Question 1

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 2

Deduce a reasonable structure for the compound which exhibits the following spectroscopic data.
C5H9ClO2: IR: 2700-3400 cm-1 (broad), 1710 cm-1; 1H NMR (ppm): 1.40 (6H, singlet), 3.60 (2H, singlet), 10.1 (1H, singlet) ppm.

Accepted Answer

(CH₃)₂CClCH₂CO₂H

Question 3

Using acid-base extractions, how might you purify a crude sample of benzoic acid?

Accepted Answer

1) Dissolve sample in ether.
2) Extract with water to remove water-soluble impurities.
3) Extract with sodium bicarbonate to separate benzoate from organic impurities.
4) Acidify aqueous layer and extract benzoic acid into ether.
5) Dry ether layer, filter to remove drying agent, and evaporate ether to give purified benzoic acid.

Question 4

Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation?

Accepted Answer

A)  addition of water 
B)  removal of water as it is formed 
C)  addition of an inorganic acid as a catalyst 
D)  addition of alcohol 
E)  both B and D 
A)  addition of water 
B)  removal of water as it is formed 
C)  addition of an inorganic acid as a catalyst 
D)  addition of alcohol 
E)  both B and D

Question 5

Mark all the sequences of reactions that convert a carboxylic acid to an aldehyde.
(More than one answer is possible.)

Accepted Answer

A)  1) CH2N2 2) DIBAL 3) H3O+ 
B)  1) NaBH4 2) H3O+ 3) PCC 
C)  1) SOCl2 2) LiAl(Ot-Bu)3H 
D)  1) LiAlH4 2) Ag(NH3)2OH 
A)  1) CH2N2 2) DIBAL 3) H3O+ 
B)  1) NaBH4 2) H3O+ 3) PCC 
C)  1) SOCl2 2) LiAl(Ot-Bu)3H 
D)  1) LiAlH4 2) Ag(NH3)2OH

Question 6

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 7

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene and in which Grignard chemistry is employed.

Accepted Answer

1) Br₂, hν

Question 8

What compound is produced when cyclohexene is treated with concentrated KMnO4?

Accepted Answer

A)  hexanoic acid 
B)  adipic acid 
C)  cyclohexanecarboxylic acid 
D)  benzoic acid 
E)  succinic acid 
A)  hexanoic acid 
B)  adipic acid 
C)  cyclohexanecarboxylic acid 
D)  benzoic acid 
E)  succinic acid

Question 9

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 10

2-Phenylethanol yields what acid upon treatment with cold chromic acid?

Accepted Answer

The answer of 2-Phenylethanol yields what acid upon treatment with...

Question 11

Name the compound shown below.

Accepted Answer

3,3,6-trimethyl-6-he

Question 12

What alkyllithium would react with acetic acid to form 2-butanone?

Accepted Answer

A)  methyllithium 
B)  vinyllithium 
C)  ethyllithium 
D)  propyllithium 
E)  phenyllithium 
A)  methyllithium 
B)  vinyllithium 
C)  ethyllithium 
D)  propyllithium 
E)  phenyllithium

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

Provide the structure of 3,3-dimethylheptanoic acid.

Accepted Answer

The answer of Provide the structure of 3,3-dimethylheptanoic acid....

Question 15

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 16

Name the compound shown below.

Accepted Answer

2,4-dimeth

Question 17

LiAl [OC(CH3)3]3H will reduce an acid chloride to an ________.

Accepted Answer

A)  alcohol 
B)  alkane 
C)  acid 
D)  aldehyde 
E)  acetal 
A)  alcohol 
B)  alkane 
C)  acid 
D)  aldehyde 
E)  acetal

Question 18

Provide the major organic product of the following reaction sequence.

Accepted Answer

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

Question 19

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 20

In the mass spectrum of pentanoic acid, the base peak occurs at m/z ________.

Accepted Answer

A)  102 
B)  101 
C)  85 
D)  73 
E)  60 
A)  102 
B)  101 
C)  85 
D)  73 
E)  60

Exam 20: Carboxylic Acids

Provide the major organic product of the following reaction sequence.

Deduce a reasonable structure for the compound which exhibits the following spectroscopic data. C5H9ClO2: IR: 2700-3400 cm-1 (broad), 1710 cm-1; 1H NMR (ppm): 1.40 (6H, singlet), 3.60 (2H, singlet), 10.1 (1H, singlet) ppm.

Using acid-base extractions, how might you purify a crude sample of benzoic acid?

Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation?

Mark all the sequences of reactions that convert a carboxylic acid to an aldehyde. (More than one answer is possible.)

Provide the major organic product of the following reaction sequence.

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene and in which Grignard chemistry is employed.

What compound is produced when cyclohexene is treated with concentrated KMnO4?

Provide the major organic product of the reaction shown below.

2-Phenylethanol yields what acid upon treatment with cold chromic acid?

Name the compound shown below.

What alkyllithium would react with acetic acid to form 2-butanone?

Provide the major organic product of the following reaction.

Provide the structure of 3,3-dimethylheptanoic acid.

Provide the major organic product of the following reaction sequence.

Name the compound shown below.

LiAl [OC(CH3)3]3H will reduce an acid chloride to an ________.

Provide the major organic product of the following reaction sequence.

Provide the major organic product of the reaction shown below.

In the mass spectrum of pentanoic acid, the base peak occurs at m/z ________.

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 Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Deduce a reasonable structure for the compound which exhibits the following spectroscopic data. C₅H₉ClO₂: IR: 2700-3400 cm^-1 (broad), 1710 cm^-1; ¹H NMR (ppm): 1.40 (6H, singlet), 3.60 (2H, singlet), 10.1 (1H, singlet) ppm.

What compound is produced when cyclohexene is treated with concentrated KMnO₄?

LiAl [OC(CH₃)₃]₃H will reduce an acid chloride to an ________.