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Grade: 12th pass
Consider thiol anion (RS^T) and alkoxy anion (RO^T).
Which of the following statements is correct ?
a. RS^T is less basic but more nucleophilic than RO^T
b. RS^T is more basic and more nucleophilic than RO^T
c. RS^T is more basic but less nucleophilic than RO^T
d. RS^T is less basic and less nucleophilc than RO^T
5 years ago

Answers : (2)

Kevin Nash
askIITians Faculty
332 Points

(a) On moving down a group, the basicity & nucleophilicity are inversely related, i.e. nucleophilicity increases while basicity decreases. i.e RS^T is more nucleophilic but less basic than RO^T. This opposite behavior is because of the fact that basicity and nucleophilicity depends upon different factors. Basicity is directly related to the strength of the H-element bond, while nuclepphilicity is indirectly related to the electronegativity of the atom to which proton is attached.

5 years ago
Dinesh Chopra
13 Points
RSH is a stronger acid than ROH since, the conjugate base is more stable ( megs charge on sulphur is more stable due to larger size). Since acid is  strong the conjugate base is weak. Also RS- being more stable is more nucleophilic in nature.
2 years ago
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