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Elementary Organic Chemistry Quiz 6: SN2 Reactions, Quizzes of Organic Chemistry

A november 3, 2008 in-class quiz for chemistry 231, elementary organic chemistry, focusing on sn2-type reactions. Students are asked to write a rate expression, draw a transition state diagram, explain why the sn2 mechanism is followed, rank organohalides and nucleophiles in order of reactivity, and draw the major organic product.

Typology: Quizzes

Pre 2010

Uploaded on 08/04/2009

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NAME: November 3, 2008
Chemistry 231 – Elementary Organic Chemistry
In-Class Quiz -- #6
1. (20 pts total) Consider the following S
N
2-type reaction between iodomethane and
ammonia:
CH
3
—I + :NH
3
[CH
3
—NH
3
]
+
+ I
-
a. (4 pts) Given that this is a second-order process (Hint: It is
a concerted process), write a reasonable rate expression
for the above reaction. Place your answer in the box
provided.
b. (8 pts) In the space provided below, draw a three-dimensional diagram showing
the transition state for the S
N
2-type reaction between iodomethane and
ammonia. Be certain to indicate both the geometry and bond angles at carbon in
your model.
c. (8 pts) Why do you think that this process proceeds by way of the S
N
2 reaction
mechanism? Be concise.
Rate =
pf2

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NAME: November 3, 2008

Chemistry 231 – Elementary Organic Chemistry

In-Class Quiz --

  1. (20 pts total) Consider the following SN2-type reaction between iodomethane and ammonia:

CH 3 —I + :NH 3  [CH 3 —NH 3 ]+^ + I-

a. (4 pts) Given that this is a second-order process (Hint: It is a concerted process), write a reasonable rate expression for the above reaction. Place your answer in the box provided.

b. (8 pts) In the space provided below, draw a three-dimensional diagram showing the transition state for the SN2-type reaction between iodomethane and ammonia. Be certain to indicate both the geometry and bond angles at carbon in your model.

c. (8 pts) Why do you think that this process proceeds by way of the SN2 reaction mechanism? Be concise.

Rate =

  1. (5 pts) Rank each of the following organohalides in order of increasing reactivity via the SN2 mechanism (1 = most reactive and 4 = least reactive).

Br Br I Br

________ ________ ________ ________

  1. (5 pts) Rank each of the following nucleophiles in order of increasing reactivity via the SN2 mechanism (1 = most reactive and 4 = least reactive).

NaN 3 NaO 2 CCH 3 NaCN NaI

________ ________ ________ ________

  1. (5 pts) In the space provided below, draw the structure of the major organic product expected. If no reaction occurs, write “No reaction”. Be certain to indicate stereochemistry, where applicable.

Br (^) NaSCH 3 DMSO

OH (^) NaCl Acetone