Question 1

Which of the following alkyl halides will undergo the slowest SN2 reaction? N2 reaction?   A)  I B)  II C)  III D)  IV E)  V" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 2

Which of the following is a strong nucleophile?

Accepted Answer

A)   OH-
B)   H2O
C)   CH3OH
D)   NH4+
E)   All of these

Question 3

Predict the major product for the following reaction.

Accepted Answer

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

Question 4

Which of the following compounds will undergo the fastest SN1 reaction? N1 reaction?   A)  I B)  II C)  III D)  IV E)  Both I & IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   Both I & IV

Question 5

Rank the following compounds from most to least reactive in an SN2 reaction. N2 reaction.   A)  I>IV>II>III B)  II>I>IV>III C)  III>IV>I>II D)  I>III>II>IV E)  IV>III>I>II" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 6

Predict the product for the following reaction.
(1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN3

Accepted Answer

Question 7

Which of the following compounds has the best leaving group?

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   All of these

Question 8

Draw the transition state for the following reaction.

Accepted Answer

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

Question 9

Which of the following is a protic solvent? - B)  II- C)  III D)  IV E)  none of these" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   I-
B)   II-
C)   III
D)   IV
E)   none of these

Question 10

What substitution reaction mechanism is most likely for the following conversion? N1 B)  SN2 C)  Either SN1 or SN2 D)  None of these" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   SN1
B)   SN2
C)   Either SN1 or SN2
D)   None of these

Question 11

Consider the following SN2 reaction, N2 reaction,   Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved? A)  No effect B)  It would double the rate C)  It would triple the rate D)  It would increase four times E)  It would reduce by half" class="answers-bank-image d-inline" rel="preload" > Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?

Accepted Answer

A)   No effect
B)   It would double the rate
C)   It would triple the rate
D)   It would increase four times
E)   It would reduce by half

Question 12

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)   NaCl in water
B)   NaCl in ether
C)   HCl in water
D)   TsCl/pyridine followed by NaCl

Question 13

What is the correct structure for 2-bromo-3-methylbutane?

Accepted Answer

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

Question 14

Which of the following is the rate equation for the following reaction? CH3CH2CH2CHBrCH3 + NaN3 →\rightarrow→ CH3CH2CH2CHN3CH3 + NaBr

Accepted Answer

A)   Rate = k[CH3CH2CH2CHBrCH3]
B)   Rate = k[NaN3]
C)   Rate = k[CH3CH2CH2CHBrCH3] [NaBr]
D)   Rate = k[CH3CH2CH2CHBrCH3] [NaN3]
E)   Rate = k[CH3CH2CH2CHBrCH3]2 [NaN3]

Question 15

Provide a curved arrow mechanism for the following reaction.

Accepted Answer

The answer of Provide a curved arrow mechanism for the...

Question 16

Which of the following potential energy diagram represent an exothermic SN1 reaction? N1 reaction?   A)  I B)  II C)  III D)  IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 17

Predict the product for the following SN2 reaction. N2 reaction.   A)  I B)  II C)  III D)  IV E)  Both I & II" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   I
B)   II
C)   III
D)   IV
E)   Both I & II

Question 18

Draw the transition state for the following reaction.
(S)-1-iodo-3-methylpentane +NaSCH3

Accepted Answer

Question 19

Which of the following is a secondary alkyl halide?

Accepted Answer

A)   (CH3) 2CHCH2Cl
B)   (CH3) 2CClCH3
C)   (CH3) 2CHCHClCH3
D)   (CH3) 2CHCH2CCl(CH3) 2

Question 20

What is the electrophile in the following reaction?

Accepted Answer

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

Exam 7: Substitution Reactions

Which of the following compounds has the best leaving group?

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Consider the following SN2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH3CH2COONa is halved?

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Provide a curved arrow mechanism for the following reaction.

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Predict the product for the following SN2 reaction.

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What substitution reaction mechanism is most likely for the following conversion?

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Draw the transition state for the following reaction.

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What is the electrophile in the following reaction?

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Draw the transition state for the following reaction. (S)-1-iodo-3-methylpentane +NaSCH3

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Which of the following is a strong nucleophile?

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Predict the major product for the following reaction.

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Which of the following compounds will undergo the fastest SN1 reaction?

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Predict the product for the following reaction. (1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN3

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Which of the following is a protic solvent?

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What is the correct structure for 2-bromo-3-methylbutane?

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Which of the following is the rate equation for the following reaction? CH3CH2CH2CHBrCH3 + NaN3 →\rightarrow→ CH3CH2CH2CHN3CH3 + NaBr

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Rank the following compounds from most to least reactive in an SN2 reaction.

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Provide the reagents necessary to carry out the following conversion.

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Which of the following alkyl halides will undergo the slowest SN2 reaction?

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Which of the following potential energy diagram represent an exothermic SN1 reaction?

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Which of the following is a secondary alkyl halide?

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Consider the following S_N2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH₃CH₂COONa is halved?

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Predict the product for the following S_N2 reaction.

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Draw the transition state for the following reaction. (S)-1-iodo-3-methylpentane +NaSCH₃

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Which of the following compounds will undergo the fastest S_N1 reaction?

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Predict the product for the following reaction. (1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN₃

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Which of the following is the rate equation for the following reaction? CH₃CH₂CH₂CHBrCH₃ + NaN₃ $\rightarrow$ CH₃CH₂CH₂CHN₃CH₃ + NaBr

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Rank the following compounds from most to least reactive in an S_N2 reaction.

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Which of the following alkyl halides will undergo the slowest S_N2 reaction?

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Which of the following potential energy diagram represent an exothermic S_N1 reaction?

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