Advanced Organic Chemistry
Final Exam
Course Introduction
Advanced Organic Chemistry explores the intricate mechanisms, synthetic strategies, and reactivity patterns of organic molecules beyond foundational concepts. This course delves into reaction mechanisms, stereochemistry, spectroscopy, and the design of multi-step syntheses while introducing current research topics and methods in organic synthesis. Students will analyze literature examples, discuss complex functional group interconversions, and examine modern catalysts and reagents, equipping them with the analytical tools and conceptual framework necessary for advanced study or research in organic chemistry.
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 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
Q2) The carbon-carbon double bond in ethene is ________ and ________ than the carbon-carbon triple bond in ethyne.
A)stronger; shorter
B)stronger; longer
C)weaker; shorter
D)weaker; longer
E)stronger; more polar
Answer: D
Q3) How many nonbonding electron pairs, bonding electron pairs, pi bonds, and sigma bonds are present in CO<sub>2</sub>?
Answer: 4 nonbonding electron pairs, 4 bonding electrons pairs, 2 pi bonds, 2 sigma bonds
Page 3
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Chapter 2: Acids and Bases: Central to Understanding Organic Chemistry
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Q1) When a small amount of hexanoic acid [CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CO<sub>2</sub>H, pKa~4.8], is added to a separatory funnel which contains the organic solvent diethyl ether and water with a pH of 2.0, 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: C
Q2) HCN has a pKa = 9.1. What form of the compound, HCN or CN<sup>-</sup>, will predominate in a solution of pH = 7.0
Answer: HCN
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.
Q4) Give the conjugate acid and the conjugate base for HSO<sub>4</sub><sup>-</sup>.
Answer: conjugate acid: H<sub>2</sub>SO<sub>4</sub> conjugate base: SO<sub>4</sub><sup>2-</sup>
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Chapter 3: An Introduction to Organic Compounds
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Sample Questions
Q1) Which conformer is at a local energy minimum on the potential energy diagram in the chair-chair interconversion of cyclohexane?
A)half-chair
B)planar
C)boat
D)twist-boat
E)fully eclipsed
Answer: D
Q2) Draw an acceptable structure for 6-ethyl-2,6, 7-trimethyl-5-propylnonane.
Answer: 11ea7d6e_0663_0a9f_8568_9bf5f032b3cb_TB1830_00_TB1830_00
Q3) Draw the most stable conformer of trans-1-ethyl-4-methylcyclohexane.
Answer: 11ea7d6e_0669_7386_8568_27548237baf1_TB1830_00_TB1830_00
Q4) Draw the Newman projection that represents the least stable conformation of 3,3-dimethylhexane viewed along the C3-C4 bond.
Answer: 11ea7d6e_0667_779e_8568_bf6268fb94bc_TB1830_00_TB1830_00
Q5) Draw the Newman structure for the most stable conformation of 1-bromopropane considering rotation about the C<sub>1</sub>-C<sub>2</sub> bond.
Answer: 11ea7d6e_0667_779f_8568_7d1e9a0d1c0e_TB1830_00_TB1830_00
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Chapter 4: Isomers: the Arrangement of Atoms in Space
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Sample Questions
Q1) Provide a careful structure for (2R,3S)-2,3-dibromohexane.
Q2) Which of the statements below correctly describes an achiral molecule?
A)The molecule has a nonsuperimposable mirror image.
B)The molecule exhibits optical activity when it interacts with plane-polarized light.
C)The molecule has an enantiomer.
D)The molecule might be a meso form.
E)none of the above
Q3) Provide a careful structure for (2S,3S)-2,3-dibromohexane.
Q4) 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
Q5) 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?
Q6) Briefly describe how two enantiomers might be separated.
Q7) 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) The G° for the conversion of "axial" isopropylcyclohexane to "equatorial" isopropylcyclohexane at 298K is -2.1 kcal/mol. Calculate the percentage of isopropylcyclohexane molecules that have the isopropyl substituent in the axial position at this temperature.
