Ncert Exercises & Solutions

10.19 How the following conversions can be carried out?

(i) Propene to propan-1-ol

(ii) Ethanol to but-1-yne

(iii) 1-Bromopropane to 2-bromopropane

(iv) Toluene to benzyl alcohol

(v) Benzene to 4-bromonitrobenzene

(vi) Benzyl alcohol to 2-phenylethanoic acid

(vii) Ethanol to propanenitrile

(viii) Aniline to chlorobenzene

(ix) 2-Chlorobutane to 3, 4-dimethylhexane

(x) 2-Methyl-1-propene to 2-chloro-2-methylpropane

(xi) Ethyl chloride to propanoic acid

(xii) But-1-ene to n-butyliodide

(xiii) 2-Chloropropane to 1-propanol

(xiv) Isopropyl alcohol to iodoform

(xv) Chlorobenzene to p-nitrophenol

(xvi) 2-Bromopropane to 1-bromopropane

(xvii) Chloroethane to butane

(xviii) Benzene to diphenyl

(xix) tert-Butyl bromide to isobutyl bromide

(xx) Aniline to phenylisocyanide

$C H_{3} — C H = C H_{2} \to (A n i - M a r k o v n i k o v$
$A d d i t i o n H B r / P r i x u d e C H_{3} — C H_{2} — C H_{2} — B r$
$P r o p e n e 1 - B r o m o p r o p a n e$

$C H_{3} — C H_{3} — C H_{3} — O H$
$P r o p a n - 1 - o l$

(ii) $C H_{3} C H_{2} O H \overset{r e d P / B r_{2}}{\to} C H_{3} C H_{2} B r \overset{M g / e t h e r}{\to} C H_{3} C H_{2} M g B r$
$E t h n o l E t h y l b r o m i d e E t h y l m a g n e s i u m$

(iii)

(iv)

(v)

(vi)

(vii) $C H_{3} — C H_{2} — O H \overset{r e d p / B r_{2}}{\to} C H_{3} — C H_{2} — B R \overset{K C N, A Q, e t h a n o l}{\to} C H_{3} — C H_{2} — C N$
$E h a n o l B r o m o e t h a n e P r o p a n e n i t r i l e$

(viii)

(ix) $C l C H_{3} C H_{3}$
$| | |$
$2 C H_{3} — C H — C H_{2} C H_{3} \to_{(w o o d y r e a c t i o n)}^{2 N a / d r y e t h e r} C H_{3} — C H_{2} — C H — C H — C H_{2} — C H_{3} + 2 N a C l$
$2 - c h l o r o b u \tan e 3, 4 - d i m e t h y l h e x a n e$

(x) $C H_{3} C H_{3}$
$| |$
$C H_{3} — C = C H_{3} \to_{(M a r k o v n i k o v)}^{H C l} C H_{3} — C = C H_{3}$
$2 - M e t h y l - l - p r o p e n e 2 - c h l o r o - 2 - m e t h y l p r o p a n e$

(xi) $C H_{3} — C H_{3} — C l \to (n u c l e o p h i l i e$
$s u b t i t u t i o n) K C N, a q e t h a n o l C H_{3} — C H_{2} — C N + K C l$

(xii) $C H_{3} — C H_{2} — C H = C H_{2} \to (A n t i - M a r k o v n i k o v$
$a d d i t i o n) H B r / P e r o x i d e C H_{3} — C H_{2} — C H_{2} — C H_{2} — B r$
$B u t - 1 - e n e$

(xiii) $C l$
$|$
$C H_{3} — C H — C H_{3} \to_{(D e h y d r o h a \log e n a t i o n)}^{K O H (a l c) / ∆} C H_{3} — C H = C H_{2} + H C l$
$2 - C h l o r o p r o p a n e P r o p a n e$

(xiv) $O H O$
$| | |$
$C H_{3} — C H — C H_{3} \to_{(o x i d a t i o n)}^{C r O_{3}} C H_{3} — C — C H_{3}$
$l s o p r o p l y a l c h o l P r o p a n o n e$

(xv)

(xvi) $B r$
$|$
$C H_{3} — C H — C H_{3} \to_{D e h y d r o h a \log e n a t i o n}^{K O H (a l c) / ∆} C H_{3} — C H — C H_{2} + H B r$
Propene

(xvii) $C H_{3} — C H_{2} — C l \to_{(w u r t z r e a c t i o n)}^{2 N a / d r y e t h e r} C H_{3} — C H_{2} — C H_{2} — C H_{3} + 2 N s C l$
$C h l o r o e t h a n e B u \tan e$

(xviii)

(xix) $B r$
$|$
$C H_{3} — C — C H_{3} \to_{(D e h y d r o h a \log e n a t i o n)}^{K O H (a l c)} C H_{3} — C = C H_{2} \to_{(A n t i - M a r k o v n i k o v}^{H B r / P e r o x i d e} C H_{3} — C H — C H_{2} — B r$
$| | |$
$B r C H_{3} l s o b u t y b r o m i d e C H_{2}$
$T e r t - B u t y l b r o m i d e 2 - M e t h l p r o p e n e$

(xx)

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