

Organic Chemistry for Majors
Exam Materials
Course Introduction
Organic Chemistry for Majors delves into the structure, properties, synthesis, and reactions of organic compounds with a focus on the molecular logic that underpins organic transformations. Students explore key concepts such as bonding, stereochemistry, reaction mechanisms, and functional groups, laying the groundwork for a comprehensive understanding of organic molecular behavior. The course emphasizes critical thinking and problem-solving through practical examples and laboratory exercises, preparing students for advanced studies in chemistry, biochemistry, and related scientific fields.
Recommended Textbook
Organic Chemistry 3rd Edition by David R. Klein
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27 Chapters
3751 Verified Questions
3751 Flashcards
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Page 2

Chapter 1: A Review of General Chemistry: Electrons, Bonds, and
Molecular Properties
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Sample Questions
Q1) How many molecular orbitals are formed, when the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule?
A) 1
B) 2
C) 3
D) 4
E) 5
Answer: B
Q2) BF<sub>3</sub> has a no dipole moment. Draw the Lewis structure for BF<sub>3</sub>, showing all nonbonding electrons. Indicate the polarity of every atom in the structure using + and - notation. Explain why the molecule has no net dipole. Answer: 11ea894b_ac4f_ba1e_bba7_4bf101d49eeb_TB4454_00_TB4454_00 The trigonal planar geometry of BF<sub>3</sub> results in the cancellation of individual bond dipoles, producing a net molecular dipole of zero.
Q3) For NaSCH<sub>3</sub>, identify each bond as polar covalent, nonpolar covalent or ionic.
Answer: 11ea894b_ac41_fe39_bba7_cbd93c4dbacc_TB4454_00_TB4454_00
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Page 3

Chapter 2: Molecular Representations
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Sample Questions
Q1) Draw all the constitutional isomers with a molecular formula of C<sub>3</sub>H<sub>6</sub>O and label the functional groups in each isomer.
Answer: 11ea894b_ac5d_9d38_bba7_d92c94e321f0_TB4454_00_TB4454_00 11ea894b_ac5d_c449_bba7_671896bd267a_TB4454_00_TB4454_00
Q2) Resonance structures have _______ connectivity of atoms and _______ distribution of electrons.
A) different, same
B) same, same
C) different, different
D) same, different
E) None of these
Answer: D
Q3) Draw a bond-line structure for each constitutional isomer with a molecular formula of C<sub>2</sub>H<sub>4</sub>O.
Answer: 11ea894b_ac5a_1aa7_bba7_01dafb0d203a_TB4454_00_TB4454_00
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
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Chapter 3: Acids and Bases
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Sample Questions
Q1) 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
Q2) Which of the following compounds is more acidic? Explain why.
HF and HBr
Answer: HBr is more acidic than HF. The Br<sup>-</sup> ion has larger ionic size than the F<sup>-</sup> ion, which allows for spreading of charge over a larger volume of space. This results in a more stable anion and a weak conjugate base. HF also participates in hydrogen bonding and is a weak acid.
Q3) What is a cation?
A) a negatively charged ion
B) a positively charged ion
C) a sodium atom
D) a hydrogen molecule
Answer: B
Q4) Draw the conjugate acid of CH<sub>3</sub>OCH<sub>3</sub>
Answer: 11ea894b_ac6a_bc2d_bba7_b95ff4ea07c8_TB4454_00_TB4454_00
Page 5
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Chapter 4: Alkanes and Cycloalkanes
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Sample Questions
Q1) What is the structure of 3-ethyl-2,4,6-trimethyloctane?
Q2) Draw a chair conformation of methylcyclohexane.
Q3) 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?
Q4) Of the following isomers of C<sub>9</sub>H<sub>20</sub>, which is the most stable?
A) nonane
B) 3-methyloctane
C) 2,2-dimethylheptane
D) 2,2,3,4-tetramethylpentane
Q5) The process that converts straight-chain alkanes into branched hydrocarbons is called _____________.
A) hydrogenation
B) cracking
C) reforming
D) hydrolysis
Q6) What is the structure of an isopropyl group?
Q7) Draw the lowest energy chair conformer of the most stable isomer of 4-isopropyl-1,2-dimethylcyclohexane.
