Organic Chemistry II
Question Bank
Course Introduction
Organic Chemistry II builds upon the foundational principles introduced in Organic Chemistry I, delving deeper into the structure, properties, and reactivity of organic molecules. This course focuses on advanced topics such as aromaticity, electrophilic and nucleophilic aromatic substitution, carbonyl chemistry, amines, and the mechanisms of important organic reactions. Students will explore concepts related to the synthesis and characterization of complex organic compounds, as well as spectroscopy and modern analytical techniques. Applications to pharmaceuticals, biochemistry, and materials science are also discussed, providing a comprehensive understanding of the role of organic chemistry in various scientific fields.
Recommended Textbook
Organic Chemistry 3rd Edition by David R. Klein
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Chapter 1: A Review of General Chemistry: Electrons, Bonds, and
Molecular Properties
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Sample Questions
Q1) The difference between valence bond theory and molecular orbital (MO) theory is
A) valence bond theory requires the linear combination of atomic orbitals
B) MO theory requires the linear combination of atomic orbitals
C) valence bond theory considers only individual atomic orbitals
D) Both A and B
E) Both B and C
Answer: E
Q2) According to molecular orbital theory the lowest energy molecular orbital that is unoccupied with an electron is referred to as _______.
A) degenerate
B) antibonding
C) the LCAO
D) the LUMO
E) the HOMO
Answer: D
Q3) According to molecular orbital theory, the destructive interference of two atomic orbitals results in a(n) _______.
Answer: antibonding molecular orbital
Page 3
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Chapter 2: Molecular Representations
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Sample Questions
Q1) Draw the resonance hybrid of C<sub>6</sub>H<sub>6</sub>.
Answer: 11ea894b_ac68_7222_bba7_55525f20a2a7_TB4454_00_TB4454_00
Q2) The spreading of positive or negative charge over two or more atoms in a compound is called_______.
A) isomerism
B) delocalization
C) stereoisomerism
D) localization
E) None of these
Answer: B
Q3) Draw a bond-line structure for each constitutional isomer with molecular formula C<sub>4</sub>H<sub>10</sub>O.
Answer: 11ea894b_ac5a_8fdb_bba7_8bcc5aebc515_TB4454_00_TB4454_00 11ea894b_ac5a_8fdc_bba7_e3d8190b09e5_TB4454_00_TB4454_00
Q4) 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.
Q5) Draw two resonance structures for HN<sub>3</sub>.
Answer: 11ea894b_ac66_eb6c_bba7_4f79b39b0027_TB4454_00_TB4454_00
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Chapter 3: Acids and Bases
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Sample Questions
Q1) In a Brønsted-Lowry acid-base reaction, the products are _______.
A) Brønsted-Lowry acid and Brønsted-Lowry base
B) Brønsted-Lowry acid and conjugate base
C) Brønsted-Lowry base and conjugate acid
D) conjugate acid and conjugate base
E) Brønsted-Lowry acid and conjugate acid
Answer: D
Q2) What is the counterion in NaOCH<sub>2</sub>CH<sub>3</sub>?
A) Na<sup>+</sup>
B) NaO<sup>-</sup>
C) CH<sub>3</sub>CH<sub>2</sub><sup>-</sup>
D) CH<sub>3</sub>CH<sub>2</sub>O<sup>-</sup>
Answer: A
Q3) Which of the following compounds is more acidic? Explain why. CH<sub>3</sub>OH and CH<sub>3</sub>NH<sub>2</sub>
Answer: CH<sub>3</sub>OH is more acidic than CH<sub>3</sub>NH<sub>2</sub>. The conjugate base CH<sub>3</sub>O<sup>-</sup> is more stable than CH<sub>3</sub>NH<sup>-</sup>, because oxygen is more electronegative than nitrogen and can<sub> </sub>stabilize the negative charge better, resulting in a weak conjugate base.
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Chapter 4: Alkanes and Cycloalkanes
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Sample Questions
Q1) What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol?
Q2) Give the structures and IUPAC names of all constitutional isomers of C<sub>6</sub>H<sub>14</sub>.
