Question 1

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 2

Arrange the following compounds in order of increasing acidity:
acetone, ethyl acetoacetate, ethyl acetate, and ethanol.

Accepted Answer

ethyl acetate < acet

Question 3

What is the approximate pKa of diethyl malonate?

Accepted Answer

A)  45 
B)  20 
C)  13 
D)  10 
E)  4 
A)  45 
B)  20 
C)  13 
D)  10 
E)  4

Question 4

When a ketone and its enol are in equilibrium, under most conditions the concentration of the enol is ________ the concentration of the ketone.

Accepted Answer

A)  slightly higher than 
B)  equal to 
C)  much higher than 
D)  much lower than 
E)  exactly half of 
A)  slightly higher than 
B)  equal to 
C)  much higher than 
D)  much lower than 
E)  exactly half of

Question 5

For the equilibrium shown below, is the Keq greater or less than 1?

Accepted Answer

Question 6

Provide a synthesis of the compound shown below from cyclopent-2-en-1-one and acetoacetic ester.

Accepted Answer

From acetoacetic est

Question 7

Provide a mechanism for the following reaction:
butanoic acid + Br2 + PBr3 → 2-bromobutanoyl bromide

Accepted Answer

Question 8

What product results when an aldol is dehydrated?

Accepted Answer

A)  conjugated alkyne 
B)  β-diketone 
C)  β-ketoester 
D)  α,β-unsaturated aldehyde 
E)  β,γ-unsaturated aldehyde 
A)  conjugated alkyne 
B)  β-diketone 
C)  β-ketoester 
D)  α,β-unsaturated aldehyde 
E)  β,γ-unsaturated aldehyde

Question 9

Provide the structure of the major organic product which results when PhCO2CH2CH3 and CH3CH2CO2CH2CH3 are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Accepted Answer

Question 10

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

1) diethyl

Question 11

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 12

Which of the following is most acidic?

Accepted Answer

A)  acetone 
B)  ethyl acetate 
C)  malonic ester 
D)  acetoacetic ester 
E)  acetaldehyde 
A)  acetone 
B)  ethyl acetate 
C)  malonic ester 
D)  acetoacetic ester 
E)  acetaldehyde

Question 13

What type of product results when 3-pentanone reacts with dimethylamine?

Accepted Answer

A)  enolate 
B)  enol 
C)  amide 
D)  imine 
E)  enamine 
A)  enolate 
B)  enol 
C)  amide 
D)  imine 
E)  enamine

Question 14

What species results when cyclopentanone is treated with lithium diisopropylamide at low temperature?

Accepted Answer

the lithiu

Question 15

For the equilibrium shown below, is the Keq greater or less than 1?

Accepted Answer

Question 16

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 17

Provide the structure of the aldol product that results when 5-methylhexanal is treated with hydroxide.

Accepted Answer

The answer of Provide the structure of the aldol product...

Question 18

Provide the sequence of steps necessary to synthesize the compound shown below from cyclohexene.

Accepted Answer

1. O₃ 2. S(

Question 19

Predict the structure of the expected product of the following reaction.

Accepted Answer

The answer of Predict the structure of the expected product...

Question 20

Provide a detailed, stepwise mechanism for the Robinson annulation reaction between 2-methylcyclohexanone and methyl vinyl ketone.

Accepted Answer

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

Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Provide the major organic product of the reaction shown below.

Arrange the following compounds in order of increasing acidity: acetone, ethyl acetoacetate, ethyl acetate, and ethanol.

What is the approximate pKa of diethyl malonate?

When a ketone and its enol are in equilibrium, under most conditions the concentration of the enol is ________ the concentration of the ketone.

For the equilibrium shown below, is the Keq greater or less than 1?

Provide a synthesis of the compound shown below from cyclopent-2-en-1-one and acetoacetic ester.

Provide a mechanism for the following reaction: butanoic acid + Br2 + PBr3 → 2-bromobutanoyl bromide

What product results when an aldol is dehydrated?

Provide the structure of the major organic product which results when PhCO2CH2CH3 and CH3CH2CO2CH2CH3 are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Complete the following reaction by filling in the necessary reagents.

Provide the major organic product of the following reaction.

Which of the following is most acidic?

What type of product results when 3-pentanone reacts with dimethylamine?

What species results when cyclopentanone is treated with lithium diisopropylamide at low temperature?

For the equilibrium shown below, is the Keq greater or less than 1?

Provide the major organic product of the following reaction.

Provide the structure of the aldol product that results when 5-methylhexanal is treated with hydroxide.

Provide the sequence of steps necessary to synthesize the compound shown below from cyclohexene.

Predict the structure of the expected product of the following reaction.

Provide a detailed, stepwise mechanism for the Robinson annulation reaction between 2-methylcyclohexanone and methyl vinyl ketone.

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

For the equilibrium shown below, is the K_eq greater or less than 1?

Provide a mechanism for the following reaction: butanoic acid + Br₂ + PBr₃ → 2-bromobutanoyl bromide

Provide the structure of the major organic product which results when PhCO₂CH₂CH₃ and CH₃CH₂CO₂CH₂CH₃ are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

For the equilibrium shown below, is the K_eq greater or less than 1?