Question

Please rank the following acid derivatives from most reactive to least reactive toward nucleophilic attacks and explain your reasoning. 1. NH2 2. Please show how you would accomplish the following synthesis. heptanoyl chloride heptanoic anhydride CI cyclopentanecarbonyl chloride 2-propyl cyclopentanecarboxylate heptanoyl chloride N-cyclohexylheptanamide OH cyclopentyl acetate cyclopentanol

Answer 1

1. Nucleophilic attack depends on the amount of . positive change generating on the centre mome the positive change, it will beasin for the nucleophile to attack and reactivity will be high. ha - Presence of cl - cis an Electron Withdrawing Groups This is the So, it will pull the reaction site (attack of elections from combony) | nucleophile a) Carbon and making it mone electropositive. This it is more reactive Betwed Between hand and - and io- It has It has oth group - wit group attached attached to A. Both are electron donating bat. through +Renesonance) groups Garniz 26

Now But, In the and hybrid structure, oxygen thas the charge. It is mone unstable than the charge on N. So, and case, it is not stable hybrid. so, nesmance will be faroused for the Ost one and -Ost one is less reactive than and one for : von there two nucleophilic centres are present There is an oxygen atom between these two. "It can show te effect .But at once it will conjugate with only one nucksphilic combonyl grapp and for that instance other nucleophilic Centre is exposed to be attacked - expod. hot - Tim exposed. . : So, it is reactive than Previous two .

Least Reactive : Mast Reactive ها (سنگر سلول ( متر . Hack " Nuc ہلہ گل Product E Product السر - , بے کا Product و سلاح ری e الا ۔ / ک Product