Question 1

What are secondary alcohols oxidized to?

Accepted Answer

A)  tertiary alcohols 
B)  ethers 
C)  esters 
D)  aldehydes 
E)  ketones 
A)  tertiary alcohols 
B)  ethers 
C)  esters 
D)  aldehydes 
E)  ketones

Question 2

Arrange the following in order from least oxidized to most oxidized.

Accepted Answer

A)  II < I < III 
B)  III < I = II 
C)  III < I < II 
D)  I < II < III 
E)  I < III < II 
A)  II < I < III 
B)  III < I = II 
C)  III < I < II 
D)  I < II < III 
E)  I < III < II

Question 3

Arrange the following in order from most oxidized to least oxidized.

Accepted Answer

A)  II > I > III 
B)  III > II > I 
C)  III > I > II 
D)  I > II > III 
E)  II > III > I 
A)  II > I > III 
B)  III > II > I 
C)  III > I > II 
D)  I > II > III 
E)  II > III > I

Question 4

Match the following.
-reducing agent

Accepted Answer

A) substitution at saturated carbon atom, mechanism 
B) methoxide 
C) LiAlH4 
D) elimination reaction mechanism 
E) CN-
F)hemiketal
G)H+
H)Jones reagent
I)step-growth 
A) substitution at saturated carbon atom, mechanism 
B) methoxide 
C) LiAlH4 
D) elimination reaction mechanism 
E) CN-
F)hemiketal
G)H+
H)Jones reagent
I)step-growth

Question 5

What are the correct products of the following reaction performed in the presence of an acid? C3H7COOH + C2H5OH →

Accepted Answer

A)  C3H7COC2H5 + H2O + 1/2O2 
B)  C3H7C(=O)OC2H5 + H2O 
C)  C3H7C(OH)OC2H5 + H3O+ 
D)  CH3CH2C(=O)OC3H7 + H2O 
E)  C3H7C(=O)-O-O-C2H5 + H2O 
A)  C3H7COC2H5 + H2O + 1/2O2 
B)  C3H7C(=O)OC2H5 + H2O 
C)  C3H7C(OH)OC2H5 + H3O+ 
D)  CH3CH2C(=O)OC3H7 + H2O 
E)  C3H7C(=O)-O-O-C2H5 + H2O

Question 6

Find the suitable base for the following reaction: C6H5OH + :B → C6H5O:- + H:B+
The pKa for C6H5OH (phenol) is 9.88. The formula for the base is followed by the pKa of its conjugate acid.

Accepted Answer

A)  CN-, pKa = 9.31 
B)  CF3COO-, pKa = 0.23 
C)  CH3C(=O)CH3, pKa = -7.2 
D)  CH3COO-, pKa = 4.74 
E)  OH-, pKa = 15.73 
A)  CN-, pKa = 9.31 
B)  CF3COO-, pKa = 0.23 
C)  CH3C(=O)CH3, pKa = -7.2 
D)  CH3COO-, pKa = 4.74 
E)  OH-, pKa = 15.73

Question 7

Identify the organic product for the following reaction. 
CH3CH2COOH + CH3CH2CH2NH2

Accepted Answer

A)  CH3CH2NHCH2CH2CH3 
B)  CH3CH2CON(CH2CH2CH3)2 
C)  CH3CH2CH2CONHCH2CH3 
D)  CH3CH2CONHCH2CH2CH3 
E)  CH3CH2N(CH2CH2CH3)2 
A)  CH3CH2NHCH2CH2CH3 
B)  CH3CH2CON(CH2CH2CH3)2 
C)  CH3CH2CH2CONHCH2CH3 
D)  CH3CH2CONHCH2CH2CH3 
E)  CH3CH2N(CH2CH2CH3)2

Question 8

Which of the following is the balanced chemical equation for the addition of HBr to CH2=CHCH2CH3?

Accepted Answer

A)  CH2=CHCH2CH3 + HBr → CH2BrCH2CH2CH3 
B)  CH2=CHCH2CH3 + 2HBr → 2CH2BrCH3 
C)  CH2=CHCH2CH3 + 2HBr → CH3Br + CH2BrCH2CH3 
D)  CH2=CHCH2CH3 + 4HBr → 4CH3Br 
E)  CH2=CHCH2CH3 + HBr → CH3CHBrCH2CH3 
A)  CH2=CHCH2CH3 + HBr → CH2BrCH2CH2CH3 
B)  CH2=CHCH2CH3 + 2HBr → 2CH2BrCH3 
C)  CH2=CHCH2CH3 + 2HBr → CH3Br + CH2BrCH2CH3 
D)  CH2=CHCH2CH3 + 4HBr → 4CH3Br 
E)  CH2=CHCH2CH3 + HBr → CH3CHBrCH2CH3

Question 9

Identify the major product in the following reaction:

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 10

Match the following.
-E2

Accepted Answer

A) substitution at saturated carbon atom, mechanism 
B) methoxide 
C) LiAlH4 
D) elimination reaction mechanism 
E) CN-
F)hemiketal
G)H+
H)Jones reagent
I)step-growth 
A) substitution at saturated carbon atom, mechanism 
B) methoxide 
C) LiAlH4 
D) elimination reaction mechanism 
E) CN-
F)hemiketal
G)H+
H)Jones reagent
I)step-growth

Question 11

What is the correct order of increasing reactivity among acyl groups?