Q3) Draw the most stable chair conformer of the most stable isomer of 1,3,5-trimethylcyclohexane.
Q4) The process that converts straight-chain alkanes into branched hydrocarbons is called _____________.
A) hydrogenation
B) cracking C) reforming D) hydrolysis
Q5) What is the structure of [2.2.2]bicyclooctane?
Q6) What is the structure of 1-cyclopropyl-3-methylcyclopentane?
Q7) Draw a chair conformation of ethylcyclohexane with the ethyl group axial.
Q8) Draw the most stable chair conformer of cis-1,4-diethylcyclohexane.
Q9) Draw an energy diagram for the conformational analysis of propane.
Q11) What is the structure of an isopropyl group? Page 6
Q10) Draw a chair conformation of methylcyclohexane.
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Page 7
Chapter 5: Stereoisomerism
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Sample Questions
Q1) 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?
Q2) Draw all the isomers with molecular formula C<sub>4</sub>H<sub>6</sub>.
Q3) Identify the hybridization of the middle carbon of an allene.
A) sp
B) sp<sup>2</sup>
C) sp<sup>3</sup>
D) sp<sup>4</sup>
Q4) When a racemic mixture is reacted with a single enantiomer of another compound, then a pair of _________ is formed.
A) identical compounds
B) enantiomers
C) diastereomers
D) none of the above
Q5) If a sample of carvone gives a specific rotation of 0 and the specific rotation of pure (R)-carvone is 61, what is the configuration of the unknown sample?
Q6) Draw the structure of the compound (R)-4-ethyloctane.
Q7) Draw all the isomers with molecular formula C<sub>4</sub>H<sub>8</sub>.
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Chapter 6: Chemical Reactivity and Mechanisms
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Sample Questions
Q1) Predict the sign of G for an exothermic reaction with an increase in entropy.
A) positive
B) negative
C) no change
D) cannot predict without additional information
Q2) Does a reaction with a value of 0 for G favor reactants or products?
Q3) In a heterolytic bond cleavage, ____ are formed.
A) ions
B) radicals
C) only cations
D) only anions
Q4) Draw an energy diagram for an endothermic reaction with two steps.
Q5) Does a reaction with a positive S and a positive H favor reactants or products?
Q6) Predict the sign of G for an exothermic reaction with a decrease in entropy.
A) positive
B) negative
C) no change
D) cannot predict without additional information
Q7) Draw an energy diagram for an exothermic three-step reaction.
Page 9
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Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination
Reactions
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Sample Questions
Q1) Identify which of the following that is NOT an effect of adrenaline.
A) increases heart rate
B) elevates sugar level
C) provides boost of energy
D) increases level of oxygen
E) makes one sleepy
Q2) Which of the following is a weak nucleophile?
A) OH<sup>-</sup>
B) H<sub>2</sub>O
C) CH<sub>3</sub>O<sup>-</sup>
D) NH<sub>4</sub><sup>+</sup>
E) All of these
Q3) Which of the following is a strongest nucleophile in a polar protic solvent?
A) F<sup>-</sup>
B) Cl<sup>-</sup>
C) OH<sup>-</sup>
D) SH<sup>-</sup>
E) All of these
Q4) Draw the E isomer of 2-methyl-3-heptene.
Q5) Provide the structure for cis-1,2-dibromocyclopentane.
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Chapter 8: Addition Reactions of Alkenes
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Sample Questions
Q1) Identify the description of the regioselectivity and stereospecificity in the acid-catalyzed hydration of an alkene.
A) Markovnikov orientation with syn-addition
B) Markovnikov orientation with anti-addition
C) anti-Markovnikov orientation with syn-addition
D) anti-Markovnikov orientation with anti-addition
E) Markovnikov orientation with both syn- and anti-addition
Q2) Give the best description of the regioselectivity and stereospecificity in the oxymercuration of an alkene.
A) Markovnikov orientation with syn-addition
B) Markovnikov orientation with anti-addition
C) anti-Markovnikov orientation with syn-addition
D) anti-Markovnikov orientation with anti-addition
E) Markovnikov orientation with both syn- and anti-addition
Q3) Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and MCPBA, followed by aqueous acid.