Page 6
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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>3</sub> II. -CN III. -CH<sub>2</sub>OH IV. -Br
Q2) 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?
Q3) What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of 52?
A) 61
B) 64
C) 0
D) 61
Q4) 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>
Q5) Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.
I. -F II. -H III. -OH IV. -SH
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Chapter 6: Chemical Reactivity and Mechanisms
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Sample Questions
Q1) 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.
Q2) Draw an energy diagram for an endothermic reaction with two steps.
Q3) 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?
Q4) Which of the following describes the effect of a catalyst on a reaction?
A) It lowers the free energy of the products.
B) It makes the reactants less stable.
C) It changes the equilibrium constant.
D) It lowers the energy of activation.
Q5) 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
Q6) Does a reaction with a positive S and a negative H favor reactants or products?
Page 8
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Chapter 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions
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Sample Questions
Q1) Provide the structure for 1-chloro-4-isopropylheptane.
Q2) Which of the following is NOT a nucleophile?
A) OH<sup>-</sup>
B) NH<sub>3</sub>
C) CH<sub>3</sub>OH
D) NH<sub>4</sub><sup>+</sup>
E) All of these
Q3) Draw the E isomer of 2-methyl-3-heptene.
Q4) Draw the structure of 2,3-dimethyl-1-pentene.
Q5) Which of the following is true about the stereochemistry of S<sub>N</sub>1 reaction?
A) retention of configuration at the electrophilic center
B) inversion of configuration at the electrophilic center
C) 50:50 mixture of retention and inversion of configuration at the electrophilic center
D) slightly more inversion than retention at the electrophilic center
E) slightly more retention than inversion at the electrophilic center
Q6) Draw the Z isomer of 3,4-dimethyl-3-hexene.
Q7) Which pattern of arrow pushing is associated with the first step in any dehydration reaction?
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Chapter 8: Addition Reactions of Alkenes
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Sample Questions
Q1) Treating 2-methyl-2-pentene with Br<sub>2</sub> is expected to produce which of the following as the major product?
A) 2,3-dibromo-2-methylpentane
B) 2,2-dibromo-3-methylpentane
C) 3,3-dibromo-2-methylpentane
D) 2-bromo-2-methylpentane
E) 3-bromo-2-methylpentane
Q2) Which of the following will yield 2-methylpentane upon catalytic hydrogenation?
A) 2-methyl-1-pentene
B) 2-methyl-2-pentene
C) 4-methyl-2-pentene
D) 4-methyl-1-pentene
E) All of the above
Q3) For an addition reaction, why does free energy, \(\Delta\)G, become more positive with increasing temperature?
A) The positive entropy dominates at high temperature.
B) The negative entropy dominates at high temperature.
C) The positive enthalpy dominates at high temperature.
D) The negative enthalpy dominates at high temperature.
E) The enthalpy and entropy cancel at high temperature.
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Chapter 9: Alkynes
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Sample Questions
Q1) Provide the IUPAC name for (CH<sub>3</sub>)<sub>2</sub>CHC CCH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub >.
A) 1,1,5,5,5-pentamethyl-2-pentyne
B) 1,1,1,5,5-pentamethyl-3-pentyne
C) 2,2,6-trimethyl-4-heptyne
D) 2,6,6-trimethyl-3-heptyne
E) tert-butylisopropylacetylene
Q2) Consider the list of alkyne addition reactions below, and select all those that involve an enol intermediate.
A) Hydroboration/oxidation
B) HgSO<sub>4</sub> catalyzed hydration in dilute H<sub>2</sub>SO<sub>4</sub>
C) Hydrohalogenation
D) Both A and B
E) Both A and C
Q3) Give the hybridization for the carbanion in the acetylide ion.
A) sp
B) sp<sup>2</sup>
C) sp<sup>3</sup>
D) s<sup>2</sup>p
E) s<sup>2</sup>p<sup>2</sup>
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Chapter 10: Radical Reactions
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Sample Questions
Q1) Identify an example of initiation.
A) homolytic cleavage
B) heterolytic cleavage
C) hydrogen abstraction
D) coupling
E) hydrogen addition
Q2) Give the arrows to show the propagation steps for the autooxidation of diethyl ether.
Q3) Identify an example of termination.
