

Advanced Organic Chemistry
Exam Solutions

Course Introduction
Advanced Organic Chemistry delves deeply into the mechanistic and theoretical aspects of organic reactions, building upon foundational organic chemistry concepts. Students will explore topics such as reaction mechanisms, stereochemistry, molecular orbital theory, reactive intermediates, catalysis, and advanced synthetic strategies. Emphasis is placed on understanding reaction pathways, predicting chemical reactivity, and utilizing modern analytical techniques. This course also incorporates recent developments in organic synthesis and challenges learners to solve complex problems encountered in laboratory and research settings, preparing them for further studies or careers in chemistry-related fields.
Recommended Textbook
Organic Chemistry 4th Edition by Janice Gorzynski
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31 Chapters
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Page 2
Chapter 1: Structure and Bonding
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Sample Questions
Q1) What is the order of decreasing bond length for a C-C bond comprised of the following molecular orbitals? \[\begin{array} { c c c }
s p ^ { 3 } - s p ^ { 3 } & s p ^ { 2 } - s p ^ { 2 } & s p - s p \\ \text { I } & \text { II } & \text { III }
\end{array}\]
A) I > III > II
B) I > II > III
C) III > II > I
D) II > III > I
Answer: B
Q2) Which of the following statements about bonding is true?
A) Covalent bonds result from the transfer of electrons from one element to another.
B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.
C) Ionic bonds result from the sharing of electrons between two non-metals.
D) Covalent bonds result from the sharing of electrons between two metals.
Answer: B
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3

Chapter 2: Acids and Bases
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Sample Questions
Q1) Which of the following statements is a correct definition for a Brønsted-Lowry acid?
A) Proton acceptor
B) Electron pair donor
C) Electron pair acceptor
D) Proton donor
Answer: D
Q2) Which of the following species is the conjugate base of the hydronium ion, H<sub>3</sub>O<sup>+</sup>?
A) H<sub>3</sub>O
B) H<sub>2</sub>O<sup>-</sup>
C) H<sub>2</sub>O
D) HO<sup>-</sup>
Answer: C
Q3) Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A) CH<sub>3</sub>OH
B) H<sub>2</sub>O
C) CH<sub>3</sub>COOH
D) BF<sub>3</sub>
Answer: D
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Page 4

Chapter 3: Introduction to Organic Molecules and Functional Groups
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Sample Questions
Q1) Which of the following statements about the solubility of organic compounds in H<sub>2</sub>O is true?
A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic.
B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic.
C) The polar part of a molecule that can hydrogen bond to water is said to be hydrophobic.
D) For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has \(\ge\) 5 carbons.
Answer: B
Q2) Why do \(\pi\) bonds confer reactivity on a particular molecule?
A) Because \(\pi\) bonds are difficult to break in chemical reactions.
B) Because \(\pi\) bonds make a molecule an acid.
C) Because \(\pi\) bonds are easily broken in chemical reactions.
D) Because \(\pi\) bonds make a molecule an electrophile.
Answer: C
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Page 5

