Chapter 17 Carbonyl, Oxidation, Reduction Test Bank Answers

Organic Chemistry, 6e (Smith)

Chapter 17 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

B) Nucleophilic addition

C) Nucleophilic substitution

D) Electrophilic substitution

2) What is the name of the general reaction type that carboxylic acids, esters, and amides undergo?

A) Electrophilic acyl addition

B) Nucleophilic acyl addition

C) Nucleophilic acyl substitution

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

B) Hybridization and resonance

C) Electronegativity and hybridization

D) Sterics and electronics

5) Why are ketones less reactive than aldehydes?

A) Ketones are more sterically hindered

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 Ketones are more sterically hindered and 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

B) II > IV > I > III

C) IV > II > III > I

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

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

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

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

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

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

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

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

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

B) [1] CO2, [2] NaOH

C) [1] CO2, [2] acidic work-up

D) LiAlH4

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

A) I

B) II

C) III

D) IV

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

B) Benzene, AlCl3

C) Ph2CuLi then H2O

D) PhLi then H2O

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.

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 reactions 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

54) What is the missing reagent in the reaction below?

A) [1] LiAlH4, [2] H2O

B) [1] CH3MgBr (excess), [2] H2O

C) [1] (CH3)2CuLi (excess), [2] H2O

D) [1] DIBAL-H, [2] H2O

55) What is the missing reagent in the reaction below?

A) [1] LiAlH4, [2] H2O

B) [1] CH2=CHLi, [2] H2O

C) [1] (CH2=CH)2CuLi, [2] H2O

D) [1] DIBAL-H, [2] H2O

56) What is the major product from the following reaction?

A) I

B) II

C) III

D) IV

57) What is the major product from the following reaction?

A) I

B) II

C) III

D) IV

58) What is the major product from the following reaction?

A) I

B) II

C) III

D) IV

59) What is the major product from the following reaction?

A) I

B) II

C) III

D) IV