Question 1

Draw the important resonance forms for the enolate ion/s that are formed when acetophenone reacts with base.

Accepted Answer

The answer of Draw the important resonance forms for the...

Question 2

Consider the reaction shown below. Use pKa values to determine which way the equilibrium lies.

Accepted Answer

The pKa of the α-hydrogen of a

Question 3

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

Accepted Answer

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

Question 4

Provide the major organic product of the reaction shown below.

Accepted Answer

2-acetylcy

Question 5

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 6

Provide a detailed, stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone, hydroxide and iodine.

Accepted Answer

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

Question 7

Name the product which results when ethyl butanoate is treated with sodium ethoxide followed by neutralization.

Accepted Answer

ethyl 2-et

Question 8

The Hell-Volhard-Zelinsky reaction involves ________.

Accepted Answer

A)  the α-bromination of carboxylic acids 
B)  the α-bromination of ketones 
C)  the bromination of alcohols 
D)  the oxidation of aldehydes to acids 
E)  none of the above 
A)  the α-bromination of carboxylic acids 
B)  the α-bromination of ketones 
C)  the bromination of alcohols 
D)  the oxidation of aldehydes to acids 
E)  none of the above

Question 9

Complete the following short synthesis by providing the necessary sequence of reagents.

Accepted Answer

1) I₂ / NaO

Question 10

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

Accepted Answer

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 ketones will give a positive iodoform test?

Accepted Answer

A)  4-heptanone 
B)  3-hexanone 
C)  2-hexanone 
D)  cyclohexanone 
E)  2-methyl-3-pentanone 
A)  4-heptanone 
B)  3-hexanone 
C)  2-hexanone 
D)  cyclohexanone 
E)  2-methyl-3-pentanone

Question 13

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

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

When aldehydes are subjected to the same conditions that α-halogenate ketones (i.e., X2 and aqueous acid or base), they are ________.

Accepted Answer

A)  α-halogenated as well 
B)  reduced to alcohols 
C)  converted to the acid halide 
D)  oxidized to the acid or carboxylate 
E)  esterified 
A)  α-halogenated as well 
B)  reduced to alcohols 
C)  converted to the acid halide 
D)  oxidized to the acid or carboxylate 
E)  esterified

Question 16

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

Accepted Answer

Question 17

The reaction of LDA with acetophenone produces ________.

Accepted Answer

A)  an enol 
B)  an enolate 
C)  an ylide 
D)  alkylation 
E)  halogenation 
A)  an enol 
B)  an enolate 
C)  an ylide 
D)  alkylation 
E)  halogenation

Question 18

In theory a poorly planned crossed aldol reaction can produce how many different products?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 19

Starting with cyclohexene and employing a Dieckmann cyclization show how the compound below can be prepared.

Accepted Answer

1) KMnO₄, ^-OH, Δ 2) H⁺

Question 20

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

Accepted Answer

1) NaOCH₂CH

Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Draw the important resonance forms for the enolate ion/s that are formed when acetophenone reacts with base.

Consider the reaction shown below. Use pKa values to determine which way the equilibrium lies.

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

Provide the major organic product of the reaction shown below.

Provide the major organic product of the following reaction sequence.

Provide a detailed, stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone, hydroxide and iodine.

Name the product which results when ethyl butanoate is treated with sodium ethoxide followed by neutralization.

The Hell-Volhard-Zelinsky reaction involves ________.

Complete the following short synthesis by providing the necessary sequence of reagents.

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

Provide the major organic product of the following reaction.

Which of the following ketones will give a positive iodoform test?

Complete the following reaction by filling in the necessary reagents.

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

When aldehydes are subjected to the same conditions that α-halogenate ketones (i.e., X2 and aqueous acid or base), they are ________.

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

The reaction of LDA with acetophenone produces ________.

In theory a poorly planned crossed aldol reaction can produce how many different products?

Starting with cyclohexene and employing a Dieckmann cyclization show how the compound below can be prepared.

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

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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?

When aldehydes are subjected to the same conditions that α-halogenate ketones (i.e., X₂ and aqueous acid or base), they are ________.

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

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