Chapter 4: Alkanes
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Sample Questions
Q1) Which of the following statements about alkanes is not true?
A) Alkanes are aliphatic hydrocarbons.
B) Alkanes contain only C-C and C-H \(\sigma\) bonds.
C) Alkanes are acyclic or cyclic.
D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons.
Q2) Which of the following compounds has only primary, secondary and quaternary carbon atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,2,3-Trimethylpentane
Q3) Which of the following compounds has primary, secondary and tertiary hydrogen atoms?
A) Pentane
B) Hexane
C) 2-Methylpentane
D) 2,2-Dimethylpentane
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Chapter 5: Stereochemistry
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Sample Questions
Q1) Which of the following molecules are chiral? I. 2-Chlorobutane
II) 3-Bromopentane
III) 1-Bromo-2-methylpropene
IV) 2-Bromo-3-methylbutane
A) I, II
B) I, IV
C) II, III
D) III, IV
Q2) Which of the following is the definition for a pair of diastereomers?
A) A pair of stereoisomers with stereogenic centers which is not chiral.
B) A pair of stereoisomers that are superimposable mirror images of each other.
C) A pair of stereoisomers that are not superimposable mirror images of each other.
D) A pair of stereoisomers that are not mirror images of each other.
Q3) How much of the R enantiomer is present in 10 g of a mixture which has an enantiomeric excess of 30% of the S isomer?
A) 3.0 g
B) 3.5 g
C) 6.5 g
D) 7.0 g
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Page 7
Chapter 6: Understanding Organic Reactions
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Sample Questions
Q1) Which of the following statements about enzymes is true?
A) Enzymes increase the activation energy for a reaction.
B) Enzymes decrease the equilibrium constant.
C) Enzymes shift the equilibrium to favor the product.
D) Enzymes lower the transition state for the rate-determining step.
Q2) Which of the following statements about elimination reactions is true?
A) Two \(\sigma\) bonds are broken.
B) Two \(\sigma\) bonds are formed.
C) Two \(\pi\) bonds are broken.
D) Two \(\pi\) bonds are formed.
Q3) Which of the following reaction quantities will have an effect on reaction rate?
A) "\(\Delta\)G°"
B) "\(\Delta\)H°"
C) "K<sub>eq</sub>"
D) "E<sub>a</sub>"
Q4) Which of the K<sub>eq</sub> corresponds to the highest value of \(\Delta\)G°?
A) K<sub>eq</sub> = 10<sup>-1</sup>
B) K<sub>eq</sub> = 10<sup>-2</sup>
C) K<sub>eq</sub> = 10<sup>-3</sup>
D) K<sub>eq</sub> = 10<sup>-5</sup>

Page 8
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Chapter 7: Alkyl Halides and Nucleophilic Substitution
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Sample Questions
Q1) The reaction of tert-butyl bromide, (CH<sub>3</sub>)<sub>3</sub>CBr, with ethanol affords the substitution product tert-butyl ethyl ether, (CH<sub>3</sub>)<sub>3</sub>COCH<sub>2</sub>CH<sub>3</sub>, in acidic conditions. What would happen to the rate of the reaction if the concentration of ethanol was doubled?
A) The rate remains the same.
B) The rate decreases by a factor of 2.
C) The rate increases by a factor of 2.
D) The rate increases by a factor of 4.
Q2) Which of the following alkyl halides undergoes the fastest S<sub>N</sub>2 reaction with sodium hydroxide?
A) 1-Iodobutane
B) 1-Chlorobutane
C) 1-Fluorobutane
D) 1-Bromobutane
Q3) Which of the following statements is not true?
A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide.
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases.
C) Sterically hindered bases are also called nonnucleophilic bases.
D) Steric hindrance decreases basicity but not nucleophilicity.
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Chapter 8: Alkyl Halides and Elimination Reactions
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Q1) How many different E2 products can form from the dehydrohalogenation of 2-bromobutane?
A) 1
B) 2
C) 3
D) 4
Q2) Which of the following is the most reactive substrate in an E2 reaction? \(\mathrm { CH } _ { 3 } \mathrm { Br } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } \quad \mathrm { CH } _ { 3 } \mathrm { CH } \left( \mathrm { Br } ^ { 2 } \right) \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 } \quad \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CBr }\)
I
\(\quad\quad\quad\quad\quad\quad\quad\)II\(\quad\quad\quad\quad\quad\ quad\quad\quad\quad\quad\)III\(\quad\quad\quad\quad\quad\quad\quad\qu ad\)IV
A) I
B) II
C) III
D) IV
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Page 10

