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44. As applied to the chemistry of amino acids, what is the definition for the isoelectric
point?
A) The pH at which the amino acid exists primarily in its acidic form.
B) The pH at which the amino acid exists primarily in its basic form.
C) The pH at which the amino acid exists as a mixture of isomers.
D) The pH at which the amino acid exists primarily in its neutral form.

Chapter 20: Introduction to Carbonyl Chemistry;

Organometallic Reagents; Oxidation and Reduction

1. What is the name of the general reaction type that aldehydes and ketones undergo?
A) Electrophilic addition C) Nucleophilic substitution
B) Nucleophilic addition D) Electrophilic substitution

2. What is the name of the general reaction type that carboxylic acids, esters, and amides
undergo?
A) Electrophilic acyl addition C) Nucleophilic acyl substitution
B) Nucleophilic acyl addition D) Electrophilic acyl substitution

3. What are the two steps in a nucleophilic addition mechanism?

A) Nucleophilic attack followed by protonation.
B) Nucleophilic attack followed by deprotonation.
C) Nucleophilic attack followed by substitution.
D) Nucleophilic attack followed by elimination.

4. Which of the following terms explain why aldehydes are more reactive than ketones?
A) Electronegativity and resonance C) Electronegativity and hybridization
B) Hybridization and resonance D) Sterics and electronics

5. Why are ketones less reactive than aldehydes?

A) Ketones are more sterically hindered.

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B) Ketones are less electron deficient due to donation from the two alkyl groups.
C) The statement is false; Ketones are more reactive than aldehydes.
D) Both (a) Ketones are more sterically hindered and (b) Ketones are less electron
deficient due to donation from the two alkyl groups.

6. If a compound is reduced, what is the result?

A) Fewer C-H bonds
B) Increased number of C-H bonds
C) Fewer C-Z bonds
D) Both increased number of C-H bonds and fewer C-Z bonds

7. Rank the following compounds in order of decreasing reactivity in nucleophilic addition

reactions, starting with the most reactive compound.

A) III > I > IV > II C) IV > II > III > I

B) II > IV > I > III D) II > IV > III > I

8. Rank the following compounds in order of increasing reactivity in nucleophilic acyl

substitution reactions, starting with the least reactive compound.

A) III < II < I B) II < III < I C) III < I < II D) II < I < III

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9. What is the product of the following reaction?

A) I B) II C) III D) IV

10. What is the product of the following reaction?

A) I B) II C) III D) IV

11. What is the starting material in the following reaction?

A) I B) II C) III D) IV

12. Which reagent can be used to reduce the alkene in cyclopentenone?

A) NaBH4 B) LiAlH4 C) H2 and Pd-C D) DIBAL-H

13. Which reagent can be used to reduce the carbonyl in methyl vinyl ketone?
A) NaBH4/CH3OH B) H2 and Pd-C C) FeCl3 D) NaH

14. Which reagent can be used to reduce an acid chloride to an aldehyde?

A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3

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15. What reagent would be used to reduce an amide to an amine?

A) NaBH4 B) LiAlH(OtBu)3 C) LiAlH4 D) FeCl3

16. What is the product of the following reaction?

A) I B) II C) III D) IV

17. What is the product of the following reaction?

A) I B) II C) III D) IV

18. What will be the product of the following reaction (before any aqueous work-up)?

A) I B) II C) III D) IV

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19. Why would the alcohol in the following compound need to be protected before
reaction?

A) If it isn't protected, the product will be a carboxylic acid.

B) The Grignard reagent will react with the alcohol before the ketone.
C) Magnesium is Lewis acidic and will coordinate with the alcohol.
D) There is no need to protect the alcohol.

20. What is the purpose of a silyl ether?

A) To protect esters from organometallic reagents and other reagents
B) To protect ketones from organometallic reagents and other reagents
C) To protect alcohols from organometallic reagents and other reagents
D) To prevent the formation of carboxylic acids

21. What reagent can be used to cleave a silyl ether protecting group?
A) NaOMe B) MeMgBr C) Bu4NF D) Pd/C

22. What is the product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II

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23. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

24. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

25. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

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26. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

27. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

28. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

29. Rank the carbon-metal bond in the following organometallic reagents in order of
decreasing polarity, starting with the most polar.

A) II > I > III B) II > III > I C) III > I > II D) III > II > I

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30. Which of the following statements about organometallic reagents is not true?
A) Organometallic reagents contain a carbon atom bonded to a metal.
B) The more polar the carbon-metal bond, the more reactive the organometallic
reagent.
C) Organometallic reagents react as bases and nucleophiles.
D) Organometallic reagents are strong acids that readily donate a proton to water.

31. What is the product of the following reaction?

A) I B) II C) III D) IV

32. What is the product of the following reaction?

A) I B) II C) III D) IV

33. What is the major organic product of the following reaction?

A) Only I B) Only II C) Only III D) Only I and II

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34. What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?

A) Only I B) Only II C) Only III D) Only I and II

35. What is the major organic product in the following sequence of reactions?

A) I B) II C) III D) IV

36. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

37. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

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38. What is the major organic product in the following sequence of reactions?