Q4) The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is named after which chemist?
Q5) The alkene precursor to acetone is __________.
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Chapter 9: Alkynes
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Sample Questions
Q1) How many distinct eight-carbon hydrocarbon products would be formed in the complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne, in the presence of a palladium catalyst?
A) 1
B) 2
C) 3
D) 6
E) 8
Q2) Provide the IUPAC name for Cl<sub>3</sub>C(CH<sub>2</sub>)<sub>4</sub>C CH.
A) 4,4,4-trichloro-1-butyne
B) 1,1,1-trichloro-6-heptyne
C) 1,1,1-trichloro-5-heptyne
D) 6,6,6-trichloro-1-hexyne
E) 7,7,7-trichloro-1-heptyne
Q3) Select the best reagent expected to convert 3-heptyne to cis-3-heptene.
A) NaNH<sub>2</sub>, NH<sub>3</sub>
B) Na, NH<sub>3</sub>
C) H<sub>2</sub>, Lindlar's catalyst
D) Both A and C
E) Both B and C
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Chapter 10: Radical Reactions
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Sample Questions
Q1) Cyclic compound A has molecular formula C<sub>5</sub>H<sub>10</sub> and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.
Q2) Both compounds A and B have molecular formula C<sub>6</sub>H<sub>14</sub>. Monochlorination of compound A results in the formation of two constitutional isomers. Monochlorination of compound B results in the formation of four constitutional isomers. Identify compounds A and B, and show the products of each monochlorination.
Q3) When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the proton-decoupled <sup>13</sup>C NMR spectrum are observed in the product?
Q4) Which monomer is used for the synthesis of poly(vinyl chloride)?
A) 1-chloroethene
B) 1-chloroethane
C) 1,2-dichloroethene
D) 1-chloro-1-propene
Q5) Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts to produce exactly six monobrominated compounds. Draw the products of this reaction.
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Page 13
Chapter 11: Synthesis
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Sample Questions
Q1) Propose a synthesis of propanoic acid from acetylene.
Q2) Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.
Q3) Identify the best solvent for Green Chemistry.
A) methylene chloride
B) water
C) ethanol
D) methanol
E) ethyl acetate
Q4) Identify the statement that is not part of Green Chemistry.
A) Energy efficiency.
B) Renewable feedstocks.
C) Reuse solvents without purification.
D) Prevent waste.
E) Use catalysts, rather that stoichiometric reagents.
Q5) Devise a synthetic route to convert ethylene into PVC (polyvinyl chloride).
Q6) Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.
Q7) Propose a synthesis of 1-butene from propyne.
Q8) Devise a synthetic route to prepare 1,3-dibromopropan-2-ol from propene.
Q10) Devise a synthetic route to prepare 1,7-heptanediol from propene. Page 14
Q9) Devise a synthetic route to prepare 3-bromo-1-propanol from propene.
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Page 15
Chapter 12: Alcohols and Phenols
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Sample Questions
Q1) What is the IUPAC name for the following compound?
HOCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH
A) 1,2-butanediol
B) isopropyl alcohol
C) 1-propanol
D) 1,3-propanediol
E) 1,2-ethanediol
Q2) Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.
Q3) Identify the type of bonding between molecules of alcohol.
A) ion-ion
B) van der Waals forces
C) hydrogen bonding
D) ion-dipole
E) London dispersion
Q4) Explain why cyclohexanol has a pK<sub>a</sub> of 18 and phenol has a pK<sub>a</sub> of 10. Use structural drawings to explain your reasoning.
Q5) Give the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol.
Q6) Provide the structure for 5-chloro-2-propyl-1-heptanol.
Q7) Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane..
Page 16
Q8) Nature's catalysts are called ________.
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Chapter 13: Ethers and Epoxides; Thiols
and Sulfides
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Sample Questions
Q1) Provide the structure for tetrahydrofuran.
Q2) Which one of the following compounds will have the highest boiling point?
A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH
C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub>
D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cl
E) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OH
Q3) Explain why long-term storage of ethers can be dangerous.
Q4) Which of the following crown ether solvates potassium ions?
