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Assignment 15 - SN1 and SN2 - 2017

1. The document discusses SN1 and SN2 reaction mechanisms. It provides examples of reactions that proceed by either SN1 or SN2 pathways and asks students to identify which mechanism is operative based on factors like the reaction rate and the substituents involved. It also asks students to rank reaction rates and predict products based on the mechanism. 2. Topics covered include the effects of the substrate structure on the reaction pathway, solvent effects, predicting relative reaction rates, determining absolute configuration of products, and explaining reaction outcomes based on the mechanism. Students are asked critical thinking questions to assess their understanding of SN1 and SN2 reactions.

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160 views

Assignment 15 - SN1 and SN2 - 2017

1. The document discusses SN1 and SN2 reaction mechanisms. It provides examples of reactions that proceed by either SN1 or SN2 pathways and asks students to identify which mechanism is operative based on factors like the reaction rate and the substituents involved. It also asks students to rank reaction rates and predict products based on the mechanism. 2. Topics covered include the effects of the substrate structure on the reaction pathway, solvent effects, predicting relative reaction rates, determining absolute configuration of products, and explaining reaction outcomes based on the mechanism. Students are asked critical thinking questions to assess their understanding of SN1 and SN2 reactions.

Uploaded by

DPSI Parent Body
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Chemistry 2500 (Fall 2017): Assignment #15 – SN1 and SN2

1. The following reaction:


R3CBr + NaCN R3CCN + NaBr

can proceed via 2 different pathways (Path A, Path B), each of which are outlined
below.

Path A:
NaCN
R3CBr R3C+ + Br- R3CCN + NaBr

Path B:
NaCN R3
R3CBr NC C Br R3CCN + NaBr

a) Briefly explain why Path A is operative when R = CH3, but Path B is operative
when R = H.

b) Which of the two pathways would you expect to require a polar solvent? Why?

2. Which of the following reactions would you expect to react faster? Why?

(H3C)3CBr + CH3OH (H3C)3COCH3

(H3C)2CHBr + CH3OH (H3C)2CHOCH3

3. For each of the following compounds rank the expected order of reaction rate for an
SN1 mechanism:

I I I CH 3

PhCH2I
4. For each of the following compounds rank the expected order of reaction rate for an
SN2 mechanism:

CH3Br Br Br

Br

5. R-3-bromononane is allowed to stir with excess NaI in acetone at room temperature.


Additional experiments establish that the rate of the reaction is dependent upon the
concentration of both the bromononane and the sodium iodide.

a) Write an equation for this reaction.


b) What is the expected absolute configuration of the product?
c) Suggest a reason why if the product is isolated after 2 hours only one enantiomer
is present, but if the mixture is allowed to stir for 48 hours a racemic mixture is
obtained.

6. Of the following pairs of reactions, which one (if either) is faster. Explain your
reasoning. Be sure to indicate which mechanism is operative.

a)

CH3 O H/ H 2 O
A) CH2 Cl

CH3 O H/ H 2 O
B) CH2 Cl

b)
HO-
Cl

Cl HO-
C
H2
c)
Cl CH3O-

Cl CH3S -

d)
Cl CH3S -

Cl CH3S -

7. The following reaction proceeds via an SN2 mechanism. Explain why the absolute
configuration of both the starting material and product is R.

H H
+ NaOH
C C
Cl - NaI Cl
I HO
H3C CH3

8. For each of the following compounds rank the expected order of reaction rate for an
SN1 mechanism. No explanation is required. (4 points)

Br Br Br
PhCH2Br

9. Methyl bromomethyl ether (depicted below) is a good substrate for both SN1 and SN2
reactions. Why?
O Br
H3 C C
H2
10. For the following four compounds, rank the molecules in order of rate of reaction in
the SN1 process. Explain your reasoning.

Br

Br

Cl Cl

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