A) I B) II C) III D) IV

39. What is the missing reagent in the reaction below?

A) [1] Mg, [2] CO2, [3] acidic work-up C) [1] CO2, [2] acidic work-up
B) [1] CO2, [2] NaOH D) LiAlH4

40. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

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41. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

42. What is the major organic product of the following reaction?

A) I B) II C) III D) IV

43. What is the missing reagent in the reaction below?

A) Et2CuLi then H2O

B) EtMgBr then H2O
C) NaBH4/CH3OH
D) H2, Pd-C

44. What is the missing reagent in the reaction below?

A) PhMgBr then H2O C) Ph2CuLi then H2O

B) Benzene, AlCl3 D) PhLi then H2O

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45. What is the missing reagent in the reaction below?

A) NaBH4/CH3OH
B) H2, Pd-C
C) LiAlH4 then H2O
D) MeMgBr then H2O

46. What is the starting material in the reaction below?

A) Bromobenzene
B) Benzyl bromide
C) Benzoic acid
D) Lithium benzoate

47. What is the missing reagent in the reaction below?

A) NaBH4/CH3OH B) DIBAL-H C) H2, Pd-C D) LiAlH4 then H2O

48. Rank the following compounds in order of increasing reactivity toward the nucleophilic
hydride reagent, NaBH4.

A) I < II < III B) III < II < I C) II < III < I D) II < I < III

49. A carbonyl group, C=O, and an alkene, C=C, double bonds, are both sp2 hybridized.
However, the chemistry of these two functional groups is very different. This can be
explained by which of the following statements?
A) The bond angle of the carbonyl is larger than the bond angle of the alkene.
B) The electronegative oxygen of the C=O group makes this bond polar.
C) The bond of the C=C is longer that the bond of the C=O.

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D) There is more steric crowding in the carbonyl than in the alkene.

50. Both LiAlH4 and NaBH4 are reducing agents. Which statement about these reagents is
true?
A) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
greater than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing
agent.
B) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
greater than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent.
C) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
less than the polarity of the Al-H bond, so LiAlH4 is the stronger reducing agent.
D) Both reagents contain polar metal-hydrogen bonds. The polarity of the B-H bond is
less than the polarity of the Al-H bond, so LiAlH4 is the weaker reducing agent.

51. If the starting material has no stereogenic centers, when carbonyl compounds are
reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is
formed, what will the composition of the product mixture be?
A) Forms a racemic mixture of the two possible enantiomers
B) Forms more of one enantiomer than another because of steric reasons around the
carbonyl
C) Forms more of one enantiomer than another depending on the temperature of the
reaction
D) Forms different products depending on the solvent used

52. Rank the following compounds in order of increasing reactivity (least to most reactive)
with respect to acyl substitution.

I. methyl benzoate
II. benzoylchloride
III. benzamide
A) III< I < II B) II < I < III C) II < III < I D) I < III < II

53. The behavior of acid chlorides is different from that of aldehydes in a reaction with a
nucleophile because
A) The acid chloride contains a better leaving group.
B) The aldehyde is more easily oxidized.
C) The carbonyl of the aldehyde is more positive.
D) The carbonyl of the aldehyde is less hindered.

Chapter 21: Aldehydes and Ketones – Nucleophilic Addition

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1. Which is the most reactive carbonyl compound?

A) I B) II C) III D) IV

2. What is the IUPAC name for the following compound?

A) pivaldehyde C) tert-butyl aldehyde

B) 2,2-dimethylpropanal D) 2,2-dimethylpentanal

3. What is the structure of 3-methylcyclohexanone?

A) I B) II C) III D) IV

4. What is the structure of 2-trifluoromethyl-2-methoxybutanal?

A) I B) II C) III D) IV

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5. What is the structure of benzophenone?

A) I B) II C) III D) IV

6. 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-1.
B) An aldehyde has a carbonyl stretch at 1820 cm-1.
C) An aldehyde has two C-H stretches between 2700-2850 cm-1.
D) A ketone has no C-H stretches.

7. Which of the following will have the highest wave number for the carbonyl stretch in
the IR spectrum?

A) I B) II C) III D) IV

8. Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a
ketone?
A) An aldehyde has a C-H stretch (one or two) between 2700-2830 cm-1.
B) An aldehyde has a proton signal between 9-10 ppm.
C) A ketone has signals around 2-3 ppm.
D) A ketone has a signal around 200 ppm.

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9. What compound is consistent with the following 1H NMR spectrum?

A) Acetone B) Propanal C) Cyclobutanone D) 2-butanone

10. Which of the following oxidants would work for the following reaction?

A) H2Cr2O7 B) FeCl3 C) I2 D) Ag2O

11. What is the first step in nucleophilic addition under acidic conditions?
A) Protonation of the nucleophile C) Loss of water
B) Addition of the nucleophile D) Protonation of the carbonyl

12. Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition
of a Grignard reagent to a ketone?
A) Because the Grignard reagent will react with the acid and be quenched.
B) Because the ketone will be protonated and thus unreactive.
C) Because the ketone will form an unreactive enol.
D) Because the Grignard reagent won't dissolve in aqueous solutions.