A) 12-crown-5
B) 12-crown-4
C) 15-crown-5
D) 18-crown-6
E) none of these
Q5) Can you prepare diisopropyl ether as the major product by heating 2-propanol in the presence of sulfuric acid? Explain your answer.
Q6) Provide the structure for (R)-2,2,3-trimethyl-3-phenyloxirane.
Q7) Provide the structure for oxetane.
Page 17
Q8) The polyethers that function like crown ethers are called _________.
Q9) What is the correct structure for 3-methyl-1-hexanethiol?
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Page 18
Chapter 14: Infrared Spectroscopy and Mass Spectrometry
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Sample Questions
Q1) Calculate the degree of unsaturation for C<sub>11</sub>H<sub>8</sub>ClBrO.
A) 4
B) 6
C) 7
D) 8
E) 10
Q2) Which molecular formula is consistent with the following mass spectral data? M<sup>+</sup> <sup> </sup>at m/z = 108, relative height = 61.5% (M+1)<sup>+</sup> <sup> </sup>at m/z = 109, relative height = 1.5% (M+2)<sup>+</sup> <sup> </sup>at m/z = 110, relative height = 61.3%
A) C<sub>2</sub>H<sub>5</sub>Br
B) C<sub>5</sub>H<sub>12</sub>Cl
C) C<sub>8</sub>H<sub>12</sub>
D) C<sub>2</sub>H<sub>7</sub>Br
E) none of these
Q3) A compound with molecular formula C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>, shows absorptions at 2500-3300 cm<sup>-1</sup> (broad), 1720 cm<sup>-1</sup> and at 1200 cm<sup>-1</sup> on the IR spectrum. Propose a possible structure for this compound.
Q4) Warmer objects emit more __________ radiation.
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Chapter 15: Nuclear Magnetic Resonance Spectroscopy
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Sample Questions
Q1) Which of the following is true about the shape (multiplicity) of the signal in a <sup>1</sup>H NMR spectrum?
A) it indicates the number of neighboring protons
B) it indicates the electronic environment of neighboring protons
C) it indicates the number of different protons
D) it indicates the electronic environment of absorbing protons
E) it indicates the number of protons in the signal
Q2) Which of the following compounds will display a singlet, a triplet and a quartet in its <sup>1</sup>H NMR spectrum?
A) 2-chloro-4-methylpentane
B) 3-chloro-2-methylpentane
C) 3-chloropentane
D) 1-chloro-2,2-dimethylbutane
E) 3-chloro-3-methylpentane
Q3) Which of the following type(s) of protons are chemically non-equivalent?
A) homotopic
B) enantiotopic
C) diastereotopic
D) A & B
E) B & C
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Chapter 16: Conjugated Pi Systems and Pericyclic Reactions
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Sample Questions
Q1) Provide the structure for (S,E)-3-t-butyl-4-methyl-1,4-hexadiene.
Q2) How many electrons does the HOMO of 2,4-hexadiene have in its ground state?
A) 1
B) 2
C) 3
D) 4
E) 0
Q3) 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
Q4) Dienes with adjacent bonds are classified as ______.
A) isolated
B) cumulated
C) skipped
D) conjugated
E) none of these
Q5) Provide the structure for (Z)-2-methyl-2,4-hexadiene.
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Chapter 17: Aromatic Compounds
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Sample Questions
Q1) Which of the following is another name for 4-chlorobenzaldehyde?
A) o-chlorobenzaldehyde
B) m-chlorobenzaldehyde
C) p-chlorobenzaldehyde
D) styrene
E) 1-chlorobenzaldehyde
Q2) Provide the reagents necessary to convert ethylbenzene to styrene.
Q3) Identify the aromatic hydrocarbon with the highest stabilization energy.
A) phenanthrene
B) benzene
C) naphthalene
D) anthracene
Q4) Identify the aromatic hydrocarbon with the highest stabilization energy per ring.
A) phenanthrene
B) benzene
C) naphthalene
D) anthracene
Q5) What is the structure for styrene?
Q6) What is the structure for 1,3-diphenylbutane?
