Aniline reacts with mixed acid $($conc. $HNO _3$ and conc. $H _2 SO _4 )$ at $288 K$ to give $P (51 \%)$,$Q (47 \%)$ and $R (2 \%)$. The major product$(s)$ of the following reaction sequence is $($are$)$
$\text { 1) } Ac _2 O \text {, pyridine } \text { 1) } Sn / HCl $
$R \xrightarrow{2) Br _2, CH _3 CO _2 H } S \xrightarrow{2) Br _2 / H _2 O \text { (excess) }} \text { major product(s) }$
$\text { 3) } H _3 O ^{+} \text {3) } NaNO _2, HCl / 273-278 K$
$\text { 4) } NaNO _2, HCl / 273-278 K \quad \text { 4) } H _3 PO _2$
$\text { 5) } EtOH , \Delta$
$\text { 1) } Ac _2 O \text {, pyridine } \text { 1) } Sn / HCl $
$R \xrightarrow{2) Br _2, CH _3 CO _2 H } S \xrightarrow{2) Br _2 / H _2 O \text { (excess) }} \text { major product(s) }$
$\text { 3) } H _3 O ^{+} \text {3) } NaNO _2, HCl / 273-278 K$
$\text { 4) } NaNO _2, HCl / 273-278 K \quad \text { 4) } H _3 PO _2$
$\text { 5) } EtOH , \Delta$
- A
- B
- C
- D
IIT 2018, Advanced
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