Complete the following:
Reduction of $P h C H O$ with the following:
I, Tollens reagent
ii. $Z n H C I$
iii. $L A H$
iv. Clemmensen's reduction $(Z n (H g) / c o n c . H C I)$
v. Wolff-Kishner reduction $(N H_{2} N H_{2}$ + Glycol + $O^{-}$ $H)$
vi. Two moles of $P h C H O$ with $Z n + H C l$

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Solution

$(i) T o l l e n - --- \to P h - C O O H$
$P h C H O$ $(i i) Z n / H C l - ---- \to P h - C H_{3}$
$(i i i) L A H - -- \to P h - C H_{2} O H$
$(i v) Z n / H g - --- \to H C l P h - C H_{3}$

$(v) N_{2} H_{4}, O H^{-} - ------ \to P h - C H_{3}$
$(v i) Z n / H C l - ---- \to 2 P h - C H_{3}$

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Similar questions

	Column I		Column II
(A)	$R C O C H_{3} Z n - H g - --- \to H C l R C H_{2} C H_{3}$	(i)	Wolff-Kishner reduction
(B)	$2 C_{6} H_{5} C H O N a O H - --- \to C_{6} H_{5} C O O N a + C_{6} H_{5} C H_{2} O H$	(ii)	Clemmensen reduction
(C)	$C_{6} H_{6} + C H_{3} C O C l A n h . - -- \to A l C l_{3} C_{6} H_{5} C O C H_{3}$	(iii)	Friedel-Crafts reaction
(D)	$C_{6} H_{10} O (i) N H_{2} N H_{2} - ------------- \to K O H / e t h y l e n e g l y c o l, Δ C_{6} H_{12} + N_{2}$	(iv)	Cannizzaro reaction

Reduction of carbonyl group into –CH₂ in presence of Zn-Hg/HCl is an example of: