Question 1

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

Accepted Answer

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

Question 2

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

Accepted Answer

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

Question 3

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

Accepted Answer

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

Question 4

Upon reaction with a primary or secondary alcohol,the change in oxidation state of chromium ion in Jones reagent is from ___ to ___.

Accepted Answer

The answer of Upon reaction with a primary or secondary...

Question 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

A) KMnO4,OH- 
B) CrO3 / H2SO4 
C) PCC in CH2Cl2 
D) (i)(COCl)2,DMSO,-60 oC,(ii)Et3N 
E) Two of these choices. 
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 7

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

Accepted Answer

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

Question 8

Which of the following reactions would serve as a reasonable synthesis of the following racemic alcohol (2-phenyl-2-butanol)?

Accepted Answer

A) 
  
B)    
C)    
D) Two of these choices. 
E) All of these choices. 
A) 
  
B)    
C)    
D) Two of these choices. 
E) All of these choices.

Question 9

Reaction of an alkyllithium with a ketone produces,after acid work-up,a ___ alcohol.

Accepted Answer

The answer of Reaction of an alkyllithium with a ketone...

Question 10

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

Accepted Answer

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

Question 11

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

Accepted Answer

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

Question 12

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

Accepted Answer

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

Question 13

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

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 14

Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH2CH2CH2CHO.

Accepted Answer

Question 15

Which of these transformations cannot be classified as a reduction?

Accepted Answer

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

Question 16

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

Accepted Answer

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

Question 17

PCC and CrO3 are both Cr(VI)reagents.However,PCC/CH2Cl2 is useful in oxidizing primary alcohols to aldehydes,while the analogous reaction with CrO3/H2SO4 will typically produce carboxylic acids.Why?

Accepted Answer

Both reagents first oxidize the alcohol

Question 18

A Grignard reagent will produce a secondary alcohol when reacted with ___.

Accepted Answer

any aldehy

Question 19

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

Accepted Answer

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

Question 20

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

Accepted Answer

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

Exam 12: Alcohols From Carbonyl Compounds

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

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

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

Upon reaction with a primary or secondary alcohol,the change in oxidation state of chromium ion in Jones reagent is from ___ to ___.

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

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

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

Which of the following reactions would serve as a reasonable synthesis of the following racemic alcohol (2-phenyl-2-butanol)?

Reaction of an alkyllithium with a ketone produces,after acid work-up,a ___ alcohol.

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

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

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

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

Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH2CH2CH2CHO.

Which of these transformations cannot be classified as a reduction?

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

PCC and CrO3 are both Cr(VI)reagents.However,PCC/CH2Cl2 is useful in oxidizing primary alcohols to aldehydes,while the analogous reaction with CrO3/H2SO4 will typically produce carboxylic acids.Why?

A Grignard reagent will produce a secondary alcohol when reacted with ___.

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

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

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

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

Upon reaction with a primary or secondary alcohol,the change in oxidation state of chromium ion in Jones reagent is from _ to _.

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

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

Suggest a reasonable synthetic strategy for the synthesis of 1,4-pentanediol from 4-hydroxybutanal HOCH₂CH₂CH₂CHO.

PCC and CrO₃ are both Cr(VI)reagents.However,PCC/CH₂Cl₂ is useful in oxidizing primary alcohols to aldehydes,while the analogous reaction with CrO₃/H₂SO₄ will typically produce carboxylic acids.Why?

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