Advanced Organic Chemistry Practice
Exam
Course Introduction
Advanced Organic Chemistry delves into the mechanistic principles and synthetic strategies that underpin the structure, reactivity, and transformation of organic molecules. The course covers advanced topics such as reaction mechanisms (including pericyclic, photochemical, and organometallic processes), stereochemistry, molecular rearrangements, reactive intermediates, and contemporary synthetic methodologies. Emphasis is placed on retrosynthetic analysis, problem-solving, and the interpretation of primary literature, preparing students for research or professional practice in organic chemistry and related disciplines.
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 molecular geometry of carbon tetrachloride, CCl<sub>4</sub>, is _________ .
A) tetrahedral
B) trigonal planar
C) trigonal pyramidal
D) square planar
E) linear
Answer: A
Q2) Which molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?
A) two bonding molecular orbitals
B) only one bonding molecular orbital
C) one bonding and one antibonding molecular orbital
D) two antibonding molecular orbitals
E) only one antibonding orbital
Answer: C
Q3) Draw the Lewis structure for SOCl<sub>2</sub> and predict the hybridization state, molecular geometry and approximate bond angle around the central atom.
Answer: 11ea894b_ac4e_0c61_bba7_113eb42442a2_TB4454_00_TB4454_00 sp<sup>3</sup>, trigonal pyramidal, 107<sup>0</sup>
Page 3
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Chapter 2: Molecular Representations
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Sample Questions
Q1) Diazomethane has the molecular formula CH<sub>2</sub>N<sub>2</sub>. Draw the preferred Lewis structure for diazomethane and assign formal charges to all atoms except hydrogen.
Answer: 11ea894b_ac61_46d3_bba7_33dd416c8850_TB4454_00_TB4454_00
Q2) Draw two resonance structures for HN<sub>3</sub>.
Answer: 11ea894b_ac66_eb6c_bba7_4f79b39b0027_TB4454_00_TB4454_00
Q3) What is a resonance hybrid?
Answer: A molecule that can be represented by drawing two or more resonance structures is viewed as a resonance hybrid.
Q4) Draw the Lewis structure for (CH<sub>3</sub>)<sub>3</sub>C(CH<sub>2</sub>)<sub>2</sub>OCH(CH<sub>2</sub> CH<sub>3</sub>)<sub>2</sub>.
Answer: 11ea894b_ac55_d4ca_bba7_bfadc8d364ce_TB4454_00_TB4454_00
Q5) Draw a bond-line structure for (CH<sub>3</sub>)<sub>2</sub>N(CH<sub>2</sub>)<sub>3</sub>CH(CH<sub>3</sub>) <sub>2</sub>.
Answer: 11ea894b_ac59_cc85_bba7_53d2cdeda8c3_TB4454_00_TB4454_00
Q6) Draw the resonance hybrid of C<sub>6</sub>H<sub>6</sub>.
Answer: 11ea894b_ac68_7222_bba7_55525f20a2a7_TB4454_00_TB4454_00
Answer: 11ea894b_ac68_7223_bba7_ffc309680577_TB4454_00_TB4454_00 Page 4
Q7) Draw the resonance hybrid of CH<sub>2</sub>CHCHCHCH<sub>2</sub><sup>+</sup>.
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Chapter 3: Acids and Bases
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Sample Questions
Q1) What is the strongest base that can be used with water as a solvent?
Answer: hydroxide
Q2) CH<sub>3</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>3,</sub> is best classified as a ____.
A) Brønsted-Lowry acid
B) Lewis acid
C) Brønsted-Lowry base
D) Lewis base
E) Both C & D
Answer: E
Q3) Which of the following solvents can be used with NaNH<sub>2</sub>?
A) CH<sub>3</sub>CH<sub>2</sub>OH
B) CH<sub>3</sub>OH
C) H<sub>2</sub>O
D) Liquid NH<sub>3</sub>
Answer: D
Q4) Draw the conjugate base of CH<sub>3</sub>C\(\equiv\)CH.
Answer: 11ea894b_ac6b_0a50_bba7_bf7da56a2507_TB4454_00_TB4454_00
Q5) Draw the conjugate acid of CH<sub>3</sub>OCH<sub>3</sub>
Answer: 11ea894b_ac6a_bc2d_bba7_b95ff4ea07c8_TB4454_00_TB4454_00
Page 6
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Chapter 4: Alkanes and Cycloalkanes
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Sample Questions
Q1) Draw a chair conformation of cyclohexane showing all of the equatorial H's.
