Question

Predict the products of the following reactions:

(a) ${\mathbf{\text{excess\hspace{0.17em}\hspace{0.17em}NH}}}_{\mathbf{\text{3}}}\mathbf{+}\mathbf{\text{\hspace{0.17em}\hspace{0.17em}Ph}}\mathbf{-}{\mathbf{\text{CH}}}_{\mathbf{\text{2}}}{\mathbf{\text{CH}}}_{\mathbf{\text{2}}}{\mathbf{\text{CH}}}_{\mathbf{\text{2}}}\mathbf{\text{Br}}\mathbf{\to }$

(b)$\mathbf{1}\mathbf{-}\mathbf{\text{bromopentane}}\underset{\begin{array}{l}{\mathbf{\text{(2)LiAlH}}}_{\mathbf{\text{4}}}\\ {\mathbf{\text{(3)H}}}_{\mathbf{\text{3}}}{\mathbf{\text{O}}}^{\mathbf{\text{+}}}\end{array}}{\overset{{\mathbf{\text{(1)NaN}}}_{\mathbf{\text{3}}}}{\mathbf{\to }}}$

(c)

(d) $\mathbf{\text{product\hspace{0.17em}\hspace{0.17em}from\hspace{0.17em}\hspace{0.17em}part\hspace{0.17em}\hspace{0.17em}c}}\stackrel{\mathbf{\text{heat}}}{\mathbf{\to }}$

(e)

(f) $\mathbf{\text{product\hspace{0.17em}\hspace{0.17em}from\hspace{0.17em}\hspace{0.17em}part\hspace{0.17em}\hspace{0.17em}e}}\underset{\mathbf{\text{(3)heat}}}{\overset{\begin{array}{l}{\mathbf{\text{(1)excessCH}}}_{\mathbf{\text{3}}}\mathbf{\text{I}}\\ {\mathbf{\text{(2)Ag}}}_{\mathbf{\text{2}}}\mathbf{\text{O}}\end{array}}{\mathbf{\to }}}$

(g)

(h)

(i)

(j) $\mathbf{\text{product\hspace{0.17em}\hspace{0.17em}from\hspace{0.17em}\hspace{0.17em}part\hspace{0.17em}\hspace{0.17em}i}}\underset{{\mathbf{\text{(2)H}}}_{\mathbf{\text{3}}}{\mathbf{\text{O}}}^{\mathbf{\text{+}}}}{\overset{{\mathbf{\text{(1)LiAlH}}}_{\mathbf{\text{4}}}}{\mathbf{\to }}}$

(k)

(l)

Short answer

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

(k)

(l)

Step-by-step solution

Prediction of products

(a) (3-bromopropyl)benzene on treatment with excess ammonia gives the product as 3-phenylpropan-1-amine.

reaction a

(b) 1-bromopentane on treatment with sodium azide forms 1-azidopentane, which on further reduction with lithium aluminum hydride gives the final product as pentan-1-amine.

reaction b

(c) 1-methylpiperidine reacts with hydrogen peroxide to give the product as 1-methylpiperidine 1-oxide.

reaction c

(d) 1-methylpiperidine 1-oxide on heating gives the product as N-methyl-N-(pent-4-en-1-yl)hydroxylamine.

reaction d

(e) Octahydro-1H-quinolizine on treatment with excess methyl iodide gives the initial product as 5-methyldecahydroquinolizin-5-ium, which on further reaction with silver oxide followed by heating gives the final product as 2-(but-3-en-1-yl)-1-methylpiperidine.

reaction e

(f) 2-(but-3-en-1-yl)-1-methylpiperidine on treatment with excess methyl iodide gives the initial product as 2-(but-3-en-1-yl)-1,1-dimethylpiperidin-1-ium, which on further reaction with silver oxide followed by heating gives the final product as N,N-dimethylnona-1,8-dien-5-amine.

reaction f

(g) Piperidine on treatment with sodium nitrite in presence of hydrochloric acid gives the product as 1-nitrosopiperidine.

reaction g

(h) Nitrobenzene on treatment with zinc in presence of hydrochloric acid gives the product as aniline.

reaction h

(i) 2-cyclohexylacetyl chloride on treatment with methylamine in presence of pyridine gives the product as 2-cyclohexyl-N-methylacetamide.

reaction i

(j) 2-cyclohexyl-N-methylacetamide on reduction with lithium aluminum hydride gives the final product as 2-cyclohexyl-N-methylethanamine.

reaction j

(k) (E)-N-(heptan-3-ylidene)methanamine on reduction with lithium aluminum hydride gives the final product as N-methylheptan-3-amine.

reaction k

(l) 2-methyl-3-phenylpropanenitrile on reduction with lithium aluminum hydride gives the final product as 2-methyl-3-phenylpropan-1-amine.

reaction l