A) homolytic cleavage
B) heterolytic cleavage
C) hydrogen abstraction
D) coupling
E) hydrogen addition
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) Identify the best solvent for Green Chemistry.
A) methylene chloride
B) water
C) ethanol
D) methanol
E) ethyl acetate
Q2) Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methylcyclohexanol to a secondary position?
A) 1. KOtBu; 2. Hg(OAc)<sub>2</sub>, H<sub>2</sub>O; 3. NaBH<sub>4</sub>
B) 1. TsCl, pyr; 2. KOtBu; 3. BH<sub>3</sub>-THF; 4. H<sub>2</sub>O<sub>2</sub>, NaOH
C) 1. H<sub>2</sub>SO<sub>4</sub>, heat; 2. BH<sub>3</sub>THF; 3. H<sub>2</sub>O<sub>2</sub>, NaOH
D) 1. TsCl, pyr; 2. NaOH; 3. BH<sub>3</sub>THF; 4. H<sub>2</sub>O<sub>2</sub>, NaOH E) C and D will both work
Q3) Propose a synthesis of propanoic acid from acetylene.
Q4) Devise a synthetic route to prepare 1,7-heptanediol from propene.
Q5) Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.
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Page 13

Chapter 12: Alcohols and Phenols
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Sample Questions
Q1) Provide the reagents necessary to convert 3-methyl-2-butanol to 2-bromo-3-methylbutane.
A) conc. HBr
B) Br<sub>2</sub>
C) NaBr, H<sub>2</sub>SO<sub>4</sub>
D) PBr<sub>3</sub>
E) HBr, peroxide
Q2) Identify the alcohol in alcoholic drinks.
A) methanol
B) 2-propanol
C) ethanol
D) 1-butanol
E) 1-propanol
Q3) Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.
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) Provide the structure for 6-sec-butyl-7,7-dimethyl-4-decanol.
Q6) Give the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol.
Page 14
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Chapter 13: Ethers and Epoxides; Thiols and Sulfides
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Sample Questions
Q1) Provide the structure for oxane.
Q2) Draw all constitutional isomers with molecular formula C<sub>6</sub>H<sub>14</sub>O having an ether functional group and provide the IUPAC name for each isomer.
Q3) What is the common name for CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>CH <sub>3</sub>?
A) dibutyl ether
B) 1-propoxypropane
C) 1-propoxyhexane
D) dipropyl ether
E) none of these
Q4) 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>3</sub>
Q5) Provide the structure for (2S,5R)-5-ethoxy-2-octanol.
Q6) Provide the structure for (R)-1,1-dimethoxy-3-phenoxycyclopentane.
Page 15
Q7) What is the correct structure for phenylthiol?
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Chapter 14: Infrared Spectroscopy and Mass Spectrometry
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Sample Questions
Q1) Which of the following information is primarily obtained from infrared spectroscopy?
A) arrangement of carbon and hydrogen atoms in a compound
B) molecular weight of a compound
C) any conjugated system present in a compound
D) functional groups present in a compound
E) all of these
Q2) A stationary phase separates the components of a mixture based on their _____________ and __________ .
A) boiling points, their affinity for the stationary phase
B) melting points, their repulsion for the stationary phase
C) molecular weights, melting points
D) solubility in water, in methanol
E) heat of vaporization, heat of sublimation
Q3) Electrospray ionization is used to obtain mass spectra of proteins because:
A) it allows for faster fragmentation of the molecular ion
B) the molecular ion usually does not undergo fragmentation
C) it allows for slow fragmentation of the molecular ion
D) the proteins are liquids
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 type(s) of protons are chemically equivalent?
A) homotopic
B) enantiotopic
C) diastereotopic
D) A & B
E) B & C
Q2) Identify the splitting pattern for a CH in an off-resonance decoupled <sup>13</sup>C NMR spectrum.
A) no peak
B) singlet
C) doublet
D) triplet
E) quartet
Q3) The strength of the magnetic field is a determining factor for the range of _______that must be used for NMR spectrometer.
A) temperature
B) frequencies
C) tesla
D) none of these
E) spin states
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Chapter 16: Conjugated Pi Systems and Pericyclic Reactions
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Sample Questions
Q1) Identify the MOs that react to form cyclohexene via a Diels-Alder Reaction.