Q2) 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?
Q3) Draw the most stable chair conformer of cis-1,4-diethylcyclohexane.
Q4) What is the structure of 1-cyclopropyl-3-methylcyclopentane?
Q5) Draw the most stable chair conformer of the most stable isomer of 1,3,5-trimethylcyclohexane.
Q6) Identify the size of the hydrocarbon that is used in jet fuel.
A) C<sub>1</sub> - C<sub>4</sub>
B) C<sub>5</sub> - C<sub>12</sub>
C) C<sub>12</sub> - C<sub>18</sub>
D) C<sub>12</sub> and higher
Q7) Draw a chair conformation of ethylcyclohexane with the ethyl group axial.
Q8) Draw the most stable chair conformer of the most stable isomer of 1-ethyl-3-isopropylcyclohexane.
Q9) Draw an energy diagram for the conformational analysis of propane.
Q10) What is the structure of an isopropyl group?
Q12) What is the structure of [2.2.2]bicyclooctane? Page 7
Q11) Draw a chair conformation of methylcyclohexane.
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Page 8
Chapter 5: Stereoisomerism
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Sample Questions
Q1) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.
I. -CH<sub>2</sub>CH<sub>3</sub><sub> </sub> II. -CHCH<sub>2</sub> III. -CCH IV. -CH<sub>3</sub>
Q2) How many stereoisomers are possible for 2,3-dimethylbutane?
Q3) What is the percentage of the R enantiomer in a sample of limonene that has a specific rotation of 38, given that the specific rotation of (S)-limonene is 116?
Q4) Draw all the isomers with molecular formula C<sub>4</sub>H<sub>6</sub>.
Q5) What is the % ee of a sample of carvone that exhibits a specific rotation of 20, given that the specific rotation of (R)-carvone is 61?
Q6) Stereoisomers that result from the hindered rotation of a single bond are called
Q7) 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
Page 9
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Chapter 6: Chemical Reactivity and Mechanisms
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Sample Questions
Q1) Identify the electrophilic site in the following molecule, CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>2</sub>CH<sub>3</sub>.
A) H
B) N
C) CH<sub>2</sub>
D) CH<sub>3</sub>
E) there is no electrophilic site
Q2) What is an intermediate?
A) A local maximum on the energy diagram.
B) A point on the reaction pathway that has a discrete minima.
C) A point half-way between the starting materials and products.
D) The highest energy compound on an energy diagram.
Q3) Draw an energy diagram for a concerted exothermic reaction.
Q4) Does a reaction with a H of 14 kJ/mol and a S of 150 J/mol·K at 298 K favor reactants or products?
Q5) What is the effect of a catalyst on a reaction?
A) It increases the rate.
B) It decreases the entropy.
C) It changes the equilibrium.
D) It makes the products more stable.
Page 10
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Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination
Reactions
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Sample Questions
Q1) 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
Q2) Identify the type of elimination in an E2 mechanism.
A) alpha elimination
B) beta elimination
C) gamma elimination
D) delta elimination
E) omega elimination
Q3) Describe a strong nucleophile.
A) an anion
B) a cation
C) a radical
D) a neutral compound
Q4) Draw the structure of 3-methylcyclopentene.
Q6) Draw the structure of 2,3-dimethyl-1-pentene. Page 11
Q5) Provide the structure for 1-chloro-4-isopropylheptane.
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Chapter 8: Addition Reactions of Alkenes
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Sample Questions
Q1) What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?
A) 1-chloro-2-methylbutane
B) 1-chloro-3-methylbutane
C) 2-chloro-2-methylbutane
D) 2-chloro-3-methylbutane
E) 1-chloropentane
Q2) Alkenes are found in ________, which are used by living organisms to trigger specific behavioral responses in other members of the same species.
Q3) How many moles of hydrogen (H<sub>2</sub>) are consumed in the catalytic reduction of 1 mole of 1,3-dibromocyclohexa-1,4-diene?
A) 1
B) 2
C) 3
D) 4
E) None of the above
Q4) The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is named after which chemist?
