Deck 12: Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Question 1

Which reaction is an oxidation?

A) RCHO $\rightarrow$ RCO₂H
B) RCH₂OH F $\rightarrow$ RCHO
C) RCH₂OH $\rightarrow$ RCO₂H
D) None of these
E) All of these

Answer 1

All of these

Question 2

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.

Answer 2

LiAlH₄ / ether

Question 3

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 the above can be used successfully.

Answer 3

None of the above can be used successfully.

Question 4

The following transformation would be considered a(n)?

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

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

Question 7

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 8

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 9

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 10

Which of these transformations cannot be classified as a reduction?

A) RCH₂Cl $\rightarrow$ RCH₃
B) RCH=CH₂ $\rightarrow$ RCH₂CH₃
C) RCOOH $\rightarrow$ RCH₂OH
D)

E) All of these are reductions.

Question 11

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 12

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 13

The following transformation would be considered a(n)?

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

Question 14

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 15

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

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

Question 16

Which of these compounds will not be reduced by LiAlH₄?

A) CH₃CH₂CH₂CH=CH₂
B)

C)

D)

E)

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

Question 19

The following transformation would be considered a(n)?

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

Question 20

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 21

Which of the reagents/techniques listed below would serve as the basis for a simple chemical test to distinguish between 2-methyl-3-hexyn-1-ol and 2-methyl-5-hexyn-1-ol?

A) CrO₃ in H₂SO₄
B) Cold conc.H₂SO₄
C) Br₂ in CCl₄
D) NaBH₄
E) IR spectroscopy

Question 22

What would be the major product of the following reaction?

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

Question 23

When 2-pentanol is treated with chromic acid,

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 24

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 the above

Question 25

Fundamentally,2-methyl-2-pentanol does not undergo oxidation by H₂CrO₄ because:

A) the intermediate chromate ester is not formed.
B) the oxidant isn't in a sufficiently high oxidation state.
C) the alcohol undergoes dehydration.
D) the intermediate chromate ester cannot lose hydrogen.
E) Actually,this oxidation does occur.

Question 26

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

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

Question 27

Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between CH₃CH=CHCH₃ and CH₃CHOHCH₂CH₃?

A) CrO₃ in H₂SO₄
B) KMnO₄
C) Br₂ in CCl₄
D) Two of these
E) All of these

Question 28

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 29

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 the above

Question 30

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

A)

B)

C)

D)

E)

Question 31

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 32

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between CH₃CH=CHCH₂OH and CH₃CH₂CH₂CH₂OH ?

A) CrO₃ in H₂SO₄
B) Cold conc.H₂SO₄
C) Br₂ in CCl₄
D) NaOH/H₂O
E) NaBH₄

Question 33

If the role of the solvent is to assist in the preparation and stabilization of the Grignard reagent by coordination with the magnesium,which of these solvents should be least effective?

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

Question 34

Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH₃)₃COH and (CH₃)₂CHCH₂OH ?

A) NaH
B) NaOH/H₂O
C) Br₂ in CCl₄
D) Cold conc.H₂SO₄
E) CrO₃ in H₂SO₄

Question 35

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 36

Consider the molecule Which reagent will not give a positive test with this compound?

A) Cold conc.H₂SO₄
B) Br₂/CCl₄
C) NaOH (aq)
D) CrO₃/H₂SO₄
E) Dilute KMnO₄/H₂O

Question 37

Which of these is the least reactive type of organometallic compound?

A) RK
B) R₂Hg
C) RLi
D) R₂Zn
E) R₃Al

Question 38

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 39

When 3-methyl-3-pentanol is treated with chromic acid,

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

Question 40

CrO₃ in H₂SO₄/H₂O will fail to give a positive test with which of these compounds?

A) CH₃CH₂CH₂CH₂OH
B)

C) (CH₃)₃COH
D)

E) More than one of these

Question 41

What is the final product of the following reaction sequence?

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

Question 42

Grignard reagents react with oxirane (ethylene oxide)to form 1 $\degree$ alcohols but can be prepared in tetrahydrofuran solvent.Why is this difference in behavior observed?