[R = 1.987 × 10<sup>-3</sup> kcal mol<sup>-1</sup>K<sup>-1</sup>]
Q2) A hydrocarbon with molecular formula C<sub>20</sub>H<sub>34</sub> has what degree of substitution?<sub> </sub>
A)2
B)3
C)4 D)5 E)6
Q3) Muscalure, the sex attractant of the common housefly, is an acyclic alkene that contains 23 carbons. How many hydrogen atoms are in a molecule of muscalure?
Q4) Draw (E)-2-methyl-3-hexen-1-ol.
Q5) Why do reactions tend to proceed at a faster rate as T increases?
Q6) Draw the structure of propyl vinyl ether.
Q7) Draw all the possible constitutional isomers of C<sub>4</sub>H<sub>8</sub>.
Q8) Draw the structure of (Z)-4-ethyl-3-methylheptene.
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Chapter 6: Reactions of Alkenes
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Q1) Identify the true statements in the mechanism in the addition of water to an alkene.
A)The addition of the electrophile is a slow step.
B)The addition of the nucleophile is a fast step.
C)A carbocation is formed as an intermediate.
D)Water abstracts the extra proton from the protonated alcohol.
E)All of the above
Q2) Based on the relative stabilities of the intermediates involved, explain the basis for Markovnikov's rule in the addition of hydrogen halides to alkenes.
Q3) Give the types of products formed from the bromination and catalytic hydrogenation (using D<sub>2</sub>)of cyclohexene.
Q4) Which statement is true in the oxymercuration-reduction of an alkene?
A)Markovnikov orientation and syn addition occur.
B)Markovnikov orientation and anti addition occur.
C)Anti-Markovnikov orientation and syn addition occur.
D)Anti-Markovnikov orientation and anti addition occur.
E)Markonikov orientation and both syn and anti addition occur.
Q5) Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.
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Chapter 7: Reactions of Alkynes Introduction to Multistep
Synthesis
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Sample Questions
Q1) 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>.
Q2) Describe a sequence of reactions by which cis-2-pentene could be prepared from acetylene.
Q3) Provide the structure of the major organic produt that results when 2-butyne is treated with HgSO<sub>4</sub>/H<sub>2</sub>SO<sub>4</sub> in water
Q4) The reagent needed to convert 2-butyne to trans-2-butene is ________.
A)H<sub>2</sub>/Pt
B)H<sub>2</sub>/Lindlar's catalyst
C)Li/NH<sub>3</sub>
D)Na/NH<sub>3</sub>
E)C or D
Q5) How many distinct terminal alkynes exist with a molecular formula of C<sub>5</sub>H<sub>8</sub>?
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Chapter 8: Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory
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Sample Questions
Q1) Which of the following statements is incorrect about benzene?
A)All of the carbon atoms are sp hybridized.
B)It has delocalized electrons.
C)The carbon-carbon bond lengths are all the same.
D)The carbon-hydrogen bond lengths are all the same.
E)All twelve atoms lie in the same plane.
Q2) When cycloheptatriene is deprotonated, an anion with seven resonance forms of equal energy can be drawn. Given this fact, explain why cycloheptatriene is only slightly more acidic than propene.
Q3) Which of the following ions is most acidic?
A)C<sub>6</sub>H<sub>5</sub>NH<sub>3</sub><sup>+</sup>
B)C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>NH<sub>3</sub><sup>+</sup>
C)(CH<sub>3</sub>)<sub>2</sub>CHNH<sub>3</sub><sup>+</sup>
D)CH<sub>3</sub>CH<sub>2</sub>NH<sub>3</sub><sup>+</sup>
E)CH<sub>3</sub>NH<sub>3</sub><sup>+</sup>
Q4) List the criteria which compounds must meet in order to be considered aromatic.
Q5) Draw the LUMO of 1,3,5-hexatriene.
Q7) Draw the s-cis conformation of (2E,4Z)-4-methyl-2,4,-heptadiene. Page 10
Q6) Cyclic hydrocarbons which can be represented as structures containing alternating single and double bonds are called ________.
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Chapter 9: Substitution Reactions of Alkyl Halides
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Sample Questions
Q1) Which of the following statements concerning S<sub>N</sub>2 reactions of alkyl halides is not correct?
A)The rate of reaction depends on the concentration of the nucleophile.
B)The rate of reaction depends on the concentration of the alkyl halide.
C)The rate of reaction of a particular alkyl bromide depends on the steric accessibility of the carbon of the C-Br bond.
D)All alkyl iodides react more rapidly than all alkyl chlorides.
E)The rate of reaction depends on the relative nucleophilicity of the nucleophile.
Q2) Which of the following is the rate law for S<sub>N</sub>1 mechanisms?
A)Rate = k[Alkyl Halide] [Nucleophile]
B)Rate = k[Nucleophile]
C)Rate = k[Alkyl Halide]
D)Rate = k[Alkyl Halide] [Nucleophile] + k<sub>2</sub>[Alkyl Halide]
E)Rate = k<sub>1</sub>[Alkyl Halide] + k<sub>2</sub>[Nucleophile]
Q3) Identify the alkyl halide that reacts the fastest in a S<sub>N</sub>2 reaction.
A)2-chloro-2-methylpropane
B)2-chlorobutane
C)1-chlorobutane
D)chloromethane
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Chapter 10: Elimination Reactions of Alkyl Halides
Competition Between Substitution and Elimination
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Q1) Which of the following statements is true concerning the E2 reactions of alkyl fluorides?
A)Alkyl fluorides react more readily in E2 reactions than do alkyl iodides.
B)The transition state of this E2 reaction resembles a carbanion rather than an alkene.
C)The C-F bond is the weakest carbon-halogen bond so S<sub>N</sub>2 will always predominate over E2 in the reactions of alkyl fluorides.
D)Alkyl fluorides react to form the most stable carbocation intermediate.
E)Alkyl fluorides cannot adopt the proper stereochemical alignment for an E2 reaction to occur.
Q2) Which sequence of reagents works best to convert 3-hexene to 3-hexyne?
A)1) HCl 2. NaNH<sub>2</sub>
B)1) BH<sub>3</sub>THF 2. HO<sup>-</sup>, H<sub>2</sub>O<sub>2</sub> 3. NaNH<sub>2</sub>
C)1) NaNH<sub>2</sub> 2. HI 3. H<sub>3</sub>O<sup>+</sup>
D)1) Br<sub>2</sub>, CH<sub>2</sub>Cl<sub>2</sub> 2. NaNH<sub>2 </sub>(excess) E)1) Cl<sub>2</sub>, CH<sub>2</sub>Cl<sub>2</sub> 2. NaCN (excess)
Q3) Why is the E1 not a likely mechanism when 1-chloropentane is heated in ethanol?
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Chapter 11: Reactions of Alcohols, Ethers, Epoxides, and
Sulfur-Containing Compounds
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Q1) Which of the following is least likely to be found in the product mixture which results when 2,2-dimethyl-3-pentanol is heated in phosphoric acid?
A)(E)-4, 4-dimethyl-2-pentene
B)(Z)-4, 4-dimethyl-2-pentene
C)2, 3-dimethyl-2-pentene
D)2, 3-dimethyl-1-pentene
E)4, 4-dimethyl-1-pentene
Q2) When dipentyl ether is treated with excess HI, through what type of mechanism(s)does the major product result?
A)S<sub>N</sub>2
B)S<sub>N</sub>1
C)both S<sub>N</sub>1 and S<sub>N</sub>2
D)E1
E)E2
Q3) How are certain arene oxides believed to cause cancer?
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.
Page 14
Q5) Draw the tosylate ion and explain why it is a particularly good leaving group.
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Chapter 12: Organometallic Compounds
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Q1) Provide the structure of the major organic product that results when 1-bromocyclohexene reacts with metallic magnesium in diethyl ether.
Q2) 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?
Q3) Complete and balance the following reaction. CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Li + CuI
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) The following alkyl halide could not be used to form a Grignard reagent. Explain. HO-CH<sub>2</sub>CH<sub>2</sub>-Br
Q6) Provide the balanced equation for the reaction that occurs when bromobenzene is treated with metallic lithium in hexanes.
Q7) Name the three major aklene products that result when 1-pentene is treated with Grubbs catalyst.
Q8) Name the organic products that would result from metathesis of 2-methyl-1-pentene.
Page 15
Q9) Name the organic products that would result from metathesis of 1,8-nonadiene.
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Chapter 13: Reactions of Alkanes, Radicals
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Sample Questions
Q1) When petroleum is distilled, the fraction that contains compounds with 5 to 11 carbons is known as ________.
A)natural gas
B)asphalt
C)diesel oil
D)gasoline
E)jet fuel
Q2) Which of the following represents the best preparation of 2-cyclopentenol from cyclopentane?
A)1) Br<sub>2</sub>, h 2. NaOCH<sub>3</sub> 3. NBS, CCl<sub>4</sub> 4. H<sub>2</sub>O
B)1) NBS, CCl<sub>4</sub> 2. Br<sub>2</sub>, CCl<sub>4</sub> 3. NaOH
C)1) Br<sub>2</sub>, h 2. H<sub>2</sub>O<sub>2</sub>
D)1) NBS, CCl<sub>4</sub> 2. NaOCH<sub>3</sub> 3. H<sub>2</sub>O<sub>2</sub>
E)1) NBS, CCl<sub>4</sub> 2. H<sub>2</sub>O2 3. Br<sub>2</sub>, CCl<sub>4</sub> 4. NaOCH<sub>3</sub>
Q3) What C<sub>5</sub>H<sub>12</sub> isomer will give only a single monochlorination product?
Q4) Explain how CFCs are linked to depletion of stratospheric ozone.
Q5) What role do vitamins C and E play in biological radical reactions?
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Chapter 14: Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy
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Q1) In the mass spectrum of 2-chloropropane, what is the m/z of the molecular ion peak of greatest intensity?
A)63
B)76
C)78
D)80
E)82
Q2) Which m/z peak is expected to be the base peak of cyclopentanol?
A)57
B)43
C)29
D)85
E)86
Q3) Give the m/z ratio of the molecular ion in the mass spectrum of 1-butanol.
Q4) Show the m/z values of the molecular ion and 5 likely fragments for the compound ethyl ether, CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3</sub>
Q5) What technique can be used to determine the molecular formula of a compound?
Page 17
Q6) Which has the higher speed in a vacuum, ultraviolet or infrared light?
Q7) Which compound's C C IR band is weakest, 1-butyne, 2-pentyne, or 3-hexyne? Why?
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Chapter 15: Nmr Spectroscopy
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Q1) Deduce the structure from the data given: C<sub>7</sub>H<sub>16</sub>O; <sup>1</sup>H NMR (integration, coupling): 0.9 (9H, s), 1.5 (2H, t), 3.5 (3H, s), 3.8 (2H, t).
Q2) Deduce the identity of the following compound from the <sup>1</sup>H NMR data given.
C<sub>4</sub>H<sub>7</sub>BrO: 2.2 (3H, singlet), 3.5 (2H, triplet), 4.5 (2H, triplet)
Q3) How many signals would you expect to see in the <sup>1</sup>H NMR spectrum of the following compound? ClCH<sub>2</sub>CH<sub>2</sub>Cl
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 COSY spectrum give?
Q6) Give one reason why <sup>13</sup>C NMR is less sensitive than <sup>1</sup>H NMR.
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Chapter 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
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Q1) Provide a detailed, stepwise mechanism for the reaction of butyrolactone with ammonia.
Q2) Provide the structure of propanoic anhydride.
Q3) How are acyl phosphates produced in the body? What organic byproduct results?
Q4) 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
Q5) 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
Page 20
Q6) Provide a detailed, stepwise mechanism for the reaction of propanoic anhydride with phenol.
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Chapter 17: Reactions of Aldehydes and Ketones
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Q1) By which single-step process can benzene be readily converted into acetophenone?
Q2) Which of the following synthetic routes works best for preparing 4-octene?
A)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH=PPh<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
B)4-bromooctane + NaOCH<sub>3</sub>
C)4-bromooctane + KOC(CH<sub>3</sub>)<sub>3</sub> D)CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>MgBr + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO E)CH<sub>3</sub>CH<sub>2</sub>CH=PPh<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
Q3) Propose a synthesis of 4-phenyl-2-butanol from 3-phenylpropanal.
Q4) Provide the structure of the diethyl acetal of butanal.
Q5) Beginning with sodium acetylide (NaCCH), propose a three-step synthesis of hexanal.
Q6) Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.
Q7) Provide the structure of the cyanohydrin that results when cyclopentanone reacts with HCN.
Q8) Propose a synthesis of 3-methyl-4-heptyn-3-ol from 1-butyne.
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Chapter 18: Reactions at the Alpha Carbon of Carbonyl Compounds
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Q1) Provide a detailed, stepwise mechanism for the -bromination of acetone in base.
Q2) Which of the following compounds will give a positive iodoform test?
A)propanal
B)2-pentanone
C)3-pentanone
D)benzophenone
E)cyclohexanone
Q3) Which of the following routes works best for the preparation of 3-ethylcyclohexanone from cyclohexanone?
A)1) LDA 2. Br<sub>2</sub> 3. CH<sub>3</sub>CH<sub>2</sub>MgBr
B)1)
Br<sub>2</sub>, H<sub>3</sub>O<sup>+</sup> 2. KOC(CH<sub>3</sub>)<sub>3</sub> 3. (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>CuLi 4. H<sub>3</sub>O<sup>+</sup> C)1) Br<sub>2</sub>, H<sub>3</sub>O<sup>+</sup> 2. CH<sub>3</sub>CH<sub>2</sub>OH, D)1) NBS 2. Mg, ether 3. CH<sub>3</sub>CHO
E)1) Br<sub>2</sub>, h 2. NaOH 3. NaOCH<sub>2</sub>CH<sub>3</sub> 4. H<sub>3</sub>O<sup>+</sup>
Q4) What product is formed in the mixed Claisen condensation between methyl benzoate and cyclohexanone?
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Chapter 19: Reactions of Benzene and Substituted
Benzenes
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Q1) Can one distinguish among the three isomeric xylenes using <sup>13</sup>C NMR? Explain.
Q2) Which of the following is the electrophile that attacks the aromatic ring during sulfonation?
A)HSO<sub>3</sub><sup>+</sup>
B)SO<sub>2</sub><sup>+</sup>
C)HSO<sub>3</sub><sup>-</sup>
D)H<sub>2</sub>SO<sub>4</sub>
E)HSO<sub>4</sub><sup>-</sup>
Q3) Draw p-aminobenzoic acid.
Q4) Provide a detailed, stepwise mechanism for the reaction of benzene with Br<sub>2</sub> and FeBr<sub>3</sub>. Make sure to include the activating reaction between Br<sub>2</sub> and FeBr<sub>3</sub> in your mechanism.
Q5) In the bromination of benzene using Br<sub>2</sub> and FeBr<sub>3</sub>, is the intermediate carbocation aromatic? Explain.
Q6) Explain why nitrobenzene can be used as a solvent for Friedel-Crafts alkylation.
Q7) Provide the structure of anisole.
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Q8) Explain why direct nitration of aniline yields, among other products, m-nitroaniline.
