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PROBLEM 7.35

Expert-verified
Organic Chemistry
Found in: Page 282

Short Answer

Question: Determine the mechanism and draw the products of each reaction. Include the stereochemistry at all stereogenic centers.

a.

b.

c.

d.

ANSWER

a. The reaction favors the SN2 mechanism.

Products of (a)

b.The reaction favors the SN2 mechanism.

Products of (b)

c.The reaction favors the SN1 mechanism.

Products of (c)

d.The reaction favors the SN2 mechanism

Products of (d)

See the step by step solution

Step by Step Solution

Determination of the reaction mechanism

The following few points are to be considered to determine the reaction mechanism:

  • Substrates: For methyl, halide the reaction is SN2 ; for halides the reaction is SN1 . However, for halides, the reaction takes either of the two mechanisms depending on other factors.

  • Nucleophiles: Strong nucleophiles favor SN2, and weak nucleophiles favor SN1 reaction mechanism.

 Stereogenic centers

Such carbon centers with all four different groups different at which the spatial arrangement of molecules can be different to form stereoisomers are called stereogenic centers

Determination of the reaction pathway

a. The reaction mechanisms along with the stereochemistry are shown below:

Both the alkyl halide and the nucleophile favor the SN2 mechanism. The products of the given reaction are as follows

Products of (a)

b.The alkyl halide is ; hence, it can undergo either SN1 or SN2 mechanism. N3- is a strong nucleophile and favors SN2 mechanism. Hence, the reaction favors the SN2 mechanism.

In SN2 mechanism, inversion in the products occurs, i.e., as the leaving group is up, the nucleophile attacks from below.

The products of the given reaction are shown below:

Products of (b)

c. Both the given alkyl halide and the weak nucleophile favor the SN1 mechanism. The products of the given reaction are shown below:

Products of (c)

d. Both the alkyl halide and the nucleophile favor the SN1 mechanism. The products of the given reaction are shown below:

Products of (d)

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