Chapter 9: Alcohols, Ethers and Epoxides
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Q1) What are the major products obtained upon treatment of methyl phenyl ether with excess HBr?
A) Phenol and bromomethane
B) Phenol and methanol
C) Bromobenzene and bromomethane
D) Bromobenzene and methanol
Q2) Which of the following statements about the reaction of ethers with strong acids is true?
A) HCl, HBr and HI can all be used.
B) The mechanism of ether cleavage is S<sub>N</sub>1 only.
C) The mechanism of ether cleavage is S<sub>N</sub>2 only.
D) The mechanism of ether cleavage is S<sub>N</sub>1 and S<sub>N</sub>2.
Q3) Which of the following statements about a crown ether-cation complex is not true?
A) It is a host-guest complex.
B) The crown ether is the guest and the cation is the host.
C) The crown ether is the host and the cation is the guest.
D) The host-guest complex is soluble in nonpolar solvents.
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Chapter 10: Alkenes
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Sample Questions
Q1) Which of the following statements about hydroboration/oxidation of alkenes is true?
A) In hydroboration, the boron atom bonds to the more substituted carbon.
B) Hydroboration occurs with anti addition.
C) Oxidation occurs with retention of configuration.
D) 9-BBN does not undergo hydroboration in the same manner as BH<sub>3</sub>.
Q2) Which of the following reactions of alkenes takes place with anti stereochemistry only?
A) Addition of HBr
B) Addition of H<sub>2</sub>O in the presence of H<sub>2</sub>SO<sub>4</sub>
C) Addition of BH<sub>3</sub> followed by H<sub>2</sub>O<sub>2</sub>/HO<sup>-</sup>
D) Addition of Br<sub>2</sub>
Q3) Markovnikov addition of HBr to CH<sub>3</sub>CH=CH<sub>2</sub> involves which of the following?
A) Initial attack by bromide anion (Br<sup>-</sup>).
B) Initial attack by bromine radical (Br ).
C) Formation of a primary carbocation.
D) Formation of a secondary carbocation.
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Page 12
Chapter 11: Alkynes
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Q1) Which of the following statements about alkynes is not true?
A) Alkynes undergo many addition reactions.
B) Alkynes are more polarizable than alkenes.
C) Both \(\pi\) bonds of a C-C triple bond are weaker than a C-C \(\sigma\) bond.
D) The electrons in the \(\pi\) bonds of alkynes are more tightly held than those of alkenes.
Q2) Which of the following about the physical properties of alkynes is not true?
A) Alkynes have low melting and boiling points.
B) Melting and boiling points increase as the number of carbons increases.
C) Alkynes are soluble in organic solvents.
D) Alkynes are soluble in water.
Q3) In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is:
A) The Csp-H1s bond of 1-butyne.
B) The C-C triple bond of 1-butyne.
C) The H atom in HBr.
D) The Br ion.
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Page 13

Chapter 12: Oxidation and Reduction
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Sample Questions
Q1) What happens to the carbon atom in the transformation of chloromethane to methyllithium? CH<sub>3</sub>Cl + 2Li \(\to\) CH<sub>3</sub>Li + LiCl
A) Oxidized
B) Reduced
C) Oxidized and Reduced
D) Neither oxidized nor reduced
Q2) A compound X of molecular formula C<sub>8</sub>H<sub>12</sub> with no triple bonds reacts with one equivalent of H<sub>2</sub> to give a new compound having molecular formula C<sub>8</sub>H<sub>14</sub>. What can be inferred about the structure of compound X?
A) Compound X has 3 rings.
B) Compound X has 3 \(\pi\) bonds.
C) Compound X has 1 ring and 2 \(\pi\) bonds.
D) Compound X has 2 rings and 1 \(\pi\) bond.
Q3) Which of the following statements about oxidation and reduction is not true?
A) The conversion of an alkyne to an alkene is reduction.
B) The conversion of an alkene to an alkane is reduction.
C) Oxidation results in a decrease in the number of C-H bonds.
D) Reduction results in an increase in the number of C-Z bonds.
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Page 14
Chapter 13: Mass Spectrometry and Infrared Spectroscopy
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Sample Questions
Q1) Which of the following statement(s) is (are) true about a compound that has a molecular ion peak in its mass spectrum at mass 69, and shows a prominent peak in its IR spectrum at 2250 cm<sup>-1</sup>?
A) The compound has a molecular mass of 70.
B) The compound contains a C=O group.
C) The compound contains a cyano or alkyne group.
D) Both (The compound has a molecular mass of 70) and (The compound contains a C=O group) are true statements.
E) Both (The compound has a molecular mass of 70) and (The compound contains a cyano or alkyne group) are true statements.
Q2) What type(s) of molecular motion is (are) observed using infrared spectroscopy?
A) Stretching and bending
B) Rotation and excitation
C) Spin flipping
D) Fragmentation
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15

