Question 1

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

Accepted Answer

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 S1U1P1$\circ$S1S1P0C 
D) Ethanol + NaH,then HCHO,then H3O+,then HBr,then Mg/ether,then CH3CH2CH2Br 
E) Ethanol + H2SO4/180 °C,then CH3CH2CH2Br 
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 S1U1P1$\circ$S1S1P0C 
D) Ethanol + NaH,then HCHO,then H3O+,then HBr,then Mg/ether,then CH3CH2CH2Br 
E) Ethanol + H2SO4/180 °C,then CH3CH2CH2Br

Question 2

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 3

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 4

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?

Accepted Answer

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

Question 5

What would be the final product,A,in 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 6

What is/are the principal product(s)formed when excess methylmagnesium iodide reacts with 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 7

Predict the product D of the following reaction sequence:

Accepted Answer

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

Question 8

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

Accepted Answer

A) 2,6-Dimethylheptane 
B) 2,2-Dimethylpropane 
C) 2-Methylpentane 
D) 2,2,5-Trimethylhexane 
E) 2,2,6-Trimethylheptane 
A) 2,6-Dimethylheptane 
B) 2,2-Dimethylpropane 
C) 2-Methylpentane 
D) 2,2,5-Trimethylhexane 
E) 2,2,6-Trimethylheptane

Question 9

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

Accepted Answer

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

Question 10

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

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 11

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 12

Predict the product(s)of the following reaction:

Accepted Answer

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 
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 13

Which of the following molecules,if any,contains a prochiral carbon?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices.

Question 14

LAH is the abbreviation for the powerful reducing agent ___.

Accepted Answer

lithium al

Question 15

Compounds that contain carbon-metal bonds are known as ___.

Accepted Answer

organometa

Question 16

When 2-pentanol is treated with chromic acid,

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 17

Why can we not prepare a Grignard reagent from a molecule such as 4-bromo-1-butanol?

Accepted Answer

Because Grignard reagents are extremely

Question 18

The process of converting an alkyl halide to an alkane using LAH is a(n)___ reaction.

Accepted Answer

The answer of The process of converting an alkyl halide...

Question 19

Suggest a reasonable synthetic strategy for the synthesis of 3-ethyl-3-heptanol from pentanoic acid,CH3CH2CH2CH2CO2H.

Accepted Answer

CH₃CH₂CH₂

Question 20

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

Accepted Answer

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

Exam 12: Alcohols From Carbonyl Compounds

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

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

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

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?

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

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

Predict the product D of the following reaction sequence:

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

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

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

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

Predict the product(s)of the following reaction:

Which of the following molecules,if any,contains a prochiral carbon?

LAH is the abbreviation for the powerful reducing agent ___.

Compounds that contain carbon-metal bonds are known as ___.

When 2-pentanol is treated with chromic acid,

Why can we not prepare a Grignard reagent from a molecule such as 4-bromo-1-butanol?

The process of converting an alkyl halide to an alkane using LAH is a(n)___ reaction.

Suggest a reasonable synthetic strategy for the synthesis of 3-ethyl-3-heptanol from pentanoic acid,CH3CH2CH2CH2CO2H.

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

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 CH₃CH₂CH=CHCH₂CH₂CH₂OH into CH₃CH₂CH=CHCH₂CH₂CHO?

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

Suggest a reasonable synthetic strategy for the synthesis of 3-ethyl-3-heptanol from pentanoic acid,CH₃CH₂CH₂CH₂CO₂H.