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Choose the Best Answer · Q18

Q.The reaction of catechol (benzene-1,2-diol) with

(i) NaOH
(ii) CH2I2 to give the cyclic product 1,3-benzodioxole (a -O-CH2-O- bridge across the two original -OH oxygens) is an example of
a) Wurtz reaction
b) cyclic reaction
c) Williamson reaction
d) Kolbe reaction
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Step 1. Catechol (benzene-1,2-diol) has two adjacent -OH groups; NaOH deprotonates BOTH to give a dianion (bis-phenoxide).

Step 2. CH2I2 (diiodomethane) presents TWO separate electrophilic carbons (well, one CH2 carbon bearing two leaving iodides) that can each be displaced in an SN2 fashion by a nucleophilic phenoxide oxygen.

Step 3. Each phenoxide oxygen displaces one of the two iodides on the same CH2I2 carbon in turn, forming two new C-O bonds and bridging the two original oxygens into a five-membered ring (the methylenedioxy/1,3-benzodioxole ring). …

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