A) LUMO of 1,3-butadiene and HOMO of ethylene
B) LUMO of 1,3-butadiene and LUMO of ethylene
C) HOMO of 1,3-butadiene and HOMO of ethylene
D) HOMO of 1,3-butadiene and LUMO of ethylene
Q2) What is the Cope rearrangement?
A) [2,2] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms
B) [2,2] sigmatropic rearrangement with heteroatoms
C) [2,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms
D) [2,3] sigmatropic rearrangement with heteroatoms
E) [3,3] sigmatropic rearrangement with all atoms of the cyclic transition step are carbon atoms
Q3) Provide the structure of the 1,4 addition product for the reaction of 1,3-hexadiene with Br<sub>2</sub>/CCl<sub>4</sub>.
Q4) Identify the light-sensitive compound in rods.
Q5) Provide the structure for (Z)-2-methyl-2,4-hexadiene.
Q6) Provide the structure for (S,E)-3-t-butyl-4-methyl-1,4-hexadiene.
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Chapter 17: Aromatic Compounds
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Sample Questions
Q1) According to the molecular orbital theory how many molecular orbitals are formed when the six p-orbitals of benzene combine?
A) 6
B) 5
C) 4
D) 3
E) 2
Q2) Which of the following describes the current view of the two Kekulé structures for benzene?
A) they are both correct structures for benzene
B) the two structures are in equilibrium
C) the two structures adequately describe benzene
D) benzene is a resonance hybrid of the two structures
E) None of the above
Q3) The carbon-carbon bonds in benzene are _________.
A) of equal length and are shorter than the double bond
B) of equal length and are midway between a single bond and a double bond
C) of equal length and are longer than the single bond
D) of unequal length and alternate as single and double bonds
E) none of these
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Chapter 18: Aromatic Substitution Reactions
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Sample Questions
Q1) Which one of the following substituents will not direct the incoming group to the meta position during electrophilic aromatic substitution?
A) -NO<sub>2</sub>
B) -C\(\equiv\)N
C) -OCH<sub>3</sub>
D) -COOH
E) all of these
Q2) Give the preferred products from the nitration of bromobenzene.
Q3) An alkyl group ___________ the benzene ring to make it __________ reactive than benzene.
Q4) Identify the electrophile in the nitration of benzene.
A) sulfonium ion
B) nitrogen dioxide
C) nitronium ion
D) nitrous oxide
E) Nitrogen dioxide
Q5) A halogen ___________ the benzene ring; the ring is __________ reactive than benzene.
Q6) List the three steps involved in an electrophilic aromatic substitution reaction.
Page 20
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Chapter 19: Aldehydes and Ketones
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Sample Questions
Q1) Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.
Q2) Provide the structure for (S)-3-chlorocyclohexanone.
Q3) Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.
Q4) Name the aldehyde or ketone that is found in nail polish remover.
A) ethanol
B) 2-butanone
C) acetone
D) formaldehyde
E) diethyl ether
Q5) Suggest a stepwise synthesis for pentanal from butanal.
Q6) The <sup>1</sup>H NMR spectrum of a compound with formula C<sub>7</sub>H<sub>14</sub>O shows only two signals. Which one of the following is a possible structure for this compound?
A) 2-heptanone
B) 3-heptanone
C) 2,4-dimethyl-3-pentanone
D) 2,2-dimethyl-3-pentanone
E) Two of the above
Q7) Provide the structure for benzophenone.
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Chapter 20: Carboxylic Acids and Their Derivatives
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Sample Questions
Q1) Provide the structure for benzyl propionate.
Q2) A compound with molecular formula C<sub>9</sub>H<sub>10</sub>O<sub>2</sub> exhibits a triplet at \(\delta\) 1.2 (3H), a quartet at \(\delta\) 2.6 (2H), a doublet at \(\delta\) 7.3 (2H), a doublet at \(\delta\) 8.0 (2H) and a singlet at \(\delta\) 11 (1H) in its <sup>1</sup>H NMR spectrum. What is the structure for this compound?
Q3) Give the IUPAC name for malonic acid.
A) ethanedioic acid
B) propanedioic acid
C) butanedioic acid
D) pentanedioic acid
E) benzoic acid
Q4) Provide the structure for cyclopentanecarbonyl chloride.
