Write Brief Answer · Q5
Q.Identify A, B, C and D: ethanoic acid, treated with
(i) SOCl2, gives A; A, treated with
(ii) H2/Pd-BaSO4 (Rosenmund reduction), gives B; B, treated with
(iii) dilute NaOH (warm), gives C; C, on further gentle heating with loss of water, gives D.
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Start your 14-day free trial to unlock the full solution →Step 1. Ethanoic acid + SOCl2 (i) replaces the acid's -OH with -Cl (Section 12.12.B.1/12.14.2.1) to give A = acetyl chloride, CH3COCl, + SO2 + HCl.
Step 2. A + H2/Pd-BaSO4 (ii), the Rosenmund reduction (Section 12.3.B.1), reduces the acid chloride selectively to the ALDEHYDE (the poisoned Pd catalyst stops the reduction short of the alcohol): B = acetaldehyde, CH3CHO, + HCl.
Step 3. B, warmed with dilute NaOH (iii), undergoes aldol ADDITION (Section 12.5.E.1): two acetaldehyde molecules combine via the base-generated enolate, giving C = acetaldol (3-hydroxybutanal), CH3-CH(OH)-CH2-CHO. …
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