Question 1

In the reaction of carbonyl compounds with NaBH4,the effective reducing species is:

Accepted Answer

H <sup>-</

Question 2

For the aldehyde shown,indicate on the appropriate arrow which face is the re face,and which face is si?

Accepted Answer

The answer of For the aldehyde shown,indicate on the appropriate...

Question 3

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

Accepted Answer

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

Question 4

Predict the product D of the following reaction sequence:

Accepted Answer

The answer of Predict the product D of the following...

Question 5

What would be the major product of the following reaction?

Accepted Answer

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

Question 6

When 1-pentanol is treated with alkaline potassium permanganate,

Accepted Answer

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. 
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 7

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

Accepted Answer

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

Question 8

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

Accepted Answer

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

Question 9

Which of these compounds will not be reduced by LiAlH4?

Accepted Answer

A)  CH3CH2CH2CH=CH2 
B) 
  
C) 
  
D) 
  
E) 
  
A)  CH3CH2CH2CH=CH2 
B) 
  
C) 
  
D) 
  
E)

Question 10

The reaction of lithium diethylcuprate with 1-bromo-4,4-dimethylhexane yields:

Accepted Answer

A)  3,3-Dimethylheptane 
B)  3,3-Dimethyloctane 
C)  1-Ethyl-4,4-dimethylhexane 
D)  Di-4,4-dimethylhexylcuprate 
E)  None of the above 
A)  3,3-Dimethylheptane 
B)  3,3-Dimethyloctane 
C)  1-Ethyl-4,4-dimethylhexane 
D)  Di-4,4-dimethylhexylcuprate 
E)  None of the above

Question 11

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 12

Suggest a reasonable synthetic strategy for the synthesis of 4-heptanol from 1-pentene.

Accepted Answer

1-pentene @#LAT-DLM&i)MCPBA;ii)CH<sub>3<

Question 13

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

Accepted Answer

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

Question 14

Which of these reduction reactions is unsuccessful?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of these are successful reductions. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of these are successful reductions.

Question 15

Reaction of excess ethyl magnesium iodide with an ethyl acetate (CH3CO2C2H5)produces,after acid work-up,____________ .

Accepted Answer

3-methyl-3

Question 16

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

Accepted Answer

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

Question 17

Draw the resonance structures that account for esters being less reactive toward NaBH4 than aldehydes or ketones.

Accepted Answer

Question 18

The reactivity of organometallic compounds increases with the _____________ of the carbon-metal bond.

Accepted Answer

percent io

Question 19

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

Accepted Answer

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

Question 20

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

Accepted Answer

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

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

In the reaction of carbonyl compounds with NaBH4,the effective reducing species is:

For the aldehyde shown,indicate on the appropriate arrow which face is the re face,and which face is si?

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

Predict the product D of the following reaction sequence:

What would be the major product of the following reaction?

When 1-pentanol is treated with alkaline potassium permanganate,

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

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

Which of these compounds will not be reduced by LiAlH4?

The reaction of lithium diethylcuprate with 1-bromo-4,4-dimethylhexane yields:

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

Suggest a reasonable synthetic strategy for the synthesis of 4-heptanol from 1-pentene.

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

Which of these reduction reactions is unsuccessful?

Reaction of excess ethyl magnesium iodide with an ethyl acetate (CH3CO2C2H5)produces,after acid work-up,____________ .

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

Draw the resonance structures that account for esters being less reactive toward NaBH4 than aldehydes or ketones.

The reactivity of organometallic compounds increases with the _____________ of the carbon-metal bond.

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

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

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

In the reaction of carbonyl compounds with NaBH₄,the effective reducing species is:

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

Which of these compounds will not be reduced by LiAlH₄?

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

Reaction of excess ethyl magnesium iodide with an ethyl acetate (CH₃CO₂C₂H₅)produces,after acid work-up,____________ .

Draw the resonance structures that account for esters being less reactive toward NaBH₄ than aldehydes or ketones.