Deck 12: Alcohols From Carbonyl Compounds

Question 1

The following transformation would be considered a(n)?

A)Reduction
B)Oxidation
C)Addition
D)Elimination
E)Rearrangement

Answer 1

Oxidation

Question 2

The following transformation would be considered a(n)?

A)Reduction
B)Oxidation
C)Addition
D)Elimination
E)Rearrangement

Answer 2

Oxidation

Question 3

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Answer 3

III,I,II

Question 4

When nucleophilic addition to a carbonyl group occurs,the carbon attacked undergoes this hybridization change:

A)sp² $\to$ sp³
B)sp $\to$ sp²
C)sp $\to$ sp³
D)sp³ $\to$ sp²
E)sp² $\to$ sp

Question 5

The following transformation would be considered a(n)?

A)Reduction
B)Oxidation
C)Addition
D)Elimination
E)Rearrangement

Question 6

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)I,III,II
C)II,I,III
D)III,I,II
E)III,II,I

Question 7

The following transformation would be considered a(n)?

A)Reduction
B)Oxidation
C)Addition
D)Elimination
E)Rearrangement

Question 8

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Question 9

Which of these transformations cannot be classified as a reduction?

A)RCH₂Cl $\to$ RCH₃
B)RCH=CH₂ $\to$ RCH₂CH₃
C)RCOOH $\to$ RCH₂OH
D)
E)All of these are reductions.

Question 10

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Question 11

Which reaction is an oxidation?

A)RCHO $\to$ RCO₂H
B)RCH₂OH $\to$ RCHO
C)RCH₂OH $\to$ RCO₂H
D)None of these choices.
E)All of these choices.

Question 12

The following transformation would be considered a(n)?

A)Reduction
B)Oxidation
C)Addition
D)Elimination
E)Rearrangement

Question 13

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Question 14

The following transformation would be considered a(n)?

A)Reduction
B)Oxidation
C)Addition
D)Elimination
E)Rearrangement

Question 15

The following transformation would be considered a(n)?

A)reduction
B)oxidation
C)addition
D)elimination
E)rearrangement

Question 16

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)I,III,II
C)II,I,III
D)III,II,I
E)III,I,II

Question 17

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Question 18

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Question 19

List the following compounds in order of increasing level of oxidation:

A)I,II,III
B)III,II,I
C)II,I,III
D)III,I,II
E)I,III,II

Question 20

Which of the following resonance structures is not a significant contributor to the hybrid for the carbonyl group?

A)I
B)II
C)III
D)Neither II nor III is important.
E)All are significant contributors.

Question 21

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CH₂OH into CH₃CH₂CH=CHCH₂CH₂CHO?

A)KMnO₄,OH^-
B)CrO₃ / H₂SO₄
C)PCC in CH₂Cl₂
D)(i)(COCl)₂,DMSO,-60 ^oC,(ii)Et₃N
E)Two of these choices.

Question 22

Which of these compounds will not be reduced by LiAlH₄?

A)CH₃CH₂CH₂CH=CH₂
B)
C)
D)
E)

Question 23

List the following alkyl halides in order of increasing ease of Grignard formation:

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

Question 24

Select the correct reagent(s)for the following reaction:

A)LiAlH₄/ether; then H₃O⁺
B)NaBH₄; then H₃O⁺
C)H₂ with Pt/C
D)Two of these choices.
E)All of these choices.

Question 25

Select the correct reagent(s)for the following reaction:

A)LiAlH₄/ether; then H₃O⁺
B)NaBH₄; then H₃O⁺
C)H₂ with Pt/C
D)Two of these choices.
E)All of these choices.

Question 26

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CHO into CH₃CH₂CH₂CH₂CH₂CH₂CH₂OH?

A)KMnO₄
B)NaBH₄
C)Br₂ in CCl₄
D)H₂,Ni
E)Two of these choices.

Question 27

Which of the reagents listed below would efficiently accomplish the transformation of 3-methyl-3-cyclopentenone into 3-methyl-3-cyclopentenol?

A)i)LiAlH₄; ii)H₂O
B)NaBH₄,H₂O
C)H₂,Pd
D)More than one of these choices.

Question 28

In the reaction of carbonyl compounds with LiAlH₄,the effective reducing species is:

A)Li⁺
B)Al⁺³
C)AlH₄^-
D)AlH₃
E)H^-

Question 29

Which reagent(s)would you use to convert CH₃(CH₂)₆CO₂H to CH₃(CH₂)₆CH₂OH?

A)NaBH₄/H₂O
B)LiAlH₄/ether,then H₃O⁺
C)PCC/CH₂Cl₂
D)Zn,H₃O⁺
E)H₂,Pt

Question 30

Which product is formed from the following transformation:

A)

B)

C)

D)

E)

Question 31

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CHO into CH₃CH₂CH=CHCH₂CH₂CH₂OH?

