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(a) Carry out the following conversions :

(i) $P-nitrotoluene$ to $2-bromobenzoic\; acid$

(ii) Propanoic acid to acetic acid

(b) An alkene with molecular formula $C_{5}H_{10}$ on ozonolysis gives a mixture of two compounds, B and C. Compound B gives positive
Fehling test and also reacts with iodine and $NaOH$ solution. Compound C does not give Fehling solution test but forms
iodoform. Identify the compounds A, B and C.

Answers (1)

(a) (1) $P-nitrotoluene$ to $2-bromobenzoic\; acid$

(2) Propanoic acid to acetic acid

$CH_{3}CH_{2}COOH\overset{LiALH_{4}}{\rightarrow}CH_{3}CH_{2}CH_{2}OH\overset{H^{+}}{\rightarrow}CH_{3}CH= CH_{2}\xrightarrow[OH^{-}]{KMNO_{4}}CH_{3}COOH$

(b) (A) $C_{6}H_{10}-(alkene)$
$\downarrow ozonolysis$
$B+C$

B= Positive Fenling - aldehyde group $=-CHO$

= Positive Iodoform test $\Rightarrow CH_{3}CHO\; \; (B)$

C - negative testing

= positive Iodoform

=

$B=CH_{3}CHO$

$C=CH_{3}-COCH_{3}$

Posted by

Sumit Saini

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