Assume that the four pairs of reactions below are carried out under otherwise id

Question

Assume that the four pairs of reactions below are carried out under otherwise identical conditions. For each pair, select the process that occurs at a faster rate. For additional practice, ensure that you could rationalize your selections with drawings and brief comments. O LIOE+bromoethane ->SN2 product O LINHEt+ bromoethane->SN2 product Pair 1 O NaSR+ 1-iodopropane ->SN2 product O NaOR+ 1-iodopropane >SN2 product Pair 2 O O NaSR+ 1-iodopropane -> SN2 product Pair 3 NaSR+ 2-iodopropane->SN2 product O O NaSR+ 1-iodopropane -> SN2 product Pair 4 NaSR+1-chloropropane->SN2 product NaSR + 1-chloropropane-

Explanation / Answer

A Quick Concept:

Now coming to the question:

(a) In LiOEt and LiNHEt, O and N are the donor atoms. Since the elctronegativity of O is higher than N therefore the reaction involving LiNHEt will occur at a faster rate.

(b) Similar to above S has lower electronegativity than O. Therefore the rate of the reaction involving NaSR is faster.

(c) Due to steric hinderance reaction involving 1-iodopropane will be faster.

(d) Here I- is weak base and hence better leaving group than Cl-. Hence reaction invoving I- will be faster.

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