Question

Rank the following compounds in order of decreasing reactivity in a nucleophilic acyl substitution reactions (most to least reactive from left to right in the answer)

yucuruit pun Rank the following compounds in order of decreasing reactivity in a nucleophilic acyl substitution reaction (most to least reactive from left to right in the answer): ei ole C>A>D>B A>C>D>B A>C>B>D C>A>B>D

Answer 1

DUD cm The compounds are the s ro i ce noi (A) (B) x (con (D) The the highest 'C=o' group with the election defficiency is the most reactive, Among to', 's' and i ca in most electronegative, so it will withdraw election from the carbonyl carbongt carbon atom with the highest efficiency resulting the carbonyl Carbon the most election defficient. So, the carbonyl carbon in compound (a) is the most election defficient. Hence compound (e) is the most enactive, og er se Among this estos and ester, this ester is more eractive. Due to the bigger size of mo

Date : Page : Q bate: 1 Page 1 is compared to carbon atom, the valence election of 3p orbital of 's' cannot interact good with the 2p orbital of ren. This is known as 3p-2p orbital mismatching . As a result of which is cannot donate election densitys stowards the carbonyl carbon efficiently." Where as in case of ester the comparable size of 'e' and 'o' results efficient 2p-2p. orbital interaction. Thas the valance election from 2p orbital of 'o' can donate election density efficiently towards the carbonyl

om Da Carbon atom. From this, it is clear that the carbough carbon of ester is more electron rich compared to this estos resultings this estes more reactive than estes So, compound (A) is more enactive compared to (B) and (0) Among (B) and (D), (B) has tertiary butyl group and (A) has n-butyl group. The t I effect ê. e. the election donatings ability of tertiarys butyl group is a highen compared to nobutyl group. noche y noin (t effect) So, compound (D) has less election density at the carbonyl carbon centre compared to (6) 17 m