Question 1

Provide a detailed, stepwise mechanism for the reaction of   
with ammonia.

Accepted Answer

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

Question 2

Provide the proper IUPAC name for the compound below.

Accepted Answer

3,3-dimeth

Question 3

While the carbonyl stretching frequency for simple aldeydes, ketones, and carboxylic acids is about 1710 cm-1, the carbonyl stretching frequency for esters is about ________.

Accepted Answer

A)  1660 cm-1 
B)  1700 cm-1 
C)  1735 cm-1 
D)  1800 cm-1 
E)  2200 cm-1 
A)  1660 cm-1 
B)  1700 cm-1 
C)  1735 cm-1 
D)  1800 cm-1 
E)  2200 cm-1

Question 4

Provide the name of the compound shown below.

Accepted Answer

The answer of Provide the name of the compound shown...

Question 5

Explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in SN2 reactions.

Accepted Answer

In nucleophilic acyl substitution, the l

Question 6

Which sequence ranks the following carboxylic acid derivatives in order of increasing rate of hydrolysis?

Accepted Answer

A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2 
A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2

Question 7

Predict the major organic product in the following reaction.

Accepted Answer

The answer of Predict the major organic product in the...

Question 8

Which of the following is the most reactive carboxylic acid derivative?

Accepted Answer

A)  ester 
B)  anhydride 
C)  nitrile 
D)  acid chloride 
E)  amide 
A)  ester 
B)  anhydride 
C)  nitrile 
D)  acid chloride 
E)  amide

Question 9

Identify the correct IUPAC systematic name for the structure below.

Accepted Answer

A)  N-methyl-2-ethyl-5-methyloctanamide 
B)  6,N-dimethylnonane-3-carboxamide 
C)  5,N-dimethyl-2-ethyloctanamide 
D)  2-ethyl-5,N-dimethyloctanamide 
A)  N-methyl-2-ethyl-5-methyloctanamide 
B)  6,N-dimethylnonane-3-carboxamide 
C)  5,N-dimethyl-2-ethyloctanamide 
D)  2-ethyl-5,N-dimethyloctanamide

Question 10

Amides are less basic than amines because ________.

Accepted Answer

A)  the carbonyl group donates electrons by resonance 
B)  the carbonyl group withdraws electrons by resonance 
C)  the nitrogen does not have a lone pair of electrons 
D)  the nitrogen has a full positive charge 
E)  amides do not contain nitrogen 
A)  the carbonyl group donates electrons by resonance 
B)  the carbonyl group withdraws electrons by resonance 
C)  the nitrogen does not have a lone pair of electrons 
D)  the nitrogen has a full positive charge 
E)  amides do not contain nitrogen

Question 11

Provide the proper IUPAC name for NCCH2CH2CH2CH2CO2CH3.

Accepted Answer

methyl 5-c

Question 12

Which of the following reagents convert(s) benzoyl chloride to phenyl propyl ketone?

Accepted Answer

A)  CH3CH2CH2MgBr 
B)  CH3CH2CH2Li 
C)  (CH3CH2CH2)2CuLi 
D)  both A and B 
E)  both A and C 
A)  CH3CH2CH2MgBr 
B)  CH3CH2CH2Li 
C)  (CH3CH2CH2)2CuLi 
D)  both A and B 
E)  both A and C

Question 13

Provide the proper IUPAC name for ClCH2CH2CONHCH3.

Accepted Answer

N-methyl-3

Question 14

What type of compound results from the reaction of ethyl formate with cyclohexylamine?

Accepted Answer

A)  amide 
B)  1° amine 
C)  acid anhydride 
D)  nitrile 
E)  carboxylate 
A)  amide 
B)  1° amine 
C)  acid anhydride 
D)  nitrile 
E)  carboxylate

Question 15

What is the product of the following reaction?

Accepted Answer

A)  (CH3)3CCH2CH2CH2COOH 
B)  (CH3)3CCH2CH2CH2NH2 
C)  (CH3)3CCH2CH2CH2CH2NH2 
D)  (CH3)3CCH2CH2CH2CONH2 
A)  (CH3)3CCH2CH2CH2COOH 
B)  (CH3)3CCH2CH2CH2NH2 
C)  (CH3)3CCH2CH2CH2CH2NH2 
D)  (CH3)3CCH2CH2CH2CONH2

Question 16

Provide a detailed, stepwise mechanism for the acid-catalyzed transesterification of ethyl acetate with n-propanol.

Accepted Answer

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

Question 17

Give two different one-step methods to convert propanoic acid to methyl propanoate.

Accepted Answer

1) Fischer esterific

Question 18

Arrange the following compounds in order of increasing boiling point: acetic acid, propanenitrile, butane, and acetamide.

Accepted Answer

butane < p

Question 19

Explain while this reaction won't proceed as it is written in the forward direction.

Accepted Answer

Bromide is a weaker

Question 20

Typically, amides will hydrolyze under ________ conditions than esters.

Accepted Answer

A)  stronger 
B)  more dilute 
C)  milder 
D)  less vigorous 
E)  more saline 
A)  stronger 
B)  more dilute 
C)  milder 
D)  less vigorous 
E)  more saline

Exam 21: Carboxylic Acid Derivatives

Provide a detailed, stepwise mechanism for the reaction of with ammonia.

Provide the proper IUPAC name for the compound below.

While the carbonyl stretching frequency for simple aldeydes, ketones, and carboxylic acids is about 1710 cm-1, the carbonyl stretching frequency for esters is about ________.

Provide the name of the compound shown below.

Explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in SN2 reactions.

Which sequence ranks the following carboxylic acid derivatives in order of increasing rate of hydrolysis?

Predict the major organic product in the following reaction.

Which of the following is the most reactive carboxylic acid derivative?

Identify the correct IUPAC systematic name for the structure below.

Amides are less basic than amines because ________.

Provide the proper IUPAC name for NCCH2CH2CH2CH2CO2CH3.

Which of the following reagents convert(s) benzoyl chloride to phenyl propyl ketone?

Provide the proper IUPAC name for ClCH2CH2CONHCH3.

What type of compound results from the reaction of ethyl formate with cyclohexylamine?

What is the product of the following reaction?

Provide a detailed, stepwise mechanism for the acid-catalyzed transesterification of ethyl acetate with n-propanol.

Give two different one-step methods to convert propanoic acid to methyl propanoate.

Arrange the following compounds in order of increasing boiling point: acetic acid, propanenitrile, butane, and acetamide.

Explain while this reaction won't proceed as it is written in the forward direction.

Typically, amides will hydrolyze under ________ conditions than esters.

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

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

While the carbonyl stretching frequency for simple aldeydes, ketones, and carboxylic acids is about 1710 cm^-1, the carbonyl stretching frequency for esters is about ________.

Explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in S_N2 reactions.

Provide the proper IUPAC name for NCCH₂CH₂CH₂CH₂CO₂CH₃.

Provide the proper IUPAC name for ClCH₂CH₂CONHCH₃.