Question 1

Which of the following compounds will not produce methylcyclopentane after catalytic hydrogenation?

Accepted Answer

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

Question 2

A student wanted to use the branched groups, isobutyl, sec-butyl, and tert-butyl when naming alkenes, but was told not to. What is the correct IUPAC name for the compound the student called sec-butylethene?

Accepted Answer

A)  4-methyl-1-pentene 
B)  3-methyl-1-pentene 
C)  3,3-dimethyl-1-butene 
D)  none of these 
A)  4-methyl-1-pentene 
B)  3-methyl-1-pentene 
C)  3,3-dimethyl-1-butene 
D)  none of these

Question 3

Which of the following is true of the non-cyclic portion of vitamin A?

Accepted Answer

A)  It contains 4 double bonds, all in the cis configuration. 
B)  It contains 4 double bonds, all in the trans configuration. 
C)  It contains 4 double bonds, which alternate cis, trans, cis, trans. 
D)  None of the above is true. 
A)  It contains 4 double bonds, all in the cis configuration. 
B)  It contains 4 double bonds, all in the trans configuration. 
C)  It contains 4 double bonds, which alternate cis, trans, cis, trans. 
D)  None of the above is true.

Question 4

Which product is formed by the chlorination of 2-methyl-1-butene?

Accepted Answer

A)  1,1-dichloro-2-methylbutane 
B)  1,2-dichloro-2-methylbutane 
C)  2-chloro-2-methylbutane 
D)  1-chloro-2-methylbutane 
A)  1,1-dichloro-2-methylbutane 
B)  1,2-dichloro-2-methylbutane 
C)  2-chloro-2-methylbutane 
D)  1-chloro-2-methylbutane

Question 5

Which of the listed products will be formed in the following reaction?

Accepted Answer

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

Question 6

Which of the following compounds, all of which have the molecular formula C6H12, has cis and trans isomers?

Accepted Answer

A)  2-methyl-1-pentene 
B)  2-methyl-2-pentene 
C)  3-methyl-2-pentene 
D)  They all have cis-trans isomers. 
A)  2-methyl-1-pentene 
B)  2-methyl-2-pentene 
C)  3-methyl-2-pentene 
D)  They all have cis-trans isomers.

Question 7

Which of the following is true of the six atoms of ethylene?

Accepted Answer

A)  Four atoms lie in the same plane, but two atoms are not in this plane. 
B)  All six atoms lie in the same plane. 
C)  The carbon atoms have a tetrahedral geometry so the C−C−H angles are approximately 109°. 
D)  none of the above 
A)  Four atoms lie in the same plane, but two atoms are not in this plane. 
B)  All six atoms lie in the same plane. 
C)  The carbon atoms have a tetrahedral geometry so the C−C−H angles are approximately 109°. 
D)  none of the above

Question 8

A student named a particular compound 2-ethyl-3-methyl-2-butene. Assuming that the student's choice actually corresponded to the correct distribution of the double bond and the substituents, what is the correct IUPAC name for this compound?

Accepted Answer

A)  2-ethyl-3-methyl-2-butene 
B)  3,4-dimethyl-3-pentene 
C)  2,3-dimethyl-2-pentene 
D)  2,3-dimethyl-1-pentene 
A)  2-ethyl-3-methyl-2-butene 
B)  3,4-dimethyl-3-pentene 
C)  2,3-dimethyl-2-pentene 
D)  2,3-dimethyl-1-pentene

Question 9

Which of the following occurs when rhodopsin absorbs light?

Accepted Answer

A)  The less stable 11,12-cis isomer is converted to the more stable trans isomer. 
B)  The less stable 11,12-trans isomer is converted to the more stable cis isomer. 
C)  The more stable 11,12-cis isomer is converted to the less stable trans isomer. 
D)  The more stable 11,12-trans isomer is converted to the less stable cis isomer. 
A)  The less stable 11,12-cis isomer is converted to the more stable trans isomer. 
B)  The less stable 11,12-trans isomer is converted to the more stable cis isomer. 
C)  The more stable 11,12-cis isomer is converted to the less stable trans isomer. 
D)  The more stable 11,12-trans isomer is converted to the less stable cis isomer.

Question 10

Which product is formed by the bromination of cyclohexene?

Accepted Answer

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

Question 11

Which of the listed products will be formed in the following reaction?

Accepted Answer

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

Question 12

What is the name of the lightest hydrocarbon which has cis and trans isomers?