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13. What is the major organic product obtained from the following sequence of reactions?

A) I B) II C) III D) IV

14. Is the following reaction reversible and, if so, under what conditions?

A) No C) Yes, using Pd/C

B) Yes, under acidic conditions D) Yes, under basic conditions

15. What would you use to prepare the following ylide from the starting phosphonium salt?

A) butyl lithium C) triphenylphosphine

B) 1-bromo-2-methylpropane D) acetic acid

16. What is the driving force for the Wittig reaction?

A) The formation of an alkene
B) The deprotonation of a phosphonium salt
C) The elimination of triphenylphosphine oxide
D) The formation of a phosphonium salt

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17. What is the product of the following reaction?

A) I B) II C) III D) IV

18. 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.

19. What is the product of the following reaction?

A) I B) II C) III D) IV

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20. What is the product of the following reaction?

A) I B) II C) III D) IV

21. What needs to be done to make the following reaction proceed?

A) Heat the reaction.

B) Add an acid catalyst only.
C) Add a base catalyst only.
D) Heat the reaction and add an acid catalyst.

22. What needs to be done to make the following reaction go to starting materials?

A) Heat the reaction. C) Add aqueous base.

B) Add aqueous acid. D) Add water.

23. What sequence of reactions is required for the following transformation?

A) [1] NaOMe, [2] acetone C) [1] Ph3P, [2] KOtBu, [3] acetone
B) [1] Ph3P, [2] acetone D) acetone, heat

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24. What is the product?

A) I B) II C) III D) IV

25. What is the product of the following reaction?

A) I B) II C) III D) IV

26. What is (are) the product(s) of the following reaction?

A) I only B) II only C) III only D) II and III

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27. What is the product of the following reaction?

A) I B) II C) III D) IV

28. What is (are) the product(s) of the following reaction?

A) I only B) II only C) III only D) II and III

29. What is the product of the following reaction?

A) I B) II C) III D) IV

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30. What is the product of the following sequence of reactions?

A) I B) II C) III D) IV

31. What is the missing reagent in the reaction below?

A) Ethyl amine, mild acid C) Diethylamine, strong acid

B) Diethylamine, mild acid D) Diethylamine, NaOMe

32. What is the missing reagent in the reaction below?

A) I B) II C) III D) IV

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33. What is the cyclic hemiacetal product formed from intramolecular cyclization of the
following hydroxy aldehyde?

A) I B) II C) III D) IV

34. What is the missing reagent in the reaction below?

A) Methanol, acid B) Ethanol, acid C) NaOEt D) NaOMe

35. Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO
with Ph3P CHCH3?

A) Only I B) Only II C) Only III D) Only I and II

36. What is the IUPAC for the following compound?

A) 1-formyl-2-nitropropane C) 2-nitrobutanal
B) 1-formyl-3-nitrobutane D) 3-nitrobutanal

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37. What is the product of the following reaction?

A) I B) II C) III D) IV

38. How would the following compounds be distinguishable using IR and 1H NMR
spectroscopy?

A) The 1H NMR spectrum of compound I will have two singlets.

B) The C=O absorption in the IR spectrum of compound I will be at a higher wave
number than that of compound II.
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of
about 4.
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O
absorption in the IR spectrum of compound I will be at a higher wave number than
that of compound II.

39. Name the following aldehyde.

A) 1-methylcyclopentanal C) 2-methylcyclopentanecarbaldehyde
B) 2-methylcyclopentanal D) 1-methylcyclopentanylcarbaldehyde

40. Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling
point of 118 °C. What accounts for this difference in boiling points?
A) Butanol is polar while butanal is not polar.

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B) Butanol can exhibit dipole-dipole interactions while butanal cannot.

C) Butanol can hydrogen bond and butanal cannot hydrogen bond.
D) Butanal is less sterically hindered than butanol.

41. Identify how you could synthesize an enamine.

A) React a ketone or an aldehyde with a secondary amine.
B) React a ketone or an aldehyde with a primary amine.
C) React a ylide with a primary amine.
D) React a ylide with a secondary amine.

42. When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the
product called?
A) Hemiacetal B) Di-ether C) Di-alkoxy alkane D) Acetal

43. Cyclic acetals are used as protecting groups for ketones or aldehydes because they are
inert to all of the following reagents except
A) aqueous acid. C) oxidizing reagents.
B) aqueous base. D) reducing reagents.

44. 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.

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45. What is the product of the following reaction?

A) I B) II C) III D) IV

Chapter 22: Carboxylic Acids and Derivatives

1. Which of the following is a lactam?

A) I B) II C) III D) IV

2. Why is an amide less reactive to nucleophilic acyl substitution than an acid chloride?
A) Nitrogen is a better leaving group.
B) Chloride is a better leaving group.
C) Nitrogen donates more electron density into the carbonyl.
D) The amide anion is less basic.

3. What is the IUPAC name for the following compound?

A) methyl 3-methylbutanamide C) N-methyl 3-methylhexanamide

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