Question 1

Which of the following would be the strongest acid?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 2

Which compound would be expected to have the highest pKa?

Accepted Answer

A) water 
B) acetic acid 
C) ethane 
D) acetylene 
E) ethanol 
A) water 
B) acetic acid 
C) ethane 
D) acetylene 
E) ethanol

Question 3

A compound has the molecular formula C8H14O4.Its IR spectrum shows a strong absorption band near 1740 cm-1.Its 1H NMR spectrum consists of: triplet,$\delta$1.3
Singlet,$\delta$ 2.6
Quartet,$\delta$ 4.2
The most likely structure for the compound is:

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 4

What would be the final product,F,of the following sequence of reactions?

Accepted Answer

A) 1-Bromo-2-methyl propane 
B) 3-Bromo-3-methylbutanoic acid 
C) Butanoic acid 
D) 3-Methylbutanoic acid 
E) Methyl 2-methylproanoate 
A) 1-Bromo-2-methyl propane 
B) 3-Bromo-3-methylbutanoic acid 
C) Butanoic acid 
D) 3-Methylbutanoic acid 
E) Methyl 2-methylproanoate

Question 5

Given a mixture of benzyl alcohol,phenol,and benzoic acid dissolved in ether,outline in a flow diagram an extraction method to separate each.

Accepted Answer

The answer of Given a mixture of benzyl alcohol,phenol,and benzoic...

Question 6

An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol)is called a ___.

Accepted Answer

Fischer es

Question 7

Which of the following is the best name for the following compound?

Accepted Answer

A) Isobutyl ethanoate 
B) Ethyl isopropanoate 
C) 3-methylbutyl ethanoate 
D) Ethoxy isobutyl ketone 
E) Ethyl 3-methylbutanoate 
A) Isobutyl ethanoate 
B) Ethyl isopropanoate 
C) 3-methylbutyl ethanoate 
D) Ethoxy isobutyl ketone 
E) Ethyl 3-methylbutanoate

Question 8

Which of the following acids would be expected to have the smallest value for pKa?

Accepted Answer

A) Benzoic acid 
B) 4-Nitrobenzoic acid 
C) 4-Methylbenzoic acid 
D) 4-Methoxybenzoic acid 
E) 4-Iodobenzoic acid 
A) Benzoic acid 
B) 4-Nitrobenzoic acid 
C) 4-Methylbenzoic acid 
D) 4-Methoxybenzoic acid 
E) 4-Iodobenzoic acid

Question 9

The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm-1 and a sharp band at 1710 cm-1.Which of these compounds could it be?

Accepted Answer

A) 1-Butanol 
B) Propyl acetate 
C) Butanoic acid 
D) Acetyl chloride 
E) Acetic anhydride 
A) 1-Butanol 
B) Propyl acetate 
C) Butanoic acid 
D) Acetyl chloride 
E) Acetic anhydride

Question 10

Suggest a structure consistent with the following spectroscopic data:
C5H10O2
IR: 1745 cm−1
1H NMR: 
   13C NMR
Broadband decoupled: 10.41,20.91,22.14,66.10,171.09 $\delta$
DEPT 90: no peaks
DEPT 135: 10.41,20.91 $\delta$ (positive); 22.14,66.10 $\delta$ (negative)

Accepted Answer

The answer of Suggest a structure consistent with the following...

Question 11

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

Accepted Answer

A) CH3CHO 
B) CH3COCl 
C) (CH3CO)2O 
D) CH3CONH2 
E) CH3CO2CH3 
A) CH3CHO 
B) CH3COCl 
C) (CH3CO)2O 
D) CH3CONH2 
E) CH3CO2CH3

Question 12

Complete the following reaction sequence,giving details of all significant intermediates.

Accepted Answer

The answer of Complete the following reaction sequence,giving details of...

Question 13

Which of the following would be the strongest acid?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 14

What is the product of this reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 15

What is the expected product,A,of the following reaction sequence?

Accepted Answer

A) HCO2CH2C6H5 
B) C6H5CH2COOH 
C) C6H5CH2OSO3H 
D) C6H5CHClCOOH 
E) O=C(CH2C6H5)2 
A) HCO2CH2C6H5 
B) C6H5CH2COOH 
C) C6H5CH2OSO3H 
D) C6H5CHClCOOH 
E) O=C(CH2C6H5)2

Question 16

Which of the following structures is 3,4-dimethylpentyl chloroformate?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 17

Which compound would be the weakest acid?

Accepted Answer

A) CHCl2CH2CH2CO2H 
B) ClCH2CHClCH2CO2H 
C) CH3CCl2CH2CO2H 
D) CH3CHClCHClCO2H 
E) CH3CH2CCl2CO2H 
A) CHCl2CH2CH2CO2H 
B) ClCH2CHClCH2CO2H 
C) CH3CCl2CH2CO2H 
D) CH3CHClCHClCO2H 
E) CH3CH2CCl2CO2H

Question 18

Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?

Accepted Answer

A)    
B)    
C)    
D) All of these choices. 
E) Only two of these choices. 
A)    
B)    
C)    
D) All of these choices. 
E) Only two of these choices.

Question 19

Draw the structure for 3-ethyl-4,4-dimethylhexanenitrile.

Accepted Answer

The answer of Draw the structure for 3-ethyl-4,4-dimethylhexanenitrile....

Question 20

Which of the following would be the weakest acid?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Exam 17: Carboxylic Acids and Their Derivatives

Which of the following would be the strongest acid?

Which compound would be expected to have the highest pKa?

A compound has the molecular formula C8H14O4.Its IR spectrum shows a strong absorption band near 1740 cm-1.Its 1H NMR spectrum consists of: triplet, δ\deltaδ 1.3 Singlet, δ\deltaδ 2.6 Quartet, δ\deltaδ 4.2 The most likely structure for the compound is:

What would be the final product,F,of the following sequence of reactions?

Given a mixture of benzyl alcohol,phenol,and benzoic acid dissolved in ether,outline in a flow diagram an extraction method to separate each.

An acid-catalyzed esterification (a reaction between a carboxylic acid and an alcohol)is called a ___.

Which of the following is the best name for the following compound?

Which of the following acids would be expected to have the smallest value for pKa?

The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm-1 and a sharp band at 1710 cm-1.Which of these compounds could it be?

Suggest a structure consistent with the following spectroscopic data: C5H10O2 IR: 1745 cm−1 1H NMR: 13C NMR Broadband decoupled: 10.41,20.91,22.14,66.10,171.09 δ\deltaδ DEPT 90: no peaks DEPT 135: 10.41,20.91 δ\deltaδ (positive); 22.14,66.10 δ\deltaδ (negative)

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

Complete the following reaction sequence,giving details of all significant intermediates.

Which of the following would be the strongest acid?

What is the product of this reaction?

What is the expected product,A,of the following reaction sequence?

Which of the following structures is 3,4-dimethylpentyl chloroformate?

Which compound would be the weakest acid?

Which of the following would serve as a synthesis of 2,2-dimethylpropanoic acid?

Draw the structure for 3-ethyl-4,4-dimethylhexanenitrile.

Which of the following would be the weakest acid?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which compound would be expected to have the highest pK_a?

Which of the following acids would be expected to have the smallest value for pK_a?

The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm^-1 and a sharp band at 1710 cm^-1.Which of these compounds could it be?