22
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Chapter 18: Aromatic Substitution Reactions
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Sample Questions
Q1) Which of the following compounds will yield the ortho substituted compound as the major product for a nitration reaction?
A) toluene
B) ethylbenzene
C) cumene
D) t-butylbenzene
E) none of these
Q2) Cyclohexene undergoes an addition reaction with bromine, but benzene does not. Instead, benzene undergoes a substitution reaction with bromine. Explain why.
Q3) Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E<sup>+</sup>).
Q4) Which of the following criteria is necessary for a nucleophilic aromatic substitution reaction?
A) the ring must contain a very strong electron withdrawing group
B) the ring must contain a leaving group
C) the leaving group must be ortho or para to the electron withdrawing group
D) the leaving group must be meta to the electron withdrawing group
E) A, B and C
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Page 23
Chapter 19: Aldehydes and Ketones
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Sample Questions
Q1) Provide the structure for (S)-3-chlorocyclohexanone.
Q2) The <sup>1</sup>H NMR spectrum of a compound with formula C<sub>7</sub>H<sub>14</sub>O shows a singlet at 9.2 ppm. Which one of the following is a possible structure for this compound?
A) 2-methyl-3-hexanone
B) 2-methylhexanal
C) 2,2 -dimethylpentanal
D) 2,2-dimethyl-3-pentanone
E) B & C
Q3) Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.
Q4) Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.
Q5) 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
Q6) 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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Sample Questions
Q1) Which one of the following is the strongest acid?
A) benzoic acid
B) 4-nitrobenzoic acid
C) 4-ethylbenzoic acid
D) 4-chlorobenzoic acid
E) 4-hydroxybenzoic acid
Q2) Ethanoic acid is commonly known as ________.
Q3) Provide the structure for (3S,4S)-3-hydroxy-4-phenylnonanoic acid.
Q4) Give the IUPAC name for oxalic acid.
A) ethanedioic acid
B) propanedioic acid
C) butanedioic acid
D) pentanedioic acid
E) benzoic acid
Q5) Provide the structure for 5-chloro-3-isopropyloctanoic acid.
Q6) Methanoic acid is commonly known as ________.
Q7) Provide the structure for 3-ethylbenzonitrile.
Q8) Provide the structure for benzoyl chloride.
Q9) Provide the structure for benzyl propionate.
Q10) Provide the structure for cyclopentanecarbonyl chloride. Page 25
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Chapter 21: Alpha Carbon Chemistry: Enols and Enolates
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Sample Questions
Q1) Which one of the following compounds is most acidic?
A) ethyl acetoacetate
B) 2-butanone
C) ethyl pentanoate
D) 1-butanol
E) 3-pentanone
Q2) Explain why CH<sub>3</sub>ONa should not be used for Claisen condensation of ethylbutanoate.
Q3) An intermolecular Claisen condensation is called a _____________.
Q4) Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?
A) butanal
B) 2-methylbutanal
C) 3-methylpentanal
D) 2,2-dimethylbutanal
E) pentanal
Q5) Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.
Q6) Provide the structure of the enolate when acetophenone is treated with a strong base.
Page 27
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Chapter 22: Amines
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Sample Questions
Q1) What is the structure for 3-chloro-N-ethyl-1-pentanamine?
Q2) Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.
Q3) Identify the weakest base.
A) 4-chloroaniline
B) 4-nitroaniline
C) 4-aminobenzonitrile
D) aniline
E) 4-aminoanisole
Q4) What is the structure for N-ethylbenzylamine?
Q5) A compound with molecular formula C<sub>8</sub>H<sub>19</sub>N 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 <sup>1</sup>H NMR spectrum. Its IR spectrum shows a medium absorption band near 3400 cm<sup>-1</sup>. Its <sup>13</sup>C 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?
Q6) Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.
Q7) What is the structure for N,N-diethylaniline?
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Chapter 23: Introduction to Organometallic Compounds
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Sample Questions
Q1) Which of the following compounds has the least nucleophilic carbon atom?
A) CH<sub>3</sub>CH<sub>2</sub>MgBr
B) CH<sub>3</sub>CH<sub>2</sub>MgI
C) (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>Zn
D) (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>Cu
Q2) What functional group typically results when an organocopper compound (lithium organocuprate) reacts with an acid chloride?
