Question 1

Show how one might synthesize phenylacetone using toluene, NaCN, and any other necessary reagents.

Accepted Answer

1. Br₂, hν or NBS 2. NaCN 3. CH₃MgBr 4. H₃O⁺

Question 2

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

Accepted Answer

butane < propanenitrile < acetic acid < acetamide

Question 3

Distamycin and derivatives have exhibited antiviral, antibiotic, and antitumor activity by binding to the minor groove of DNA (J. Med. Chem. 2004, 2133). Place a line through each bond of distamycin that would be cleaved by acid hydrolysis.

Accepted Answer

The answer of Distamycin and derivatives have exhibited antiviral, antibiotic,...

Question 4

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 5

Provide the structure of γ-butyrolactam.

Accepted Answer

The answer of Provide the structure of γ-butyrolactam....

Question 6

Provide the proper IUPAC name for ClCH2CH2CONHCH3.

Accepted Answer

N-methyl-3

Question 7

Provide the major organic product in the reaction shown below.

Accepted Answer

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

Question 8

Which of the following statements is/are true?

Accepted Answer

A)  Two equivalents of Grignard reagent react with acid chlorides to yield tertiary alcohols after hydrolysis. 
B)  LiAlH4 reacts with acid chlorides to yield secondary alcohols after hydrolysis. 
C)  LiAlH[OC(CH3)3]3 reacts with acid chlorides to yield primary alcohols after hydrolysis. 
D)  both A and B 
E)  both B and C 
A)  Two equivalents of Grignard reagent react with acid chlorides to yield tertiary alcohols after hydrolysis. 
B)  LiAlH4 reacts with acid chlorides to yield secondary alcohols after hydrolysis. 
C)  LiAlH[OC(CH3)3]3 reacts with acid chlorides to yield primary alcohols after hydrolysis. 
D)  both A and B 
E)  both B and C

Question 9

Provide the proper IUPAC name for the compound below.

Accepted Answer

isopropyl

Question 10

What compound results when benzoic acid reacts with methylamine, and what compound ultimately results when the initially formed compound is heated at 140°C?

Accepted Answer

PhCO₂^- CH₃NH₃⁺

Question 11

Provide the IUPAC name of the following compound.

Accepted Answer

N,N-diethy

Question 12

Propose a synthesis of methyl thioacetate from one carbon compounds and any other necessary inorganic reagents.

Accepted Answer

Beginning with CO₂, 1

Question 13

Describe, in short phrases, the three step mechanism by which hexanoyl chloride reacts with dimethylamine.

Accepted Answer

(i) addition of the nucleophil

Question 14

Provide the proper IUPAC name for NCCH2CH2CH2CH2CO2CH3.

Accepted Answer

methyl 5-c

Question 15

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

Accepted Answer

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

Question 16

Provide an arrow pushing mechanism for the following reaction. Show all
intermediate structures and formal charges. You do not need to show resonance structures.

Accepted Answer

The answer of Provide an arrow pushing mechanism for the...

Question 17

Acids can be converted to primary amines by:

Accepted Answer

A)  conversion to the nitrile followed by treatment with LiAlHS1U1B14S1U1B0. 
B)  conversion to the diazonium salt followed by treatment with NaBHS1U1B14S1U1B0. 
C)  conversion to the primary amide followed by treatment with LiAlHS1U1B14S1U1B0. 
D)  both A and B. 
E)  both A and C. 
A)  conversion to the nitrile followed by treatment with LiAlHS1U1B14S1U1B0. 
B)  conversion to the diazonium salt followed by treatment with NaBHS1U1B14S1U1B0. 
C)  conversion to the primary amide followed by treatment with LiAlHS1U1B14S1U1B0. 
D)  both A and B. 
E)  both A and C.

Question 18

Which of the following are intermediates in the acid hydrolysis of an amide?

Accepted Answer

A)  1 
B)  2 
C)  2 & 3 
D)  4 
E)  1, 2, & 3 
A)  1 
B)  2 
C)  2 & 3 
D)  4 
E)  1, 2, & 3

Question 19

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

Accepted Answer

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

Question 20

Provide the name of the compound shown below.

Accepted Answer

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

Exam 21: Carboxylic Acid Derivatives

Show how one might synthesize phenylacetone using toluene, NaCN, and any other necessary reagents.

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

Distamycin and derivatives have exhibited antiviral, antibiotic, and antitumor activity by binding to the minor groove of DNA (J. Med. Chem. 2004, 2133). Place a line through each bond of distamycin that would be cleaved by acid hydrolysis.

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 structure of γ-butyrolactam.

Provide the proper IUPAC name for ClCH2CH2CONHCH3.

Provide the major organic product in the reaction shown below.

Which of the following statements is/are true?

Provide the proper IUPAC name for the compound below.

What compound results when benzoic acid reacts with methylamine, and what compound ultimately results when the initially formed compound is heated at 140°C?

Provide the IUPAC name of the following compound.

Propose a synthesis of methyl thioacetate from one carbon compounds and any other necessary inorganic reagents.

Describe, in short phrases, the three step mechanism by which hexanoyl chloride reacts with dimethylamine.

Provide the proper IUPAC name for NCCH2CH2CH2CH2CO2CH3.

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

Provide an arrow pushing mechanism for the following reaction. Show all intermediate structures and formal charges. You do not need to show resonance structures.

Acids can be converted to primary amines by:

Which of the following are intermediates in the acid hydrolysis of an amide?

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

Provide the name of the compound shown below.

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

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 ________.

Provide the proper IUPAC name for ClCH₂CH₂CONHCH₃.

Provide the proper IUPAC name for NCCH₂CH₂CH₂CH₂CO₂CH₃.

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