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Chapter 9: Alkynes
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Sample Questions
Q1) What reagent(s) are required to prepare trans-2-heptene from 2-heptyne?
Q2) Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.
A) cis-3-hexene
B) trans-2-hexene
C) 3-hexyne
D) 2-hexyne
E) cis-2-hexene
Q3) The sigma bond of an alkyne is formed from the overlap of which two orbitals?
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
Q4) What is the IUPAC name for diisobutylacetylene?
A) diisopropylbutyne
B) 2,7-dimethyl-4-octyne
C) 3,6-dimethyl-4-octyne
D) 2,5-diethyl-3-hexyne
E) 2,2,5,5-tetramethyl-3-hexyne
Page 14
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Chapter 10: Radical Reactions
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Sample Questions
Q1) 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.
Q2) Which of the following correctly describes the nature of the transition state of the rate-determining step of the free-radical bromination of methane?
A) the transition state resembles the reactants more than the products
B) the transition state resembles the products more than the reactants
C) the transition state equally resembles products and reactants
Q3) Which of the following is most reactive towards chlorination?
A) methane
B) chloromethane
C) dichloromethane
D) chloroform
E) ethane
Q4) Which monomer is used for the synthesis of Teflon?
A) 1,1-difluoroethene
B) 1,1,2,2-tetrafluoropropene
C) 1,1,2,2-tetrafluoroethene
D) tetrafluoromethane
Q5) Propose a synthesis of 2-butyn-1-ol from propane.
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Chapter 11: Synthesis
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Sample Questions
Q1) Taxol is a powerful _____.
A) laxative
B) pain-killer
C) birth-control pill
D) anti-cancer drug
E) hallucinogen
Q2) Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.
A) hept-1-en-4-yne
B) hept-6-en-3-yne
C) hept-3-en-6-yne
D) hept-4-en-1-yne
E) hept-2-en-4-yne
Q3) Devise a synthetic route to convert 5-methyl-1-hexene into 5-methylhexanal.
Q4) Most synthesis problems will have _________ (one, many) correct answers.
Q5) Propose a synthesis of propanoic acid from acetylene.
Q6) Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.
Q7) Devise a synthetic route to prepare 1,3-dibromopropan-2-ol from propene.
Q9) Devise a synthetic route to prepare 1,7-heptanediol from propene. Page 16
Q8) Devise a synthetic route to convert ethylene into PVC (polyvinyl chloride).
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Chapter 12: Alcohols and Phenols
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Sample Questions
Q1) 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.
Q2) Identify rubbing alcohol.
A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol
Q3) The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene goes via a(n) _____.
A) S<sub>N</sub>1 mechanism
B) S<sub>N</sub>2 mechanism
C) E1 mechanism
D) E2 mechanism
E) None of these.
Q4) Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol.
Q5) Give the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol.
Q6) Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.
Page 18
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Chapter 13: Ethers and Epoxides; Thiols and Sulfides
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Sample Questions
Q1) What is the correct structure for phenylthiol?
Q2) 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
Q3) Which one of the following reactions would produce t-butyl methyl ether in high yield?
A) CH<sub>3</sub>ONa + (CH<sub>3</sub>)<sub>3</sub>CBr
B) CH<sub>3</sub>OH + (CH<sub>3</sub>)<sub>3</sub>COH in the presence of H<sub>2</sub>SO<sub>4</sub> at 140°C
C) CH<sub>3</sub>Cl + (CH<sub>3</sub>)<sub>3</sub>CBr in the presence of NaOH
D) (CH<sub>3</sub>)<sub>3</sub>CONa + CH<sub>3</sub>Br
Q4) What type of molecular interactions do ethers have?
A) dipole-dipole interactions
B) ion-dipole interactions
C) ion-ion interactions
D) London dispersion forces
E) hydrogen bonding
Page 19
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Chapter 14: Infrared Spectroscopy and Mass Spectrometry
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Sample Questions
Q1) Calculate the degree of unsaturation for C<sub>14</sub>H<sub>14</sub>N<sub>2</sub>O.
A) 4
B) 6
C) 8
D) 10
E) 9
Q2) For which of the following compounds will the (M+2)<sup>+</sup> peak intensity be around one third the intensity of the molecular ion peak?