Chapter 20: More About Amines Heterocylic Compounds
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Q1) What results when cis-2-butene is subjected to the following reaction sequence: (1) Cl<sub>2</sub>, H<sub>2</sub>O, (2) NaOH, (3) H<sub>3</sub>O<sup>+</sup>?
A)a meso epoxide
B)a 1:1 mixture of enantiomeric epoxides
C)a meso diol
D)a 1:1 mixture of enantiomeric diols
E)2-butanol
Q2) Draw the structure of the aziridinium ion and explain why its pKa is lower than a typical secondary ammonium ion.
Q3) Draw the structure of piperidine.
Q4) Provide the structure of thymine; How is it used by organisms?
Q5) When benzofuran is treated with acetic anhydride, the major organic product is
A)2-acetylbenzofuran
B)3-acetylbenzofuran
C)4-acetylbenzofuran
D)5-acetylbenzofuran
E)7-acetylbenzofuran
Q6) Provide a structural representation of cis-3-ethyl-1,2-epoxycyclopentane.
Page 25
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Chapter 21: Carbohydrates
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Q1) Provide the open-chair structures of the two monosaccharides that result when D-threose undergoes the Kiliani-Fischer synthesis.
Q2) Anomers of D-glucopyranose differ in their stereochemistry at ________.
A)C1
B)C2
C)C3
D)C4
E)C5
Q3) Reduction of a 2-ketohexose with NaBH<sub>4</sub> yields ________.
A)a single aldohexose
B)a mixture of acetals
C)a mixture of alditols
D)a mixture of cyclic hemiacetals
E)a single pyranose
Q4) Which of the following blood types is known as the universal acceptor? A)A B)B
C)AB D)O
E)ABO
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Chapter 22: Amino Acids, Peptides, and Proteins
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Q1) In peptide synthesis, give the use of di-tert-butyl dicarbonate.
A)activates the carboxyl group of an amino acid
B)protects the carboxyl group of an amino acid
C)protects the amino group of an amino acid
D)activates the amino group of an amino acid
E)removes the protecting group on the N-terminal amino acid
Q2) Draw the predominant form of histidine at pH=0.
Q3) What is the net charge of arginine in a solution of pH 1.0?
Q4) Which of the following are capable of denaturing proteins?
A)organic solvents
B)detergents
C)extreme pH
D)heat
E)all of the above
Q5) Provide the Fischer projection of L-aspartic acid.
Q6) Draw structures for the forms of glycine present in basic, neutral, and acidic solutions.
Q7) What is the major force responsible for the formation of an -helix in protein secondary structure?
Q8) Explain the chemistry behind giving a "permanent" to a head of hair.
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Chapter 23: Catalysis
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Q1) Which of the following sets of parameters are all altered when a reaction is carried out in the presence of a catalyst?
A) G°, H°, K<sub>eq</sub>
B)E<sub>a</sub>, free energy of activation, k<sub>rate</sub>
C) G°, k<sub>rate</sub>, K<sub>eq</sub>
D) H°, DS°, E<sub>a</sub>
E) H°, S°, k<sub>rate</sub>
Q2) What factor(s)would affect the rate of an intramolecular reaction?
Q3) Which amino acid component of an enzyme has a chain that can form an imine with the substrate?
A)lysine
B)methionine
C)phenylalanine
D)serine
E)aspartic acid
Q4) Provide the two general ways that metal ions catalyze organic reactions.
Q5) Provide two ways in which acid catalyzes ester hydrolysis.
Q6) How does Cu<sup>2+</sup> catalyze the decarboxylation of dimethyloxaloacetate?
Q7) Why is histidine a versatile catalytic group?
Q8) 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 type of vitamins, water-soluble or lipid-soluble, can cause overdose?
Q2) Which of the following vitamins is the only lipid-soluble vitamin that is known to function as a coenzyme?
A)vitamin A
B)vitamin D
C)vitamin B<sub>1</sub>
D)vitamin C
E)vitamin K
Q3) Which of the following statements is not true about the structure of vitamin B<sub>12</sub>?
