Question 1

Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true?

Accepted Answer

A) Achiral starting materials yield an unequal mixture of two enantiomers. 
B) Hydrohalogenation occurs with syn stereochemistry only. 
C) Hydrohalogenation occurs with anti stereochemistry only. 
D) Hydrohalogenation occurs with syn and anti addition of HX. 
A) Achiral starting materials yield an unequal mixture of two enantiomers. 
B) Hydrohalogenation occurs with syn stereochemistry only. 
C) Hydrohalogenation occurs with anti stereochemistry only. 
D) Hydrohalogenation occurs with syn and anti addition of HX.

Question 2

What is the common name of the following compound?

Accepted Answer

A) 2-Vinylcyclohexene 
B) 2-Allylcyclohexene 
C) 1-Allylcyclohexene 
D) 1-Vinylcyclohexene 
A) 2-Vinylcyclohexene 
B) 2-Allylcyclohexene 
C) 1-Allylcyclohexene 
D) 1-Vinylcyclohexene

Question 3

What is the IUPAC name for the following compound?

Accepted Answer

A) 1,2-Dimethylcyclohexene 
B) 2,3-Dimethylcyclohexene 
C) 1,6-Dimethylcyclohexene 
D) 1,2-Dimethyl-3-cyclohexene 
A) 1,2-Dimethylcyclohexene 
B) 2,3-Dimethylcyclohexene 
C) 1,6-Dimethylcyclohexene 
D) 1,2-Dimethyl-3-cyclohexene

Question 4

Which of the following statements about alkenes is true?

Accepted Answer

A) Alkenes react with nucleophiles and bases. 
B) Alkenes contain double bonds from two sp-hybridized carbon atoms. 
C) In the reactions of alkenes,the   bond is not always broken. 
D) Alkenes react with electrophiles. 
A) Alkenes react with nucleophiles and bases. 
B) Alkenes contain double bonds from two sp-hybridized carbon atoms. 
C) In the reactions of alkenes,the   bond is not always broken. 
D) Alkenes react with electrophiles.

Question 5

Which of the following alkenes is an E alkene?

Accepted Answer

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

Question 6

What is (are)the major product(s)obtained from the following reaction?

Accepted Answer

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

Question 7

What is the major product of the following reaction?

Accepted Answer

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

Question 8

Predict the product of the following reaction,ignoring stereochemistry.

Accepted Answer

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

Question 9

What is the IUPAC name of the following compound?

Accepted Answer

A) (E,R)-4-bromo-4-hexen-2-ol 
B) (Z,R)-4-bromo-4-hexen-2-ol 
C) (E,S)-4-bromo-4-hexen-2-ol 
D) (Z,S)-4-bromo-4-hexen-2-ol 
A) (E,R)-4-bromo-4-hexen-2-ol 
B) (Z,R)-4-bromo-4-hexen-2-ol 
C) (E,S)-4-bromo-4-hexen-2-ol 
D) (Z,S)-4-bromo-4-hexen-2-ol

Question 10

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?

Accepted Answer

A) Only I and II 
B) Only I and III 
C) Only II and III 
D) I,II,and III 
A) Only I and II 
B) Only I and III 
C) Only II and III 
D) I,II,and III

Question 11

Which of the following statements about hydroboration/oxidation of alkenes is true?

Accepted Answer

A) In hydroboration,the boron atom bonds to the more substituted carbon. 
B) Hydroboration occurs with anti addition. 
C) Oxidation occurs with retention of configuration. 
D) 9-BBN does not undergo hydroboration in the same manner as BH3. 
A) In hydroboration,the boron atom bonds to the more substituted carbon. 
B) Hydroboration occurs with anti addition. 
C) Oxidation occurs with retention of configuration. 
D) 9-BBN does not undergo hydroboration in the same manner as BH3.

Question 12

In which of the following alkene addition reactions will carbocation rearrangements occur?

Accepted Answer

A) Addition of Br2 and H2O 
B) Addition of Br2 
C) Addition of Cl2 and H2O 
D) Addition of H2O in the presence of H2SO4 
A) Addition of Br2 and H2O 
B) Addition of Br2 
C) Addition of Cl2 and H2O 
D) Addition of H2O in the presence of H2SO4

Question 13

Rank the following compounds in order of decreasing stability,putting the most stable first.

Accepted Answer

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

Question 14

What is the major product obtained from the following reaction (assume enantiomer is also formed)?

Accepted Answer

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

Question 15

Markovnikov addition of HBr to CH3CH=CH2 involves which of the following?

Accepted Answer

A) Initial attack by bromide anion (Br-). 
B) Initial attack by bromine radical (Br•). 
C) Formation of a primary carbocation. 
D) Formation of a secondary carbocation. 
A) Initial attack by bromide anion (Br-). 
B) Initial attack by bromine radical (Br•). 
C) Formation of a primary carbocation. 
D) Formation of a secondary carbocation.

Question 16

What is (are)the missing reagent(s)in the following reaction?

Accepted Answer

A) Br2/CCl4 
B) NBS,DMSO/H2O 
C) [1] Br2; [2] H2O 
D) [1] BH3; [2] H2O2/HO- 
A) Br2/CCl4 
B) NBS,DMSO/H2O 
C) [1] Br2; [2] H2O 
D) [1] BH3; [2] H2O2/HO-

Question 17

Rank the carbocation in order of increasing stability,putting the least stable first.

Accepted Answer

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

Question 18

Predict the major product(s)of the following reaction.

Accepted Answer

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

Question 19

Predict the product(s)of the following reaction.

Accepted Answer

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

Question 20

Label each C-C double bond in Kavain,a naturally occurring relaxant,as E or Z.

Accepted Answer

A) I = Z and II = Z 
B) I = Z and II = E 
C) I = E and II = E 
D) I = E and II = Z 
A) I = Z and II = Z 
B) I = Z and II = E 
C) I = E and II = E 
D) I = E and II = Z

Exam 10: Alkenes and Addition Reactions

Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true?

What is the common name of the following compound?

What is the IUPAC name for the following compound?

Which of the following statements about alkenes is true?

Which of the following alkenes is an E alkene?

What is (are)the major product(s)obtained from the following reaction?

What is the major product of the following reaction?

Predict the product of the following reaction,ignoring stereochemistry.

What is the IUPAC name of the following compound?

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?

Which of the following statements about hydroboration/oxidation of alkenes is true?

In which of the following alkene addition reactions will carbocation rearrangements occur?

Rank the following compounds in order of decreasing stability,putting the most stable first.

What is the major product obtained from the following reaction (assume enantiomer is also formed)?

Markovnikov addition of HBr to CH3CH=CH2 involves which of the following?

What is (are)the missing reagent(s)in the following reaction?

Rank the carbocation in order of increasing stability,putting the least stable first.

Predict the major product(s)of the following reaction.

Predict the product(s)of the following reaction.

Label each C-C double bond in Kavain,a naturally occurring relaxant,as E or Z.

Structure and Bonding

Acids and Bases

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

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H₂O in the presence of a small amount of H₂SO₄?

Markovnikov addition of HBr to CH₃CH=CH₂ involves which of the following?