Chapter 14: Nuclear Magnetic Resonance Spectroscopy
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Sample Questions
Q1) Which of the following spectroscopy methods does not involve the interaction of organic molecules with electromagnetic radiation?
A) Nuclear Magnetic Resonance
B) Infrared spectroscopy
C) Mass spectroscopy
D) Ultraviolet spectroscopy
Q2) Which of the following statements about <sup>13</sup>C NMR is not true?
A) "In <sup>13</sup>C proton-decoupled NMR spectra, all peaks are singlets."
B) "<sup>13</sup>C NMR spectra display peaks for only carbons that bear hydrogen atoms."
C) "<sup>13</sup>C NMR chemical shifts occur over a greater range than <sup>1</sup>H NMR chemical shifts."
D) "<sup>13</sup>C NMR easily differentiates between the different hybridized carbons (sp<sup>3</sup>, sp<sup>2</sup> and sp hybridized carbons)."
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Chapter 15: Radical Reactions
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Q1) How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>3</sub> with Cl<sub>2</sub> and hv?
A) 2
B) 3
C) 4
D) 5
Q2) Which of the following statements about carbon radicals is not true?
A) Carbon radicals are classified as primary, secondary, tertiary, or quaternary.
B) A carbon radical is sp<sup>2</sup> hybridized.
C) The geometry of a carbon radical is trigonal planar.
D) The unhybridized p orbital in a carbon radical contains the unpaired electron.
Q3) Which of the following statements about bromination is true?
A) The rate-determining step in bromination is exothermic.
B) Both radicals are formed.
C) A mixture of products results.
D) A single radical halogenation product predominates.
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Chapter 16: Conjugation, Resonance, and Dienes
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Q1) Which of the following statements about the Diels-Alder reaction is true?
A) The diene can react only when it adopts the s-trans conformation.
B) Electron-withdrawing substituents in the diene increase reaction rate.
C) Electron-donating substituents in the dienophile increase the reaction rate.
D) The stereochemistry of the dienophile is retained in the product.
Q2) Which of the following electronic transitions is common in the UV spectrum of 1,3-butadiene?
A) "\(\sigma\) \(\to\) \(\pi\)"
B) "\(\sigma\) \(\to\) \(\pi\)*"
C) "n \(\to\) \(\pi\)*"
D) "\(\pi\) \(\to\) \(\pi\)*"
Q3) What is the kinetic product obtained from the addition of 1 equivalent of HBr to 1,3-butadiene?
A) 3-Bromo-1-butene
B) 1-Bromo-2-butene
C) 2-Bromo-2-butene
D) 2-Bromo-1-butene
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Chapter 17: Benzene and Aromatic Compounds
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Q1) Which of the following is not one of the Hückel's criteria for aromaticity?
A) The molecule must be cyclic.
B) The molecule must be planar.
C) The molecule must be completely conjugated.
D) The molecule must have 4n pi electrons.
Q2) Where do the protons in benzene appear in the <sup>1</sup>H NMR spectrum?
A) Around 1600 cm<sup>-1</sup>
B) Around 120 ppm
C) Around 0 ppm
D) Around 7 ppm
Q3) Which of the following is not a criterion for antiaromaticity?
A) The molecule must be cyclic.
B) The molecule must have (4n + 2) pi electrons.
C) The molecule must be planar.
D) The molecule must be completely conjugated.
Q4) Which of the following statements about benzene is true?
A) Benzene is a saturated hydrocarbon.
B) Benzene undergoes addition reactions.
C) Benzene has five degrees of unsaturation.
D) Benzene undergoes substitution reactions.
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Chapter 18: Electrophilic Aromatic Substitution
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Q1) Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first. \[\begin{array} { c c c c }
- \mathrm { COOH } & - \mathrm { CHO } & - \mathrm { SO } _ { 3 } \mathrm { H } &\mathrm { NO } _ { 2 } \\
\text { I } & \text { II } & \text { III } & \text { IV } \end{array}\]
A) I < II < III < IV
B) II < III < IV < I
C) II < I < III < IV
D) IV < III < I < II
Q2) Which of the following substituents is a meta director?
A) "- N(CH<sub>3</sub>)<sub>2</sub>"
B) "- OCH<sub>3</sub>"
C) "- NHCOCH<sub>3</sub>"
D) "- SO<sub>3</sub>H"
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Page 20