A)KMnO₄
B)NaBH₄
C)Br₂ in CCl₄
D)H₂,Ni
E)Two of these choices.

Question 32

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CH₂OH into CH₃CH₂CH=CHCH₂CH₂CHO?

A)KMnO₄(aq,alkaline)
B)CrO₃ / H₂SO₄
C)PCC in CH₂Cl₂
D)Br₂,CCl₄
E)Two of these choices.

Question 33

The following transformation would be considered a(n)?

A)reduction
B)oxidation
C)addition
D)elimination
E)rearrangement

Question 34

Which of these compounds cannot be reduced by sodium borohydride?

A)
B)
C)
D)
E)Two of these choices cannot be reduced.

Question 35

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂C≡CCH₂CH₂CHO into CH₃CH₂C≡CCH₂CH₂CH₂OH?

A)KMnO₄
B)NaBH₄
C)Br₂ in CCl₄
D)H₂,Ni
E)Two of these choices.

Question 36

The following transformation would be considered a(n)?

A)reduction
B)oxidation
C)addition
D)elimination
E)rearrangement

Question 37

Which reagent(s)is/are capable of reducing the following ester to a primary alcohol?

A)LiAlH₄ / ether
B)NaBH₄ / H₂O
C)Na / C₂H₅OH
D)H₂ / Ni,atmospheric pressure
E)All can be used successfully.

Question 38

Which of the reagents listed below would efficiently accomplish the transformation of CH₃CH₂CH=CHCH₂CH₂CH₂OH into CH₃CH₂CH=CHCH₂CH₂CHO?

A)KMnO₄,OH^-
B)CrO₃ / H₂SO₄
C)(i)(COCl)₂,DMSO,-60 ^oC,(ii)Et₃N
D)Br₂,CCl₄
E)Two of these choices.

Question 39

Which of the reagents listed below would efficiently accomplish the transformation of 2-methyl-3-cyclopentenol into 2-methyl-3-cyclopentenone?

A)KMnO₄(aq,alkaline)
B)CrO₃/H₂SO₄
C)H₂,Pt
D)Br₂,CCl₄
E)Two of these choices.

Question 40

Which of the reagents listed below would efficiently accomplish the transformation of ethyl-3-pentenoate into 3-penten-1-ol?

A)i)LiAlH₄; ii)H₂O
B)NaBH₄,H₂O
C)H₂,Pd
D)Two of these choices.
E)All of these choices.

Question 41

What would be the product,A,of the following reaction sequence?

A)CH₃CH₂CH₂CH₃
B)
C)
D)CH₃CH₂CH₂CH₂OD
E)CH₃CH₂CH₂CH₂D

Question 42

Your task is to synthesize through a Grignard synthesis.Which pairs of compounds listed below would you choose as starting materials?

A)
B)
C)
D)
E)None of these choices.

Question 43

What is the major product from the reaction of 2-hexanol with H₂CrO₄?

A)CH₃CO₂H
B)CH₃(CH₂)₃CO₂H
C)
D)CH₃(CH₂)₄CO₂H
E)Two of these choices.

Question 44

Which method would give

A)
B)
C)
D)More than one of these choices.
E)None of these choices.

Question 45

Which reaction leads to an optically active product?

A)
B)
C)
D)
E)

Question 46

Which reagent(s)is/are capable of reducing the following ester to an aldehyde?

A)LiAlH₄ / ether
B)NaBH₄ / H₂O
C)Na / C₂H₅OH
D)H₂ / Ni,atmospheric pressure
E)None of these choices can be used successfully.

Question 47

What would be the product,O,of the following reaction sequence?

A)CH₃CH₂CH₂CH₃
B)
C)
D)CH₃CH₂CH₂CH₂OD
E)CH₃CH₂CH₂CH₂D

Question 48

Which product is formed from the following transformation:

A)

B)

C)

D)

E)None of these choices.

Question 49

What is the major product from the reaction of toluene with KMnO₄?

A)
B)
C)
D)
E)

Question 50

What is the major product from the reaction of 2-hexanol with PCC in CH₂Cl₂?

A)CH₃CO₂H
B)CH₃(CH₂)₃CO₂H
C)
D)CH₃(CH₂)₄CO₂H
E)Two of these choices.

Question 51

Which of the following synthetic procedures would be employed most effectively to transform ethanol into ethyl propyl ether?

A)Ethanol + HBr,then Mg/ether,then H₃O⁺,then NaH,then CH₃CH₂Br
B)Ethanol + HBr,then Mg/ether,then HCHO,then H₃O⁺,then NaH,then CH₃CH₂Br
C)Ethanol + CH₃CH₂CH₂OH + H₂SO₄/140 ^$\circ$ C
D)Ethanol + NaH,then HCHO,then H₃O⁺,then HBr,then Mg/ether,then CH₃CH₂CH₂Br
E)Ethanol + H₂SO₄/180 °C,then CH₃CH₂CH₂Br

Question 52

Your task is to synthesize through a Grignard synthesis.Which pairs of compounds listed below would you choose as starting materials?