A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br
B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cl
D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
E) none of these
Q3) Propose all possible structures for a compound with molecular formula C<sub>4</sub>H<sub>9</sub>N that shows two medium absorptions at 3400 cm<sup>-1</sup> and no absorption in the range of 1600 - 1800 cm<sup>-1</sup> in its IR spectrum.
Q4) Warmer objects emit more __________ radiation.
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Chapter 15: Nuclear Magnetic Resonance Spectroscopy
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Sample Questions
Q1) The <sup> ADVANCE \u 2</sup><sup>1</sup> ADVANCE \d 2H NMR spectrum of 1-propanol displays a singlet for the OH proton instead of a triplet. Explain why.
Q2) Which of the following nuclei cannot be analyzed by an NMR spectrometer?
A) nucleus with odd number of protons & odd number of neutrons
B) nucleus with odd number of protons &even number of neutrons
C) nucleus with even number of protons & odd number of neutrons
D) nucleus with even number of protons & even number of neutrons
E) none of these
Q3) Aromatic protons produce signals in the range of 7 - 8 ppm, due to the _________effect of \(\pi\) electrons
A) diamagnetic anisotropy
B) paramagnetic anisotropy
C) diamagnetic isotropy
D) paramagnetic isotropy
E) none of these
Q4) Predict the multiplicity of each signal in the expected <sup>1</sup>H NMR spectrum of 2,3-dimethyl-2-pentanol.
Q5) Draw a structure, with a formula of C<sub>5</sub>H<sub>13</sub>N, which has an integration of 9H, 3H, 1H.
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Chapter 16: Conjugated Pi Systems and Pericyclic Reactions
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Sample Questions
Q1) Which is the most energetically favorable UV transition for 1,3-butadiene?
A) (n \(\to\) \(\sigma\)*)
B) (n \(\to\) \(\pi\)*)
C) (\(\pi\)<sub>2 </sub> \(\to\) \(\pi\)<sub>3</sub>*)
D) (\(\sigma\) \(\to\) \(\sigma\)*)
E)(\(\pi\)<sub>1 </sub> \(\to\) \(\pi\)<sub>4</sub>*)
Q2) Which one of the following dienes is least stable?
A) CH<sub>3</sub>CH=CHCH=CHCH<sub>3</sub>
B) CH<sub>3</sub>CH=CHCH<sub>2</sub>CH=CH<sub>2</sub>
C) CH<sub>2</sub>=CHCH<sub>2</sub>CH<sub>2</sub>CH=CH<sub>2</sub>
D) CH<sub>2</sub>=CHCH(CH<sub>3</sub>)CH=CH<sub>2</sub>
E) CH<sub>3</sub>CH=C=CHCH<sub>2</sub>CH<sub>3</sub>
Q3) Identify the conjugated diene(s).
A. 4-methyl-1,3-heptadiene
B. 3-methyl-1,5-heptadiene
C. 2-methyl-2,4-heptadiene
D. 4-methyl-1,4-heptadiene
E. 5-methyl-2,3-heptadiene
Q4) The addition of a _____________ bond improves the elasticity in synthetic rubber.
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Chapter 17: Aromatic Compounds
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Sample Questions
Q1) Give the common name for toluene.
A) hydroxybenzene
B) aminobenzene
C) methylbenzene
D) ethylbenzene
E) methoxybenzene
Q2) Identify the number of \(\pi\) electrons present in an aromatic compound.
A) 4n + 2
B) 2n + 2
C) 4n
D) 2n
E) 3n
Q3) Identify the aromatic hydrocarbon with the highest stabilization energy.
A) phenanthrene
B) benzene
C) naphthalene
D) anthracene
Q4) Provide the reagents necessary to convert ethylbenzene to styrene.
Q5) What is the structure for styrene?
Q6) What is the structure for 3-isobutyl-5-isopropylaniline?
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Chapter 18: Aromatic Substitution Reactions
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Q1) In a Clemmensen reduction, an aryl ketone is reduced to _____________.
A) an aryl aldehyde
B) an aryl alkane
C) an aryl carboxylic acid
D) an aryl ester
E) an aryl anhydride
Q2) Which of the following substituents will direct the incoming group to the ortho/para position during electrophilic aromatic substitution?
