Question 1

Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH)and ethanol (CH3CH2OH)?

Accepted Answer

A) Hybridization 
B) Electronegativity 
C) Resonance 
D) Size 
A) Hybridization 
B) Electronegativity 
C) Resonance 
D) Size

Question 2

What is the correct classification of the following compound? CH3-O-CH3

Accepted Answer

A) Brønsted-Lowry acid and Lewis acid 
B) Brønsted-Lowry base and Lewis base 
C) Brønsted-Lowry base 
D) Lewis base 
A) Brønsted-Lowry acid and Lewis acid 
B) Brønsted-Lowry base and Lewis base 
C) Brønsted-Lowry base 
D) Lewis base

Question 3

Which of the following would have the lowest pKa?

Accepted Answer

A) ClCH2CH2CH2CH2COOH 
B) CH3CHClCH2CH2COOH 
C) CH3CH2CHClCH2COOH 
D) CH3CH2CH2CHClCOOH 
A) ClCH2CH2CH2CH2COOH 
B) CH3CHClCH2CH2COOH 
C) CH3CH2CHClCH2COOH 
D) CH3CH2CH2CHClCOOH

Question 4

Identify the acid/conjugate acid (in that order)in the following reaction:

Accepted Answer

A) I,III 
B) I,IV 
C) II,III 
D) II,IV 
A) I,III 
B) I,IV 
C) II,III 
D) II,IV

Question 5

Which of the following species is the strongest base?

Accepted Answer

A) HO- 
B) H2N- 
C) CH3COO- 
D) Cl- 
A) HO- 
B) H2N- 
C) CH3COO- 
D) Cl-

Question 6

Which of the following species is the conjugate acid of ammonia,NH3?

Accepted Answer

A) H4N 
B) H3N+ 
C) H2N- 
D) H4N+ 
A) H4N 
B) H3N+ 
C) H2N- 
D) H4N+

Question 7

Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2)and ethylene (C2H4)?

Accepted Answer

A) Size 
B) Resonance 
C) Inductive effect 
D) Hybridization 
A) Size 
B) Resonance 
C) Inductive effect 
D) Hybridization

Question 8

Consider the following structures I-IV.Which two species represent constitutional isomers?

Accepted Answer

A) I and II 
B) I and III 
C) I and IV 
D) II and IV 
A) I and II 
B) I and III 
C) I and IV 
D) II and IV

Question 9

Which of the following will proceed as written?

Accepted Answer

A) CH3ONa + HCl → CH3OH + NaCl 
B) CH3OH + NaCl → NaOEt + HCl 
C) CH3OH + H2O → CH3O- + H3O+ 
D) CH3OH + NH3 → CH3O- + NH4± 
A) CH3ONa + HCl → CH3OH + NaCl 
B) CH3OH + NaCl → NaOEt + HCl 
C) CH3OH + H2O → CH3O- + H3O+ 
D) CH3OH + NH3 → CH3O- + NH4±

Question 10

What is the direction of equilibrium when acetylene (C2H2)reacts with ethoxide (CH3CH2O-)in an acid-base reaction?

Accepted Answer

A) Left 
B) Right 
C) Neither 
D) Cannot be determined 
A) Left 
B) Right 
C) Neither 
D) Cannot be determined

Question 11

Which of the following is the strongest base?

Accepted Answer

A) CH3COCH3 
B) CH3COOH 
C) NH3 
D) H2O 
A) CH3COCH3 
B) CH3COOH 
C) NH3 
D) H2O

Question 12

Identify the Lewis acid in the following reaction.

Accepted Answer

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

Question 13

Rank the following compounds in order of decreasing acidity,putting the most acidic first.

Accepted Answer

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

Question 14

Consider the following molecule with protons labeled,I-III.Rank these protons in order of decreasing acidity,putting the most acidic first.

Accepted Answer

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

Question 15

Rank the following compounds in order of decreasing acidity,putting the most acidic first.

Accepted Answer

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

Question 16

Consider the following structures I-IV.Which two species represent resonance structures?

Accepted Answer

A) I and II 
B) I and III 
C) I and IV 
D) II and IV 
A) I and II 
B) I and III 
C) I and IV 
D) II and IV

Question 17

Rank the following compounds in order of decreasing acidity,putting the most acidic first.

Accepted Answer

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

Question 18

Identify the base/conjugate base (in that order)in the following reaction:

Accepted Answer

A) I,III 
B) I,IV 
C) II,III 
D) II,IV 
A) I,III 
B) I,IV 
C) II,III 
D) II,IV

Question 19

Which of the following ranks the compounds in order of increasing basicity,putting the least basic first?

Accepted Answer

A) CH3NH2 3OH 4 
B) CH3OH 3NH2 4 
C) CH4 3NH2 3OH 
D) CH4 3OH 3NH2 
A) CH3NH2 3OH 4 
B) CH3OH 3NH2 4 
C) CH4 3NH2 3OH 
D) CH4 3OH 3NH2

Exam 2: Acids and Bases

Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH)and ethanol (CH3CH2OH)?

What is the correct classification of the following compound? CH3-O-CH3

Which of the following would have the lowest pKa?

Identify the acid/conjugate acid (in that order)in the following reaction:

Which of the following species is the strongest base?

Which of the following species is the conjugate acid of ammonia,NH3?

Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2)and ethylene (C2H4)?

Consider the following structures I-IV.Which two species represent constitutional isomers?

Which of the following will proceed as written?

What is the direction of equilibrium when acetylene (C2H2)reacts with ethoxide (CH3CH2O-)in an acid-base reaction?

Which of the following is the strongest base?

Identify the Lewis acid in the following reaction.

Rank the following compounds in order of decreasing acidity,putting the most acidic first.

Consider the following molecule with protons labeled,I-III.Rank these protons in order of decreasing acidity,putting the most acidic first.

Rank the following compounds in order of decreasing acidity,putting the most acidic first.

Consider the following structures I-IV.Which two species represent resonance structures?

Rank the following compounds in order of decreasing acidity,putting the most acidic first.

Identify the base/conjugate base (in that order)in the following reaction:

Which of the following ranks the compounds in order of increasing basicity,putting the least basic first?

Structure and Bonding

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH₃COOH)and ethanol (CH₃CH₂OH)?

What is the correct classification of the following compound? CH₃-O-CH₃

Which of the following species is the conjugate acid of ammonia,NH₃?

Which of the following concepts can be used to explain the difference in acidity between acetylene (C₂H₂)and ethylene (C₂H₄)?

What is the direction of equilibrium when acetylene (C₂H₂)reacts with ethoxide (CH₃CH₂O^-)in an acid-base reaction?