A)
B)
C)
D)More than one of these choices.
E)None of these choices.

Question 53

What would be the product,A,of the following reaction?

A)
B)
C)
D)
E)

Question 54

How could the following synthesis be accomplished?

A)(1)SOCl₂,(2)Mg,ether,(3) then H₃O⁺
B)(1)SOCl₂,(2)Li,ether,(3)(CH₃CH₂)₂CuLi,(4)KMnO₄,OH^-
C)1)PBr₃,(2)Mg,ether,(3) then H₃O⁺ (4)PCC,CH₂Cl₂
D)More than one of these choices.
E)None of these choices.

Question 55

What is the principal product(s)formed when 1 mol of methylmagnesium iodide reacts with 1 mol of p-hydroxyacetophenone?

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

Question 56

What is the major product from the reaction of 2-hexanol with Na₂Cr₂O₇/H⁺?

A)CH₃CO₂H
B)CH₃(CH₂)₃CO₂H
C)
D)CH₃(CH₂)₄CO₂H
E)Two of these choices.

Question 57

What compound(s)result(s)from the reaction of CH₃CH₂CH₂MgBr with CH₃CH₂CH₂CH₂CO₂H (1:1 mole ratio)?

A)
B)
C)
D)CH₃CH₂CH₃ + CH₃CH₂CH₂CH₂CO₂MgBr
E)

Question 58

What is the major product from the reaction of 2-hexanol with KMnO₄?

A)CH₃CO₂H
B)CH₃(CH₂)₃CO₂H
C)
D)CH₃(CH₂)₄CO₂H
E)Two of these choices.

Question 59

What is the principal product(s)formed when 1 mol of methylmagnesium iodide reacts with 1 mol of p-acetylbenzoic acid?

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

Question 60

What would be the product,A,of the following reaction sequence?

A)CH₃CH₂CH₂CH₃
B)
C)
D)CH₃CH₂CH₂CH₂OD
E)CH₃CH₂CH₂CH₂D

Question 61

What is the principal product of the following reaction: + CH₃CH₂CH₂CH₂MgBr/ether; then H₂O $\to$ ?

A)
B)
C)
D)
E)

Question 62

What is (are)the principal product(s)formed when 1 mol of ethylmagnesium bromide reacts with 1 mol of 3-(N-methylamino)cyclopentanone?

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

Question 63

Predict the product(s)of the following reaction:

A)A mixture of I and II
B)A mixture of I and III
C)A mixture of II and III
D)A mixture of II and IV
E)A mixture of III and IV

Question 64

What is the product,A,that would be obtained from the following reaction sequence?

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

Question 65

What would be the final product,D,in the following reaction sequence?

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

Question 66

The final product,D,in the following reaction sequence , would be:

A)
B)
C)
D)
E)

Question 67

The final product,B,in the following reaction sequence, ,would be?

A)
B)
C)
D)
E)

Question 68

When 1-pentanol is treated with alkaline potassium permanganate,

A)the color changes from orange to blue.
B)the color changes from purple to colorless.
C)the color changes from blue to red.
D)the color changes from orange to green.
E)the color changes from green to orange.

Question 69

What would be the final product,D,in the following reaction sequence?

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

Question 70

What is the product,A,that would be obtained from the following reaction sequence?

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

Question 71

What is the product,A,that would be obtained from the following reaction sequence?

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

Question 72

The final product,B,in the following reaction sequence, ,would be?

A)
B)
C)
D)
E)NNone of these choices.

Question 73

What would be the product,A,of the following reaction sequence?

A)CH₃CH₂CH₂CH₃
B)
C)
D)CH₃CH₂CH₂CH₂OD
E)CH₃CH₂CH₂CH₂D

Question 74

Predict the product(s)of the following reaction:

A)A mixture of I and II
B)A mixture of I and III
C)A mixture of II and III
D)A mixture of II and IV
E)A mixture of III and IV

Question 75

What product(s)is/are formed in the following reaction?

A)CH₃CH₂CH₂CH₂OD + CH₃CH₂OD
B)CH₃CH₂CH₂CD₂OD + CH₃CH₂OD
C)CH₃CH₂CH₂CD₂OH + CH₃CH₂OH
D)CH₃CH₂CH₂CHDOD + CH₃CH₂OD
E)

Question 76

What would be the final product,A,in the following reaction sequence?

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

Question 77

.Predict the product(s)of the following reaction:

A)I
B)II
C)III
D)IV
E)A mixture of two or more of these choices.

Question 78

The final product,D,in the following reaction sequence, ,would be?

A)
B)
C)
D)
E)

Question 79

What would be the final product,A,in the following reaction sequence?

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

Question 80

Predict the product(s)of the following reaction:

A)A mixture of I and II
B)A mixture of I and III
C)A mixture of II and III
D)A mixture of II and IV
E)A mixture of III and IV