A) -CH<sub>2</sub>CH<sub>3</sub>
B) -CF<sub>3</sub>
C) -OCH<sub>3</sub>
D) -COOCH<sub>3</sub>
E) both A and C
Q3) Draw all of the resonance structures of the sigma complex which is formed when benzene reacts with an electrophile (E<sup>+</sup>).
Q4) A nitro group ___________ the benzene ring to make it __________ reactive than benzene.
Q5) A halogen ___________ the benzene ring; the ring is __________ reactive than benzene.
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Chapter 19: Aldehydes and Ketones
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Sample Questions
Q1) Using 1-propanol as your only source of carbon, and using any other reagents as appropriate, write a complete stepwise synthesis for 3-hexanone.
Q2) Provide the structure for (S)-3-chlorocyclohexanone.
Q3) The <sup>13</sup>C NMR spectrum of a compound with formula C<sub>7</sub>H<sub>14</sub>O shows five signals. Which one of the following is a possible structure for this compound?
A) 2-heptanone
B) 3-heptanone
C) 2,2-dimethyl-3-pentanone
D) 2,4-dimethyl-3-pentanone
E) none of these
Q4) What is the correct order of the migration rate for the following groups in the Baeyer-Villiger oxidation reaction?
A) phenyl > methyl > t-butyl > H
B) phenyl > t-butyl > methyl > H
C) H > phenyl > methyl > t-butyl
D) H > t-butyl > phenyl > methyl
E) methyl > t-butyl > phenyl > H
Q5) Provide the structure for 2,3-dimethyl-2-octen-4-one.
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Chapter 20: Carboxylic Acids and Their Derivatives
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Sample Questions
Q1) A compound with molecular formula C<sub>8</sub>H<sub>14</sub>O<sub>3</sub> exhibits a triplet at \(\delta\) 1.0 (6H), a sextet at \(\delta\) 1.6 (4H) and a triplet at \(\delta\) 2.2 (4H) in its <sup>1</sup>H NMR spectrum. Its IR spectrum shows two strong absorption bands near 1850 and 1750 cm<sup>-1</sup>. What is the structure for this compound?
Q2) Provide the structure for (3S,4S)-3-hydroxy-4-phenylnonanoic acid.
Q3) Which one of the following is the strongest acid? Explain your choice.
A)2,3-dimethylheptanoic acid
B)3,3-dichlorohexanoic acid
C)4-bromo-3-iodohexanoic acid
D)4-bromo-3-chloroheptanoic acid
E)4-bromo-2-fluorohexanoic acid
Q4) Which one of the following is the weakest acid?
A) benzoic acid
B) 4-nitrobenzoic acid
C) 4-ethylbenzoic acid
D) 4-chlorobenzoic acid
E) 4-hydroxybenzoic acid
Q5) Provide the structure for cyclopentanecarbonyl chloride.
Q6) Provide the structure for benzoic ethanoic anhydride.
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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 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
Q2) Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.
Q3) Which cannot be used in a Claisen condensation?
A) two esters, both without alpha hydrogens
B) one ester with an alpha hydrogen and one ester without an alpha hydrogen
C) two esters, both with alpha hydrogens
D) all of these
E) none of these
Q4) Provide the structure of the enol when 3,3,6-trimethyl-4-heptanone is treated with acid.
Q5) Explain why CH<sub>3</sub>ONa should not be used for Claisen condensation of ethylbutanoate.
Page 27
Q6) An intermolecular Claisen condensation is called a _____________.
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Chapter 22: Amines
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Sample Questions
Q1) Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.
Q2) The ________ reaction is used to prepare primary amines by using potassium phthalimide. This reaction proceeds by a ________ mechanism.
Q3) What is the structure for N-ethylbenzylamine?
Q4) Which of the following is a quaternary ammonium salt?
A)
CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>3</sub><sup >+</sup> Cl<sup>-</sup>
B) (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>NH<sub>2</sub><sup>+</sup> Cl<sup>-</sup>
C) (CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>NH<sup>+</sup> Cl<sup>-</sup>
D) (CH<sub>3</sub>CH<sub>2</sub>)<sub>4</sub>N<sup>+ </sup>Cl<sup>-</sup>
E) (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>NCH<sub>3</sub>
Q5) Identify the strongest base.
A) 4-chloroaniline
B) 4-nitroaniline
C) 4-aminobenzonitrile
D) aniline
E) 4-aminoanisole
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Chapter 23: Introduction to Organometallic Compounds
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Sample Questions
Q1) Identify the product when a nitrile reacts with one equivalent of a Grignard reagent.
