Question 1

Disregarding stereoisomers, how many different enols can phenylacetone form?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  4 
A)  0 
B)  1 
C)  2 
D)  3 
E)  4

Question 2

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 3

Why is the acid-catalyzed halogenation of ketones generally preferred over the base-promoted halogenation?

Accepted Answer

Multiple halogenatio

Question 4

Provide a detailed, stepwise mechanism for the a-bromination of acetone in base.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 5

The aldol condensation is:

Accepted Answer

A)  an irreversible reaction. 
B)  an equilibrium reaction. 
C)  a tautomerization. 
D)  an isomerization. 
E)  a type of esterification. 
A)  an irreversible reaction. 
B)  an equilibrium reaction. 
C)  a tautomerization. 
D)  an isomerization. 
E)  a type of esterification.

Question 6

Provide the sequence of reagents needed to convert CH3CH2O2CCH2COCH3 to 7-methyl-2-octanone.

Accepted Answer

1. NaOCH₂CH

Question 7

Which of the following compounds will not undergo reaction with an enolate?

Accepted Answer

A)  1-pentene 
B)  bromine 
C)  propanal 
D)  1-bromobutane 
E)  benzoyl chloride 
A)  1-pentene 
B)  bromine 
C)  propanal 
D)  1-bromobutane 
E)  benzoyl chloride

Question 8

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 9

What additional starting material is needed to complete the following transformation?

Accepted Answer

The answer of What additional starting material is needed to...

Question 10

Draw the major organic product resulting from the reaction conditions shown below.

Accepted Answer

The answer of Draw the major organic product resulting from...

Question 11

Which of the following is least likely to undergo a smooth crossed Claisen condensation with methyl pentanoate?

Accepted Answer

A)  (CH3)3CCO2CH3 
B)  PhCH2CO2CH3 
C)  PhCO2CH3 
D)  HCO2CH3 
E)  (CH3O)2CO 
A)  (CH3)3CCO2CH3 
B)  PhCH2CO2CH3 
C)  PhCO2CH3 
D)  HCO2CH3 
E)  (CH3O)2CO

Question 12

Which of the following is another name for the product of an aldol condensation?

Accepted Answer

A)  β-hydroxyaldehyde 
B)  α-hydroxyaldehyde 
C)  acetal 
D)  β-ketoester 
E)  1,3-dialdehyde 
A)  β-hydroxyaldehyde 
B)  α-hydroxyaldehyde 
C)  acetal 
D)  β-ketoester 
E)  1,3-dialdehyde

Question 13

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 14

Which of the following could result from the dehydration of a self-aldol condensation product?

Accepted Answer

A)  4-methyl-3-penten-2-one 
B)  4-methyl-4-penten-2-one 
C)  4-methyl-5-hexen-2-one 
D)  4-methyl-4-hexen-2-one 
E)  3-methyl-4-penten-2-one 
A)  4-methyl-3-penten-2-one 
B)  4-methyl-4-penten-2-one 
C)  4-methyl-5-hexen-2-one 
D)  4-methyl-4-hexen-2-one 
E)  3-methyl-4-penten-2-one

Question 15

Provide the structure of the product of the crossed Claisen condensation between PhCO2CH2CH3 and CH3CH2CO2CH2CH3.

Accepted Answer

Question 16

Provide a detailed, stepwise mechanism for the transformation shown below.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 17

Provide the structure of the more stable enol tautomer of 1-phenyl-2-octanone.

Accepted Answer

The answer of Provide the structure of the more stable...

Question 18

Provide the sequence of reagents needed to convert (CH3CH2O2C)2CH2 to heptanoic acid.

Accepted Answer

1. NaOCH₂CH

Question 19

What compound is produced in the reaction of cyclopentanone with Br2 in acetic acid?

Accepted Answer

2-bromocyc

Question 20

Predict the pKa unit of the indicated proton within +/- 1 pKa unit.

Accepted Answer

A)  5 
B)  11 
C)  19 
D)  24 
A)  5 
B)  11 
C)  19 
D)  24

Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Disregarding stereoisomers, how many different enols can phenylacetone form?

Provide the major organic product of the reaction shown below.

Why is the acid-catalyzed halogenation of ketones generally preferred over the base-promoted halogenation?

Provide a detailed, stepwise mechanism for the a-bromination of acetone in base.

The aldol condensation is:

Provide the sequence of reagents needed to convert CH3CH2O2CCH2COCH3 to 7-methyl-2-octanone.

Which of the following compounds will not undergo reaction with an enolate?

Provide the major organic product of the following reaction.

What additional starting material is needed to complete the following transformation?

Draw the major organic product resulting from the reaction conditions shown below.

Which of the following is least likely to undergo a smooth crossed Claisen condensation with methyl pentanoate?

Which of the following is another name for the product of an aldol condensation?

Provide the major organic product of the following reaction.

Which of the following could result from the dehydration of a self-aldol condensation product?

Provide the structure of the product of the crossed Claisen condensation between PhCO2CH2CH3 and CH3CH2CO2CH2CH3.

Provide a detailed, stepwise mechanism for the transformation shown below.

Provide the structure of the more stable enol tautomer of 1-phenyl-2-octanone.

Provide the sequence of reagents needed to convert (CH3CH2O2C)2CH2 to heptanoic acid.

What compound is produced in the reaction of cyclopentanone with Br2 in acetic acid?

Predict the pKa unit of the indicated proton within +/- 1 pKa unit.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide the sequence of reagents needed to convert CH₃CH₂O₂CCH₂COCH₃ to 7-methyl-2-octanone.

Provide the structure of the product of the crossed Claisen condensation between PhCO₂CH₂CH₃and CH₃CH₂CO₂CH₂CH₃.

Provide the sequence of reagents needed to convert (CH₃CH₂O₂C)₂CH₂ to heptanoic acid.

What compound is produced in the reaction of cyclopentanone with Br₂ in acetic acid?

Predict the pK_a unit of the indicated proton within +/- 1 pK_a unit.