Chapter 19: Carboxylic Acids and the Acidity of the O-H
Bond
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Q1) Which of the following is the most polar organic compound?
A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
B) CH<sub>3</sub>CH<sub>2</sub>CHO
C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH
D) CH<sub>3</sub>COOH
Q2) What is the hybridization of the carbon atom in a carboxy group?
A) sp
B) sp<sup>2</sup>
C) sp<sup>3</sup>
D) p
Q3) What is the overall charge of the amino acid, alanine, at pH = 7?
A) + 1
B) - 1
C) No overall charge
D) + 2
Q4) What is the overall charge of the amino acid, alanine, at pH = 2?
A) + 1
B) - 1
C) No overall charge
D) + 2
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Chapter 20: Introduction to Carbonyl Chemistry;
Organometallic Reagents; Oxidation and Reduction
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Q1) Which of the following terms explain why aldehydes are more reactive than ketones?
A) Electronegativity and resonance
B) Hybridization and resonance
C) Electronegativity and hybridization
D) Sterics and electronics
Q2) What reagent would be used to reduce an amide to an amine?
A) NaBH<sub>4</sub>
B) LiAlH(OtBu)<sub>3</sub>
C) LiAlH<sub>4</sub>
D) FeCl<sub>3</sub>
Q3) Which reagent can be used to reduce an acid chloride to an aldehyde?
A) NaBH<sub>4</sub>
B) LiAlH(OtBu)<sub>3</sub>
C) LiAlH<sub>4</sub>
D) FeCl<sub>3</sub>
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Chapter 21: Aldehydes and Ketones Nucleophilic Addition
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Q1) Which of the following statements about carbohydrates is not true?
A) Carbohydrates are sugars and starches.
B) Carbohydrates often contain acetals and hemiacetals.
C) In solution, glucose is in the cyclic acetal form only.
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.
Q2) Why are strongly acidic conditions not used in the formation of enamines and imines?
A) The carbonyl will be protonated.
B) The amine will be completely protonated.
C) The product is not stable to strong acid.
D) An enol will be formed.
Q3) Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde?
A) A ketone has no carbonyl stretch at 1720 cm<sup>-1</sup>.
B) An aldehyde has a carbonyl stretch at 1820 cm<sup>-1</sup>.
C) An aldehyde has two C-H stretches between 2700-2850 cm<sup>-1</sup>.
D) A ketone has no C-H stretches.
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Chapter 22: Carboxylic Acids and Derivatives
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Q1) Where is the carbonyl absorption found in the IR spectrum of a simple ester?
A) 2.5 ppm
B) 2250 cm<sup>-1</sup>
C) 3800 cm<sup>-1</sup>
D) 1740 cm<sup>-1</sup>
Q2) All of the following contain sp<sup>2</sup> hybridized atoms in their functional group except
A) a carboxylic acid
B) a nitrile
C) an aldehyde
D) an anhydride
Q3) How can you convert a carboxylic acid into an ester?
A) Heat with an alcohol and catalytic acid
B) Deprotonate with a base and react with an alcohol
C) Deprotonate with a base and react with an alkyl halide
D) Both (a) heat with an alcohol and catalytic acid and (c) deprotonate with a base and react with an alkyl halide
E) Both (a) heat with an alcohol and catalytic acid and (b) deprotonate with a base and react with an alcohol
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Page 24