A) Steric hindrance in the case of tetrahydrofuran precludes reaction with the Grignard.
B) There is a better leaving group in the oxirane molecule.
C) The oxirane ring is the more highly strained.
D) It is easier to obtain tetrahydrofuran in anhydrous condition.
E) Oxirane is a cyclic ether,while tetrahydrofuran is a hydrocarbon.

Question 43

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 44

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

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

Question 45

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

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

Question 46

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

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 47

Which of these reactions will not produce a 1 $\degree$ alcohol?

A)

B)

C)

D)

E)

Question 48

The final product,E,in the following reaction sequence is,

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

Question 49

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

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 50

The final product,E,in the following reaction sequence is,

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

Question 51

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

A)

B)

C)

D)

E)

Question 52

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

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 53

What product(s)is/are produced in the 1:1 reaction of sec-butylmagnesium bromide with

A)

B)

C)

D)

E)

Question 54

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 55

Which of the following would serve as a synthesis of racemic 2-methyl-1-phenyl-2-butanol?

A) I
B) II
C) III
D) All of the above
E) None of the above

Question 56

Which synthesis of a Grignard reagent would fail to occur as written?

A)

B)

C)

D)

E) All of the above will succeed.

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

A) CH₃CH₂CH₂CH₃
B)

C)

D) CH₃CH₂CH₂CH₂OD
E) CH₃CH₂CH₂CH₂D

Question 59

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

A) CH₃CH₂CH₂CH₃
B)

C)

D) CH₃CH₂CH₂CH₂OD
E) CH₃CH₂CH₂CH₂D

Question 60

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 61

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

Question 62

What is the final product?

A)

B)

C)

D)

E) None of these

Question 63

Which reaction leads to an optically active product?

A)

B)

C)

D)

E)

Question 64

Which of the following is the strongest base?

A) RMgX
B) Mg(OH)X
C) RH
D) H₂O

Question 65

Which of these compounds can be used to prepare the corresponding Grignard reagent?

A) CH₃CHOHCH₂CH₂CH₂CH₂Br
B) (CH₃)₃CHCHBrCH₂CH₂CO₂H
C) BrCH=CHCH₂CH₂CH₃
D) CH₃NHCH₂CH₂Br
E) None of the above can be used to prepare the corresponding Grignard reagent.

Question 66

What is/are the principal product(s)formed when excess methylmagnesium iodide reacts with p-hydroxyacetophenone ?

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

Question 67

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
E) None of these

Question 68

Which method would give

A)

B)

C)

D) More than one of the above
E) None of the above

Question 69

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 70

In which of the following series are the compounds arranged in order of decreasing basicity?

A) CH₃CH₂MgBr > NaNH₂ > HC $\equiv$ CNa > NaOH > CH₃CH₂ONa
B) CH₃CH₂MgBr > NaNH₂ > HC $\equiv$ CNa > CH₃CH₂ONa > NaOH
C) HC $\equiv$ CNa > CH₃CH₂MgBr > NaNH₂ > CH₃CH₂ONa > NaOH
D) NaNH₂ > CH₃CH₂MgBr > HC $\equiv$ CNa > CH₃CH₂ONa > NaOH
E) None of these

Question 71

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 the above
E) None of the above

Question 72

Which of these compounds cannot be used to prepare the corresponding Grignard reagent?

A) CH₃OCH₂CH₂CH₂Br
B) (CH₃)₃CCl
C) CH₂=CHCH₂Br
D) (CH₃)₂NCH₂CH₂Br
E)

Question 73

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 74

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 75

What is/are the principal product(s)formed when excess methylmagnesium iodide reacts with p-hydroxyacetophenone ?

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

Question 76

What is the product,A,that would be obtained from the following reaction sequence? NaNH₂

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

Question 77

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 $\degree$ C
D) Ethanol + NaH,then HCHO,then H₃O⁺,then HBr,then Mg/ether,then CH₃CH₂CH₂Br
E) Ethanol + H₂SO₄/180°C,then CH₃CH₂CH₂Br

Question 78

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

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

Question 79

What is/are the principal product(s)formed when excess methylmagnesium iodide reacts with p-hydroxyacetophenone ?

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

Question 80

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

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