Accepted Answer

A)  acyl chloride < acid anhydride < carboxylic acid < amide 
B)  acyl chloride < carboxylic acid < acid anhydride < amide 
C)  acyl chloride < amide < carboxylic acid < acid anhydride 
D)  amide < carboxylic acid < acid anhydride < acyl chloride 
E)  amide < acyl chloride < acid anhydride < carboxylic acid 
A)  acyl chloride < acid anhydride < carboxylic acid < amide 
B)  acyl chloride < carboxylic acid < acid anhydride < amide 
C)  acyl chloride < amide < carboxylic acid < acid anhydride 
D)  amide < carboxylic acid < acid anhydride < acyl chloride 
E)  amide < acyl chloride < acid anhydride < carboxylic acid

Question 12

What is a hemiacetal?

Accepted Answer

A)  A hemiacetal, prepared from an alcohol and an aldehyde, is a compound that contains both OH and OR groups on the same carbon. 
B)  Compounds prepared from ketones and alcohols and with OH and OR groups on the same carbon are known as hemiacetals. 
C)  A hemiacetal is a product of acetyl group hydrolysis; it contains a COOH group. 
D)  A hemiacetal is formed from alcohols and acetic acid; a hemiacetal has both acetyl and OH groups on the same carbon atom. 
E)  A hemiacetal, formed from an aldehyde and an alcohol, has OH and aldehyde groups on adjacent carbon atoms in its structure. 
A)  A hemiacetal, prepared from an alcohol and an aldehyde, is a compound that contains both OH and OR groups on the same carbon. 
B)  Compounds prepared from ketones and alcohols and with OH and OR groups on the same carbon are known as hemiacetals. 
C)  A hemiacetal is a product of acetyl group hydrolysis; it contains a COOH group. 
D)  A hemiacetal is formed from alcohols and acetic acid; a hemiacetal has both acetyl and OH groups on the same carbon atom. 
E)  A hemiacetal, formed from an aldehyde and an alcohol, has OH and aldehyde groups on adjacent carbon atoms in its structure.

Question 13

Match the following.
-formed from a ketone and alcohol

Accepted Answer

A) substitution at saturated carbon atom, mechanism 
B) methoxide 
C) LiAlH4 
D) elimination reaction mechanism 
E) CN-
F)hemiketal
G)H+
H)Jones reagent
I)step-growth 
A) substitution at saturated carbon atom, mechanism 
B) methoxide 
C) LiAlH4 
D) elimination reaction mechanism 
E) CN-
F)hemiketal
G)H+
H)Jones reagent
I)step-growth

Question 14

Give the organic product for the following reaction. CH3CH2CH2NH2 + HCl

Accepted Answer

A)  ClCH2CH2CH2NH2 
B)  CH3CHClCH2NH2 
C)  CH3CH2CHClNH2 
D)  CH3CH2CH2NHCl 
E)  CH3CH2CH2NH3+Cl- 
A)  ClCH2CH2CH2NH2 
B)  CH3CHClCH2NH2 
C)  CH3CH2CHClNH2 
D)  CH3CH2CH2NHCl 
E)  CH3CH2CH2NH3+Cl-

Question 15

Why doesn't benzene typically undergo addition reactions like the alkenes do?

Accepted Answer

Benzene's pi electrons are del

Question 16

Which of the following five substrates is the most likely to be the substrate in an SN2 reaction?

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 of the following is a balanced chemical equation that represents the reaction of 3-ethyl-2-methylhexene with HBr?

Accepted Answer

A)  C9H18 + HBr → C9H20 + Br2 
B)  C9H20 + HBr → C9H20 + Br2 
C)  C9H18 + 2HBr → C9H18Br2 + H2 
D)  C9H18 + HBr → C9H19Br 
E)  C6H12 + HBr → C6H11Br + HBr 
A)  C9H18 + HBr → C9H20 + Br2 
B)  C9H20 + HBr → C9H20 + Br2 
C)  C9H18 + 2HBr → C9H18Br2 + H2 
D)  C9H18 + HBr → C9H19Br 
E)  C6H12 + HBr → C6H11Br + HBr

Question 18

Draw a clear mechanism for E2 elimination reactions. Make sure to indicate each step of the mechanism (if there is more than one) as well as to use arrows to show the electron flow.