Chapter 23: Substitution Reactions of Carbonyl
Compounds at the Alpha-Carbon
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Q1) If you want to form a kinetic enolate, you want to:
A) Use a strong, non-nucleophilic base such as LDA.
B) Use a protic solvent.
C) Use a low temperature.
D) Both use a strong, non-nucleophilic base such as LDA and use a low temperature.
Q2) Which of the following is the intermediate for halogenation of ketones under acidic conditions?
A) An enolate
B) An enol
C) A tautomer
D) An epimer
Q3) Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?
A) The ketone undergoes a Bayer-Villigar oxidation.
B) The ketone is reduced.
C) The ketone undergoes an Aldol reaction.
D) The bromine helps to stabilize the second enolate, making the product more acidic than the starting material.
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Chapter 24: Carbonyl Condensation Reactions
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Q1) What is the name given to an Aldol reaction between two different carbonyl compounds?
A) multiple Aldol reaction
B) crossed Aldol reaction
C) differential Aldol reaction
D) versatile Aldol reaction
Q2) What is the general name for the reaction product formed in a Claisen reaction?
A) "\(\beta\)-hydroxy ester"
B) "\(\beta\)-keto ester"
C) "\(\alpha\)-keto ester"
D) "\(\gamma\)-hydroxy ester"
Q3) When is a crossed Aldol reaction said to be synthetically useful?
A) When both carbonyl compounds have \(\alpha\) hydrogens.
B) When both carbonyl compounds have no \(\alpha\) hydrogens.
C) When one carbonyl compound has no \(\alpha\) hydrogens.
D) When one carbonyl compound has no \(\beta\) hydrogens.
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Chapter 25: Amines
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Q1) Arrange the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first. \[\mathrm { CH } _ { 3 } \mathrm { CH } _
{ 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OCH } _ { 2 } \mathrm { CH } _
{ 3 } \quad \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 }
\mathrm { CH } _ { 2 } \mathrm { OH }\]
\[\mathrm { I }\quad\quad\quad\quad\quad\quad\mathrm { II
}\quad\quad\quad\quad\quad\quad\mathrm { III }\]
A) I > II > III
B) I > III > II
C) III > I > II
D) III > II > I
Q2) In the preparation of primary amines, how can direct nucleophilic substitution between NH<sub>3</sub> and alkyl halide be made more practical than reacting NH<sub>3</sub> and the alkyl halide in a 1:1 ratio?
A) Use a large excess of NH<sub>3</sub>.
B) Use a large excess of alkyl halide.
C) Use a limited amount of NH<sub>3</sub>.
D) Make the alkyl halide sterically hindered.
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Page 27

