Identify product $D$ in the following reaction sequence:
$CH_3-C(CH_3)_2-CH_2-CH_2-OH$ $\xrightarrow[H_2O, \text{heat}]{K_2Cr_2O_7, H_2SO_4} A$ $\xrightarrow{SOCl_2} B$ $\xrightarrow{2(CH_3)_2NH} C$ $\xrightarrow[2. H_2O]{1. LiAlH_4, \text{diethyl ether}} D$

  • A
    $CH_3-C(CH_3)_2-CH_2-CN$
  • B
    $CH_3-C(CH_3)_2-CH_2-CH_2-N(CH_3)_2$
  • C
    $CH_3-C(CH_3)_2-CH_2-CH(N(CH_3)_2)_2$
  • D
    $CH_3-C(CH_3)_2-CH_2-CH(OH)N(CH_3)_2$

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$RCONH_2$ is converted into $RNH_2$ by means of Hofmann bromamide degradation. In this reaction,$RCONHBr$ is formed from which this reaction has derived its name. Electron donating group at phenyl activates the reaction. Hofmann degradation reaction is an intramolecular reaction.
$1.$ How can the conversion of $(i)$ to $(ii)$ be brought about?
$(A)$ $KBr$
$(B)$ $KBr + CH_3ONa$
$(C)$ $KBr + KOH$
$(D)$ $Br_2 + KOH$
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$(A)$ Formation of $(i)$
$(B)$ Formation of $(ii)$
$(C)$ Formation of $(iii)$
$(D)$ Formation of $(iv)$
$3.$ What are the constituent amines formed when the mixture of $(i)$ and $(ii)$ undergoes Hofmann bromamide degradation?
Give the answer for question $1$,$2$,and $3$.

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