A) primary alcohol
B) secondary alcohol
C) tertiary alcohol
D) carboxylic acid
E) ketone
Q2) Which of the following is a Simmons-Smith cyclopropanation?
A) R-X + Zn
B) R<sub>2</sub>C=CR<sub>2 </sub> + CH<sub>2</sub>I<sub>2</sub> + Zn-Cu
C) CHCl<sub>3</sub> + NaOH
D) R<sub>2</sub>C=CHI + (CH<sub>3</sub>)<sub>2</sub>CuLi
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) Explain why the solvent for a Grignard reaction must be free of water.
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Chapter 24: Carbohydrates
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Q1) Which of the following pairs of D-aldohexoses would produce the same product when subjected to Wohl degradation?
A) D-glucose and D-galactose
B) D-mannose and D-galactose
C) D-glucose and D-gulose
D) D-allose and D-altrose
E) D-glucose and D-allose
Q2) Anomers of D-fructofuranose differ in stereochemistry at ____ carbon.
A) C1
B) C2
C) C3
D) C4
E) C5
Q3) Polysaccharides are made by joining ________together.
A) disaccharides
B) trisaccharides
C) polysaccharides
D) monosaccharides
E) all of these
Q4) Predict the product(s) when maltose is treated with CH<sub>3</sub>OH/HCl.
Page 30
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Chapter 25: Amino Acids, Peptides, and Proteins
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Q1) Which of the following tripeptides is formed when alanine is treated with (BoC)<sub>2</sub>O and proline is treated with benzyl alcohol/acid first and the resulting intermediates are reacted in the presence of DCC followed by treatment with aqueous NaOH. The dipeptide is then reacted with the benzyl ester of leucine in the presence of DCC followed by treatment with trifluoroacetic acid and then aqueous NaOH?
A) Ala-Pro-Leu
B) Pro-Ala-Leu
C) Leu-Ala-Pro
D) Pro-Leu-Ala
E) all of these
Q2) Which of the following fragments are formed when the following peptide is cleaved using chymotrypsin? Gly-Lys-Cys-Phe-Ile-Val-Tyr-Ala-Ser
A) Gly-Lys-Cys, Phe-Ile-Val, Tyr-Ala-Ser
B) Gly-Lys-Cys-Phe, Ile-Val-Tyr, Ala-Ser
C) Gly-Lys-Cys-Phe, Ile-Val, Tyr-Ala-Ser
D) Gly-Lys-Cys, Phe, Ile-Val-Tyr, Ala-Ser
E) Gly-Lys, Cys-Phe, Ile-Val-Tyr-Ala-Ser
Q3) Provide the reagents necessary to prepare phenylalanine using a Strecker synthesis.
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Page 31
Chapter 26: Lipids
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Sample Questions
Q1) Provide the structure of an optically active triglyceride that produced two myristic acid residues and an oleic acid residue when heated in the presence of an acid.
Q2) Identify the substance that can be made from heating animal fat with wood ashes, which contain alkaline substances.
A) detergent
B) soap
C) cooking oil
D) kerosene
E) biodiesel
Q3) A lipid bilayer is formed by the self assembly of _________.
A) triglycerides
B) saturated fatty acids
C) phosphoglycerides
D) unsaturated fatty acids
E) alcohols
Q4) Provide the structure of a lecithin that would produce two stearic acid residues on hydrolysis?
Q5) Predict the product when testosterone is treated with PCC.
Q6) Explain why fatty acids cannot form a bilayer.
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Chapter 27: Synthetic Polymers
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Q1) Which of the following types of polyethylene is used to make tupperware?
A) HDPE
B) LDPE
C) MDPE
D) A and C
E) none of these
Q2) Draw a possible segment of syndiotactic polyacrylonitrile.
Q3) Give the monomers to form Lexan.
Q4) Which of the following is used as an initiator in radical polymerization?
A) BF<sub>3</sub>, H<sub>2</sub>O
B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Li
C) ROOR
D) NaOH
E) H<sub>2</sub>O
Q5) Which one of the following is the best classification of Nylon?
A) fibers
B) elastomers
C) plasticizers
D) thermoplastics
E) thermosetting resins
Page 33
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