Accepted Answer

A)  1-butene 
B)  2-butene 
C)  1,2-dimethylcyclopropane 
D)  propene 
A)  1-butene 
B)  2-butene 
C)  1,2-dimethylcyclopropane 
D)  propene

Question 13

Which of the following compounds is a natural ripening agent for fruits?

Accepted Answer

A)  ethane 
B)  ethylene 
C)  acetylene 
D)  none of these 
A)  ethane 
B)  ethylene 
C)  acetylene 
D)  none of these

Question 14

What is the configuration of each of the alkenes shown below?

Accepted Answer

A)  (i) cis (ii) cis 
B)  (i) trans (ii) trans 
C)  (i) cis (ii) trans 
D)  (i) trans (ii) cis 
A)  (i) cis (ii) cis 
B)  (i) trans (ii) trans 
C)  (i) cis (ii) trans 
D)  (i) trans (ii) cis

Question 15

What type of alcohol is formed by the hydration of 2-butene?

Accepted Answer

A)  primary 
B)  secondary 
C)  tertiary 
D)  None of these, the product is not an alcohol. 
A)  primary 
B)  secondary 
C)  tertiary 
D)  None of these, the product is not an alcohol.

Question 16

Chloroprene, which is the monomer used to make neoprene rubber, is one of several monochloro derivatives of 1,3-butadiene. How many monochloro derivatives of 1,3-butadiene are there? (Be sure to account for cis-trans isomers.)

Accepted Answer

A)  2 
B)  3 
C)  4 
D)  5 
A)  2 
B)  3 
C)  4 
D)  5

Question 17

Consider the substance represented by the following model.   The physical properties of this substance would most closely represent the corresponding member of which functional group class?

Accepted Answer

A)  alkyne 
B)  alcohol 
C)  aldehyde 
D)  carboxylic acid 
A)  alkyne 
B)  alcohol 
C)  aldehyde 
D)  carboxylic acid

Question 18

Four patterns can be noted for certain organic reactions;
Pattern 1: Add a proton.
Pattern 2: Take a proton away.
Pattern 3: Reaction between an electrophile and nucleophile to form a new covalent bond.
Pattern 4: Reaction of proton donor with a carbon to carbon double bond to from a new covalent bond.
-To which pattern does the following reaction belong?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 19

Consider the alkyne counterpart of the following compound.   Which of the following would characterize this alkyne?

Accepted Answer

A)  C3H6 
B)  CH3C   CH 
C)    
D)  both a and b 
E)  a, b and c 
A)  C3H6 
B)  CH3C   CH 
C)    
D)  both a and b 
E)  a, b and c

Question 20

How many stereoisomers are possible for 1,4,6-octatriene?

Accepted Answer

A)  2 
B)  4 
C)  8 
D)  16 
A)  2 
B)  4 
C)  8 
D)  16

Exam 12: Alkenes and Alkynes

Which of the following compounds will not produce methylcyclopentane after catalytic hydrogenation?

A student wanted to use the branched groups, isobutyl, sec-butyl, and tert-butyl when naming alkenes, but was told not to. What is the correct IUPAC name for the compound the student called sec-butylethene?

Which of the following is true of the non-cyclic portion of vitamin A?

Which product is formed by the chlorination of 2-methyl-1-butene?

Which of the listed products will be formed in the following reaction?

Which of the following compounds, all of which have the molecular formula C6H12, has cis and trans isomers?

Which of the following is true of the six atoms of ethylene?

A student named a particular compound 2-ethyl-3-methyl-2-butene. Assuming that the student's choice actually corresponded to the correct distribution of the double bond and the substituents, what is the correct IUPAC name for this compound?

Which of the following occurs when rhodopsin absorbs light?

Which product is formed by the bromination of cyclohexene?

Which of the listed products will be formed in the following reaction?

What is the name of the lightest hydrocarbon which has cis and trans isomers?

Which of the following compounds is a natural ripening agent for fruits?

What is the configuration of each of the alkenes shown below?

What type of alcohol is formed by the hydration of 2-butene?

Chloroprene, which is the monomer used to make neoprene rubber, is one of several monochloro derivatives of 1,3-butadiene. How many monochloro derivatives of 1,3-butadiene are there? (Be sure to account for cis-trans isomers.)

Consider the substance represented by the following model. The physical properties of this substance would most closely represent the corresponding member of which functional group class?

Consider the alkyne counterpart of the following compound. Which of the following would characterize this alkyne?

How many stereoisomers are possible for 1,4,6-octatriene?

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Which of the following compounds, all of which have the molecular formula C₆H₁₂, has cis and trans isomers?