Write structural formulae of the organic compounds 'A', 'B', 'C' and 'D' in the following sequence of reactions: 'A' $+ C H_{3} M g B r - H_{2} O \to C H_{3} C H_{2} C H (O H) C H_{3}$ -conc. $H_{2} S O_{4} \to^{'} B^{'} - B r_{2} \to^{'} C^{'} - a l c . K O H \to^{'} D^{'}$ .

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Solution

Aldehyde and ketone form alcohol with the Grignard reagent.A s a secondary alcohol is formed with a 3 carbon chain A is propanal.
2-butanol is secondary alcohol and on dehydration, with $H_{2} S O_{4}$ will form butene. the major product is B, trans- 2-butene which forms addition product bromine2,3-bromobutane (c). This forms 2-bromo but 2-ene (D) on reaction with alcoholic $K O H$ .

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Q. Write structural formulae of the organic compounds

^{'} A^{'},^{'} B^{'},^{'} C^{'}

and

^{'} D^{'}

in the following sequence of reaction.

^{'} A^{'} + C H_{3} M g B r H_{2} O - - \to C H_{3} C H_{2} C H (O H) C H_{3} c o n c . H_{2} S O_{4} - ------ \to^{'} B^{'} B r_{2} - - \to^{'} C^{'} a l c . K O H - ---- \to^{'} D^{'}

Three organic compounds A, B and C have the following molecular formulae :
A $C_{4} H_{8} O_{2}$
B $C_{4} H_{10} O$
C $C_{4} H_{8} O$
(a) Which compound contains an alcohol group? Write its name and structural formula.
(b) Which compound contains a carboxyl group? Write its name and structural formula.
(c) Which molecular formula can represent an aldehyde as well as a ketone? Write the names and structural formulae of the aldehyde and ketone represented by this molecular formula.