Q5) 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?
Q6) Provide the structure for 5-chloro-3-isopropyloctanoic acid.
Q7) 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) Give the organic by-product in a haloform reaction.
Q2) Provide the reagents necessary to convert acetophenone to benzoic acid.
A) PCC/CH<sub>2</sub>Cl<sub>2</sub>
B) 1. NaOH/Br<sub>2</sub>
2) H<sub>3</sub>O<sup>+</sup>
C) 1. KMnO<sub>4</sub>/NaOH/H<sub>2</sub>O
2) H<sub>3</sub>O<sup>+</sup>
D) 1. Br<sub>2</sub>/PBr<sub>3</sub>
2) H<sub>2</sub>O
E) both B and C
Q3) 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
Q4) Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.
Q5) An intermolecular Claisen condensation is called a _____________.
Page 23
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Chapter 22: Amines
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Sample Questions
Q1) Which of the following is a tertiary amine?
A) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> B)
CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> C)
(CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>NCH<sub>2</sub>CH(CH<sub>3</sub> )<sub>2</sub>
D) (CH<sub>3</sub>CH<sub>2</sub>)<sub>4</sub>N<sup>+ </sup>OH<sup>-</sup>
E) (CH<sub>3</sub>CH<sub>2</sub>)<sub>3</sub>CNH<sub>2</sub>
Q2) Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.
Q3) Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.
Q4) Predict the major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C followed by o-ethylphenol? 2
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) 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
Q2) Which of the following is not a step in the Heck reaction catalytic cycle?
A) transmetallation
B) reductive elimination
C) syn-elimination
D) oxidative addition
E) syn-addition
Q3) 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
Q4) Why is ethanol not a viable solvent in the synthesis of Grignard reagents?
Q5) Explain why the solvent for a Grignard reaction must be free of water.
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Chapter 24: Carbohydrates
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Sample Questions
Q1) Which of the following best describes the relationship between D-glucose and D-fructose?
A) enantiomers
B) epimers
C) anomers
D) constitutional isomers
E) diastereomers
Q2) Provide the structure for uridine.
Q3) Identify the classification for D-galactose.
A) aldotetrose
B) ketotetrose
C) aldopentose
D) ketopentose
E) aldohexose
Q4) Of the possible stereoisomers for fructose, how many are D-isomers?
A) 8
B) 6
C) 10
D) 2
E) 4
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Chapter 25: Amino Acids, Peptides, and Proteins
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Sample Questions
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) Which of the following aldehydes would produce glycine using a Strecker synthesis?
A) methanal
B) ethanal
C) propanal
D) butanal
Q3) List the reason why the s-trans conformation of a peptide bond is more stable than the s-cis conformation.
A) there is a restricted rotation around the peptide bond
B) rotation is allowed around the peptide bond
C) it has reduced steric hindrance
D) none of these
Q4) How will you prepare glycine staring with ethanol and using a Hell-Volhard-Zelinski reaction?
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Chapter 26: Lipids
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Sample Questions
Q1) Why is decanol more efficient at crossing the cell membrane than hexanol?
Q2) Which one of the following is a female sex hormone?
A) estrone
B) androsterone
C) cortisone
D) lanosterol
E) nandrolone
Q3) Phosphoglycerides differ from triglycerides in that one of the three fatty acid residues is replaced by a(n) ______ group.
A) thioester
B) phosphoester
C) thiol
D) alcohol
E) ester
Q4) Which one of the following is not classified as an eicosanoid?
A) leukotrienes
B) prostaglandins
C) thromboxanes
D) prostacyclins
E) cortisone

Page 28
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Chapter 27: Synthetic Polymers
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Sample Questions
Q1) Provide the structure of a region of a block copolymer constructed from isobutylene and vinyl fluoride.
Q2) A syndiotactic polymer has a _______ configuration.
A) random
B) alternating
C) same
D) block
E) graft
Q3) Which of the following is used as an initiator in anionic 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) H<sub>2</sub>SO<sub>4</sub>
E) none of these
Q4) Identify the polymer that is used in bicycle helmets.
A) Nylon 6
B) Teflon
C) Kevlar
D) Lexan
E) Nylon 6,6

Page 29
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