A)The structure was determined by Dorothy Hodgkin in 1955 using X-ray crystallography.
B)The structure has an adenosyl group.
C)The structure has a cyano group, HO<sup>-</sup>, or H<sub>2</sub>O.
D)The cyano group is coordinated to cobalt.
E)The structure cannot be synthesized by plants and animals.
Q4) List the four stages of catabolism and briefly explain the significance of each.
Q5) Explain what is meant by a prosthetic group. Give an example.
Q6) Give the purpose of biotin.
Q7) Give the purpose of coenzyme B<sub>12 </sub>in rearrangement reactions.
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Chapter 25: The Chemistry of Metabolism
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Q1) Causing a burning sensation in the muscles, what compound builds up in muscle cells when glycolysis occurs under anaerobic conditions?
Q2) In glycolysis, conversion of a molecule of glucose into 2 molecules of pyruvate results in a net production of ________ molecules of ATP.
A)2
B)3
C)4
D)6
E)12
Q3) The C:H ratio present in most terpenes is ________.
A)1:2
B)2:3
C)1:3
D)3:8
E)5:8
Q4) Give the product from the beta-oxidation of a fatty acyl-CoA.
Q5) In which stage of catabolism is the citric acid cycle found?
Q6) Acetyl-CoA enters the citric acid cycle by reacting with ________ to form
30
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Chapter 26: Nucleosides, Nucleotides, and Nucleic Acids
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Q1) Besides a possible difference in base structure, what is the major structural difference between ribo- and deoxyribonucleosides?
Q2) Draw the structure of dTTP.
Q3) What is a nucleoside? Give an example.
Q4) What is meant by semiconservative DNA replication?
Q5) Which of the following statements best describes the meaning of transcription?
A)It is the synthesis of rRNA from a DNA blueprint.
B)It is synonymous with replication.
C)It is the synthesis of identical copies from a DNA blueprint.
D)It is the synthesis of mRNA from a DNA blueprint.
E)It is the synthesis of tRNA from a DNA blueprint.
Q6) Which of the following metal ions complexes with cellular ATP to neutralize some of its negative charges at the active site of an enzyme in order that nucleophilic substitution reactions proceed rapidly?
A)manganese
B)iron
C)cobalt
D)magnesium
E)calcium
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Chapter 27: Synthetic Polymers
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Q1) Give the monomer for the polymer teflon.
A)propylene
B)acrylonitrile
C)tetrafluoroethylene
D)poly(vinyl acetate)
E)styrene
Q2) Which of the following are characteristic of linear polyethylene?
A)They are branched polymers.
B)They are known as high-density polyethylene.
C)They are soft and flexible polymers.
D)A and B
E)A and C
Q3) From which of the following monomers is neoprene synthesized?
A)(Z)-2-chloro-2-butene
B)(E)-2-chloro-2-butene
C)(E)-1-chloro-1,3-butadiene
D)2-chloro-1,3-butadiene
E)2,3-dichloro-1,3-butadiene
Q4) Provide the structure of poly(tetrafluoroethylene).
Q5) What is the mass of each repeating unit in poly(ethylene)?
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Chapter 28: Pericyclic Reactions
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Q1) Give the conditions for 1,7-hydrogen shifts.
A)suprafacial rearrangement
B)antarafacial rearrangement
C)thermal conditions
D)photochemical conditions
E)all of the above
Q2) How many molecular orbitals are produced from the overlap of four p atomic orbitals?
A)2
B)8
C)4
D)16
E)1
Q3) What are the three most common pericyclic reactions? Give examples.
Q4) What does LCAO stand for?
Q5) Electrocyclic reactions are reversible. The cyclic compound is favored for electrocyclic reactions that form six-membered rings, whereas the open-chain compound is favored for reactions that form four-membered rings. Explain thoroughly in terms of the enthalpy changes that are occurring.
Q6) Explain what a node is and how it is formed.
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