Q3) Which of the following statements is(are) true regarding the preparation of Gilman reagents?
A) Gilman reagents can be made from alkyl halides (R-X).
B) Gilman reagents can be made from aryl halides (Ar-X).
C) Gilman reagents can be made from organolithium reagents.
D) Lithium halides are byproducts of the reaction to make Gilman reagents.
E) all of the above
Q4) Which of the following statements is false?
A) Carbenes are generally long lived.
B) Carbenes have a carbon with non-bonding electrons.
C) Carbenes have a carbon missing an octet.
D) Carbenes can be formed by -elimination.
E) Carbenes are electrophilic.
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Chapter 24: Carbohydrates
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Q1) Five-membered cyclic hemiacetal carbohydrates are called ________.
A) furanose
B) pyranose
C) ketohexose
D) aldohexose
E) none of these
Q2) Identify the most common aldohexose.
Q3) Identify the monosaccharide(s) in \(\beta\)-lactose.
Q4) When D-erythrose is treated with NaBH<sub>4</sub>/H<sub>2</sub>O, it forms _______.
A) a racemic mixture of alditols
B) a meso alditol
C) an optically active alditol
D) an optically active aldonic acid
E) none of these
Q5) Draw the Haworth projection for \(\beta\)-D-erythrofuranose.
Q6) Draw the chair conformation of \(\alpha\)-D-galactopyranose.
Q7) Epimers are diastereomers that differ from each other in the configuration of ____ chiral center(s).
Q8) Draw a Fisher projection for D-fructose.
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Chapter 25: Amino Acids, Peptides, and Proteins
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Q1) A peptide with 12 amino acid residues produced the following fragments when treated with trypsin and chymotrypsin. Edman degradation of this peptide produced the phenylthiohydantoin derivative of glycine. What is the structure of this peptide?
Trypsin: Gly-Leu-Phe-Arg, Cys-Tyr-Ile-Gly, Val-Trp-Ser-Lys
Chymotrypsin: Gly-Leu-Phe, Ser-Lys-Cys-Tyr, Ile-Gly, Arg-Val-Trp,
Q2) Proteins that catalyze biochemical reactions are called ______.
A) apoproteins
B) peptides
C) enzymes
D) transport proteins
E) cellular proteins
Q3) Hydrogen bonding between the carbonyl group of an amino acid on one strand with the amino group of the neighboring strand leads to ______.
A) parallel \(\beta\)-pleated sheets
B) antiparallel \(\beta\)-pleated sheets
C) an \(\alpha\)-helix
D) a \(\beta\)-helix
E) either A or B
Q4) Provide the structure of the predominant form of valine at pH 10?
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Chapter 26: Lipids
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Q1) Which of the following is not a characteristic of prostaglandins?
A) five-membered cyclic ring
B) carbonyl group
C) two side chains
D) hydroxyl group
E) six-membered monocyclic ring
Q2) The reaction of triglycerides with a base is a(n) ________ reaction.
A) esterification
B) transesterification
C) saponification
D) autooxidation
E) oxidation
Q3) The rancid smell from unsaturated oils is due to ______________.
A) the reduction of the ester group
B) the oxidation of the ester group
C) the oxidation of the alkene
D) the reduction of the alkene
E) autooxidation
Q4) Provide the structure of a lecithin that would produce two stearic acid residues on hydrolysis?
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Chapter 27: Synthetic Polymers
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Q1) Which one of the following is the best classification of Nylon?
A) fibers
B) elastomers
C) plasticizers
D) thermoplastics
E) thermosetting resins
Q2) SBR (styrene-butadiene rubber) is used in the manufacturing of automobile tires.
Provide a region of the structure of this polymer.
Q3) Identify the polymer used in plumbing.
A) polytetrafluoroethylene
B) polystyrene
C) polypropylene
D) polyethylene
E) poly(vinyl chloride)
Q4) Identify the polymer that is used in rope.
A) Nylon 6
B) Teflon
C) Kevlar
D) Lexan
E) Nylon 6,6
Page 33
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