Accepted Answer

E2 elimination reactions involve the rem

Question 19

Complete and balance the following complete hydrogenation reaction: CH3CH2C   CCH3 + 2H2 → ?

Accepted Answer

A)  CH3CH2C   CCH3 + 3H2 → CH3CH2CH3 + CH3CH3 
B)  CH3CH2C   CCH3 + 2H2 → CH3CH2CH2CH2CH3 
C)  CH3CH2C   CCH3 + 6H2 → 5CH4 
D)  2CH3CH2C   CCH3 + 2H2 → CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 
E)  CH3CH2C   CCH3 + 2H2 → CH3CH2CH2     CH2CH3 
A)  CH3CH2C   CCH3 + 3H2 → CH3CH2CH3 + CH3CH3 
B)  CH3CH2C   CCH3 + 2H2 → CH3CH2CH2CH2CH3 
C)  CH3CH2C   CCH3 + 6H2 → 5CH4 
D)  2CH3CH2C   CCH3 + 2H2 → CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 
E)  CH3CH2C   CCH3 + 2H2 → CH3CH2CH2     CH2CH3

Question 20

What is the product obtained from the reaction between a ketone and a primary alcohol?

Accepted Answer

A)  a secondary alcohol 
B)  a tertiary alcohol 
C)  a hemiacetal 
D)  a hemiketal 
E)  a carboxylic acid 
A)  a secondary alcohol 
B)  a tertiary alcohol 
C)  a hemiacetal 
D)  a hemiketal 
E)  a carboxylic acid

Exam 21: Organic Chemistry Ii: Reactions

What are secondary alcohols oxidized to?

Arrange the following in order from least oxidized to most oxidized.

Arrange the following in order from most oxidized to least oxidized.

Match the following. -reducing agent

What are the correct products of the following reaction performed in the presence of an acid? C3H7COOH + C2H5OH →

Find the suitable base for the following reaction: C6H5OH + :B → C6H5O:- + H:B+ The pKa for C6H5OH (phenol) is 9.88. The formula for the base is followed by the pKa of its conjugate acid.

Identify the organic product for the following reaction. CH3CH2COOH + CH3CH2CH2NH2

Which of the following is the balanced chemical equation for the addition of HBr to CH2=CHCH2CH3?

Identify the major product in the following reaction:

Match the following. -E2

What is the correct order of increasing reactivity among acyl groups?

What is a hemiacetal?

Match the following. -formed from a ketone and alcohol

Give the organic product for the following reaction. CH3CH2CH2NH2 + HCl

Why doesn't benzene typically undergo addition reactions like the alkenes do?

Which of the following five substrates is the most likely to be the substrate in an SN2 reaction?

Which of the following is a balanced chemical equation that represents the reaction of 3-ethyl-2-methylhexene with HBr?

Draw a clear mechanism for E2 elimination reactions. Make sure to indicate each step of the mechanism (if there is more than one) as well as to use arrows to show the electron flow.

Complete and balance the following complete hydrogenation reaction: CH3CH2C CCH3 + 2H2 → ?

What is the product obtained from the reaction between a ketone and a primary alcohol?

Units of Measurement for Physical and Chemical Change

Atoms and Elements

Molecules, Compounds, and Nomenclature

Chemical Reactions and Stoichiometry

Gases

Thermochemistry

The Quantum-Mechanical Model of the Atom

Periodic Properties of the Elements

Chemical Bonding I: Lewis Theory

Chemical Bonding Ii: Molecular Shapes, Valence Bond Theory, and Molecular Orbital Theory

Liquids, Solids, and Intermolecular Forces

Solutions

Chemical Kinetics

Chemical Equilibrium

Acids and Bases

Aqueous Ionic Equilibrium

Gibbs Energy and Thermodynamics

Electrochemistry

Radioactivity and Nuclear Chemistry

Organic Chemistry I: Structures

Biochemistry

Chemistry of the Nonmetals

Metals and Metallurgy

Transition Metals and Coordination Compounds

Filters

What are the correct products of the following reaction performed in the presence of an acid? C₃H₇COOH + C₂H₅OH →

Find the suitable base for the following reaction: C₆H₅OH + :B → C₆H₅O:^- + H:B⁺ The pK_a for C₆H₅OH (phenol) is 9.88. The formula for the base is followed by the pK_a of its conjugate acid.

Identify the organic product for the following reaction. CH₃CH₂COOH + CH₃CH₂CH₂NH₂

Which of the following is the balanced chemical equation for the addition of HBr to CH₂=CHCH₂CH₃?

Give the organic product for the following reaction. CH₃CH₂CH₂NH₂ + HCl

Which of the following five substrates is the most likely to be the substrate in an S_N² reaction?

Complete and balance the following complete hydrogenation reaction: CH₃CH₂C CCH₃ + 2H₂ → ?