Question

Suppose you were told that the above reaction was a substitution reaction but you were not told the mechanism. Evaluate the following categories to determine the reaction mechanism and then draw the structure of the major organic product.Type of alkyl halide: _________ (methyl, primary, primary benzyl, primary allyl, secondary, secondary benzyl, secondary allyl, tertiary, tertiary benzyl, tertiary allyl.)Type of nucleophile: _________ (good, moderate, poor.)Solvent: _________ (protic, aprotic.)Is the product racemic? _____ (yes, no.)

Answer 1

Answer:

The alkyl halide is secondary

The nucleophile is a poor nucleophile

The solvent is a protic solvent

The product is racemic

Explanation:

The reaction is shown in the image attached.

Alkyl halides undergo nucleophilic substitution by two mechanisms; SN1 and SN2. The particular mechanism that applies depends on;

I) structure of the alkyl halide

ii) nature of the nucleophile

iii) nature of the solvent

Looking at the reaction under review, we can see from the structure that the alkyl halide is a secondary alkyl halide. A secondary alkyl halide may undergo substitution via SN1 or SN2 mechanism depending on the conditions of the reaction.

If the nucleophile is poor, and the solvent is protic, SN1 mechanism is favoured over SN2 mechanism. Since CH3CH2OH is a poor nucleophile and ethanol is a protic solvent, we expect the reaction to proceed via SN1 mechanism leading to the formation of a racemic product.

The organic product is also shown in the second image attached.