Chapter 26: Carbon-Carbon Bond Forming Reactions in Organic Synthesis
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Q1) Which of the following descriptions does not apply to methylene?
A) Methylene is sp<sup>2</sup> hybridized.
B) Methylene is a neutral, reactive intermediate.
C) Methylene is a radical intermediate.
D) The formula of methylene is :CH<sub>2</sub>.
Q2) Which of the following is not a step in the Suzuki reaction?
A) Oxidative addition of R-X to the palladium catalyst
B) Substitution of the R group to the palladium catalyst
C) Transfer of the alkyl group from the organoborane to palladium
D) Reductive elimination of R-R, forming the new C-C bond
Q3) What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have in common when they react with an alkyl halide?
A) All reactions form new carbon-carbon bonds.
B) They all use palladium as a catalyst in one step of the reaction.
C) They are all stereospecific reactions.
D) They all require harsh conditions.
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Chapter 27: Pericyclic Reactions
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Q1) Which of the following statements about a \(\pi\)* antibonding molecular orbital is true?
A) A \(\pi\)* antibonding molecular orbital is formed when two p orbitals of similar phase overlap.
B) A \(\pi\)* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap.
C) A \(\pi\)* antibonding molecular orbital is a higher-energy molecular orbital than a \(\pi\) bonding molecular orbital.
D) Both the statements "a \(\pi\)* antibonding molecular orbital is formed when two p orbitals of opposite phase overlap" and "a \(\pi\)* antibonding molecular orbital is a higher-energy molecular orbital than a \(\pi\) bonding molecular orbital" are true.
Q2) Which of the following statements about electrocyclic reactions is true?
A) An electrocyclic reaction is generally irreversible.
B) Generally, an acyclic triene is favored over a six-membered ring at equilibrium.
C) Generally, a four-membered ring is favored over an acyclic diene at equilibrium.
D) An electrocyclic reaction is generally reversible.
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Chapter 28: Carbohydrates
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Q1) Which of the following reagents will selectively oxidize an aldose to an aldonic acid?
A) PCC
B) Ag<sub>2</sub>O in NH<sub>4</sub>OH
C) FeCl<sub>3</sub>
D) HNO<sub>3</sub>
Q2) Cellulose is a polysaccharide with ________________________ linkages.
A) "\(\beta\)-1,4'-glycosidic"
B) "\(\alpha\)-1,4'-glycosidic"
C) "\(\beta\)-1,6'-glycosidic"
D) "\(\alpha\)-1,6'-glycosidic"
Q3) The branching units in amylopectin, a polysaccharide, which enable this molecule to be water soluble are connected with __________________________ linkages.
A) "\(\beta\)-1,4'-glycosidic"
B) "\(\alpha\)-1,4'-glycosidic"
C) "\(\alpha\)-1,6'-glycosidic"
D) "\(\beta\)-1,6'-glycosidic"
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Chapter 29: Amino Acids and Proteins
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Q1) Give the order (1<sup>st</sup> to last) in which the following amino acids would be eluted with a buffer of pH = 4 from a column containing a cationic-exchange resin (Dowex 50): Arg (pI = 10.8), Ser (pI = 5.7), Asp (pI = 2.8) and His (pI = 7.6).
A) His, Ser, Asp, Arg
B) Arg, His, Ser, Asp
C) His, Ser, Arg, Asp
D) Asp, Ser, His, Arg
Q2) Why does the formation of salts of a racemic mixture of N-acetyl valine with a single enantiomer of \(\alpha\)-methylbenzylamine enable the separation of the two enantiomers of N-acetyl valine?
A) They form amides.
B) They form diastereomers.
C) They form salts.
D) They form meso compounds.
Q3) Why can glycine not be resolved into two enantiomers?
A) It has no stereogenic centers.
B) It has no nitrogen atoms.
C) It has no aromatic rings.
D) It cannot be converted into a salt.
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Page 31

Chapter 30: Lipids
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Q1) Which of the following are simple lipids?
A) steroids
B) terpenes
C) waxes
D) prostaglandins
Q2) Which of the following correctly describes waxes?
A) long chain alcohols
B) long chain esters
C) long chain ethers
D) long chain fatty acids
Q3) What is (are) the basic subunits of terpenes?
A) cyclohexane
B) triacyl glycerols
C) isoprene
D) carbonyls
Q4) Which of the following fatty acids is not present in natural fats and oils?
A) hexadecanoic acid
B) heptadecanoic acid
C) octadecanoic acid
D) none of the choices
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Chapter 31: Synthetic Polymers
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Q1) What is the name given to polymers with two or more different monomers?
A) homopolymers
B) copolymers
C) block polymers
D) random polymers
Q2) Which of the following initiators can be used for anionic chain-growth polymerization?
A) benzoyl peroxide
B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Li
C) BF<sub>3</sub>
D) Al(CH<sub>2</sub>CH<sub>3</sub>)<sub>3</sub>, TiCl<sub>4</sub>
Q3) What is the name given to polymers with single monomers?
A) homopolymers
B) copolymers
C) block polymers
D) random polymers
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