)decarboxylation of an -keto acid
B)decarboxylation of an -carboxy acid
C)carboxylation of an -carboxy acid
D)decarboxylation of a carbon adjacent to an ester or keto group
E)carboxylation of a carbon adjacent to an ester or keto group
Q4) What metal ion is also required by biotin-dependent enzymes?
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Chapter 25: The Chemistry of Metabolism
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Q1) 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>.
Q2) Most of the energy provided by chemical nutrients is provided in what stage of catabolism?
Q3) How many isoprene units are in a sesquiterpene?
Q4) Of the following compounds, which are consumed in any step of the glycolytic conversion of glucose to pyruvate: ATP, ADP, NAD<sup>+</sup>, NADH, FAD, FADH<sub>2</sub>, Acetyl-CoA.
Q5) In which stage of catabolism is the citric acid cycle found?
Q6) In the first stage of catabolism, proteins are hydrolyzed to ________.
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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids
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Q1) Show the hydrogen bonding which occurs when guanine and cytosine form a base pair.
Q2) Which of the following reaction sequences best describes the formation of the nucleic acid in the biosynthesis of DNA?
A)nucleophilic attack of a 5'-OH group of one nucleotide on the -phosphorus of another B)nucleophilic attack of a 5'-OH group of one nucleotide on the -phosphorus of another C)nucleophilic attack of a 3'-OH group of a nucleotide on the -phosphorus of another D)nucleophilic attack of a 3'-OH group of one nucleotide on the -phosphorus of another E)nucleophilic attack of a 3'-OH group of one nucleotide on the -phosphorus of another
Q3) What is the major structural difference between a ribonucleoside and a ribonucleotide?
Q4) Draw the structure of UMP.
Q5) Assuming that the human genome with its 3 billion base pairs is entirely in a b-helix, how long is the DNA in a human cell?
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Chapter 27: Synthetic Polymers
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Q1) Draw the structure of Nylon 66.
Q2) Provide the structure of poly(acrylonitrile).
Q3) Which of the following species can best serve as a radical initiator for radical polymerization?
A)ROH
B)ROR
C)ROOR
D)RCOOR
E)RCOOH
Q4) What is the difference between natural rubber and Gutta-percha rubber?
A)Natural rubber is hard and brittle while gutta-percha is soft and rubbery.
B)Natural rubber is natural while gutta-percha is synthetic rubber.
C)Natural rubber has a cis configuration while gutta-percha has a trans configuration.
D)Natural rubber and gutta-percha rubber are enantiomers.
E)The monomer for natural rubber is isoprene while the monomer for gutta-percha is 1,3-butadiene.
Q5) Show the reaction which occurs when benzoyl peroxide is heated.
Q6) Why is chain branching less common in anionic polymerization than in cationic polymerization?
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Chapter 28: Pericyclic Reactions
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Q1) When an allyl cation undergoes a cycloaddition under photochemical 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) What does LCAO stand for?
Q3) Under what conditions would a 1,5-hydrogen shift occur in a sigmatropic rearrangement?
A)thermal conditions
B)photochemical conditions
C)suprafacial pathway
D)A and C
E)B and C
Q4) (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
Q5) What characterizes a pericyclic reaction?
Page 33
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