Question 1

Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl.

Accepted Answer

A)   1
B)   2
C)   3
D)   0E) A) and B)
F) A) and C)

Question 2

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

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and B)
F) A) and C)

Question 3

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 IIE) A) and B)
F) B) and D)

Question 4

Predict the product of the following reaction.

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and C)
F) B) and C)

Question 5

Which of the statements about the properties of the carbon-carbon double bond is not true?

Accepted Answer

A)   There is restricted rotation around the carbon-carbon double bond.
B)   Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible.
C)   Trans alkenes are generally more stable than cis alkenes.
D)   The stability of the carbon-carbon double bond increases as the number of substituent groups increases.E) A) and D)
F) B) and D)

Question 6

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4? 2O in the presence of a small amount of H2SO4?   A)  Only I and II B)  Only I and III C)  Only II and III D)  I, II and III" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 7

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.E) B) and D)
F) B) and C)

Question 8

Rearrangements can occur in which of the following reactions?

Accepted Answer

A)   Addition of Cl2 to an alkene.
B)   Addition of HOBr to an alkene.
C)   Addition of H2O/H3O+ to an alkene.
D)   None of the above.E) None of the above
F) A) and B)

Question 9

Which of the following is a terpene?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and B)
F) None of the above

Question 10

Rank the following isomers in order of increasing boiling point, putting the least first.

Accepted Answer

A)   I 
B)   I 
C)   II 
D)   II < I < IIIE) C) and D)
F) B) and C)

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.E) B) and D)
F) B) and C)

Question 12

What is the IUPAC name for the following compound?

Accepted Answer

A)   1-Methylcyclopentene
B)   2-Methyl-1-cyclopentene
C)   1-Methylene-1-methylcyclopentane
D)   1-MethylcyclohexeneE) B) and C)
F) None of the above

Question 13

Which of the following reactions of alkenes takes place with anti stereochemistry only?

Accepted Answer

A)   Addition of HBr
B)   Addition of H2O in the presence of H2SO4
C)   Addition of BH3 followed by H2O2/HO-
D)   Addition of Br2E) A) and D)
F) B) and C) D

Question 14

Which of the following compounds has the highest boiling point?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) A) and C)
F) None of the above

Question 15

Rank the following compounds in order of decreasing stability, putting the most stable first.  II > III B)  II > I > III C)  III > II > I D)  III > I > II" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   I > II > III
B)   II > I > III
C)   III > II > I
D)   III > I > IIE) B) and C)
F) A) and D)

Question 16

What is the major product obtained from the following reaction?

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) B) and D)
F) B) and C) A

Question 17

What is the best choice of reagent to accomplish the following transformation? 2O, Br2 B)  [1] BH3; [2] H2O2/HO- C)  H2O, H2SO4 D)  [1] BH3; [2] H2O" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   H2O, Br2
B)   [1] BH3; [2] H2O2/HO-
C)   H2O, H2SO4
D)   [1] BH3; [2] H2OE) A) and D)
F) A) and C) B

Question 18

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 = ZE) A) and D)
F) All of the above

Question 19

Predict the major product of the following reaction.

Accepted Answer

A)   I
B)   II
C)   III
D)   IVE) All of the above
F) None of the above

Question 20

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

Accepted Answer

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

Exam 10: Alkenes

Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl.

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

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

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Predict the product of the following reaction.

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Which of the statements about the properties of the carbon-carbon double bond is not true?

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

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

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Rearrangements can occur in which of the following reactions?

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Which of the following is a terpene?

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Rank the following isomers in order of increasing boiling point, putting the least first.

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

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What is the IUPAC name for the following compound?

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Which of the following reactions of alkenes takes place with anti stereochemistry only?

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Which of the following compounds has the highest boiling point?

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

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What is the major product obtained from the following reaction?

Correct AnswerverifiedA

What is the best choice of reagent to accomplish the following transformation?

Correct AnswerverifiedB

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

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Predict the major product of the following reaction.

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

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Calculate the degree of unsaturation for a molecule with molecular formula C₆H₁₁Cl.

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

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D

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A

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B

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