MyQuestionIcon

1

You visited us 1 times! Enjoying our articles? Unlock Full Access!

Curtius and Hofmann Rearrangements

How will you ...

Question

How will you convert

(i) ethanoic acid into methanamine?

(ii) hexanenitrile into 1-aminopentane?

(iii) Methanol to ethanoic acid?

(iv) ethanamine into methanamine?

(v) Ethanoic acid into propanoic acid

(vi) Methanamine into ethanamine?

(vii) nitromethane into dimethylamine?

(viii) propanoic acid into ethanoic acid?

Open in App

Solution

(i) Ethanoic acid into methanamine

$C H_{3} C O O H E t h a n o i c a c i d S O C l_{2} - --- \to C H_{3} C O C l E t h a n o y l c h l o r i d e N H_{3} (e x c e s s) - ------- \to C H_{3} C O N H_{2} E t h a n a m i d e B r_{2} / K O H - ---------------- \to H o f m a n n b r o m i d e r e a c t i o n C H_{3} N H_{2} M e t h a n a m i n e$

(ii) Hexane nitrile into 1-aminopentane

$C H_{3} (C H_{2})_{4} C N H e x a n a e n i t r i l e H_{3} O^{+} p a r t i a l - ------- \to H y d r o l y s i s C H_{3} (C H_{2})_{4} C O N H_{2} H e x a n a m i d e B r_{2} / K O H - ----- \to C H_{3} (C H_{2})_{4} N H_{2} 1 - a m i n o p e n t a n e$

(iii) Methanol to ethanoic acid

$C H_{3} O H M e t h a n o l P C l_{5} - -- \to C H_{3} C l C h l o r o m e t h a n e K C N - -- \to C H_{3} C N E t h a n e n i t r i l e H_{3} O^{+} - -- \to C H_{3} C O O H E t h a n o i c a c i d$

(iv) Ethanamine into methanamine

$C H_{3} C H_{2} N H_{2} E t h a n a n m i n e H O N O - --- \to C H_{3} C H_{2} O H E t h a n o l [O] - --------- \to K_{2} C r_{2} O_{7} / H_{2} S O_{4} C H_{3} C H O [O] - --------- \to K_{2} C r_{2} O_{7} / H_{2} S O_{4} C H_{3} C O O H N H_{3} - -- \to H e a t C H_{3} C O N H_{2} E t h a n a n m i d e B r_{2} / K O H - ----- \to C H_{3} N H_{2} M e t h a n a m i n e$

(v) Ethanoic acid into propanoic acid

$C H_{3} C O O H E t h a n o i c a c i d L i A l H_{4} - --- \to C H_{3} C H_{2} O H E t h a n o l P / I_{2} - -- \to C H_{3} C H_{2} I I o d o e t h a n e K C N - -- \to C H_{3} C H_{2} C N P r o p a n e n i t r i l e H_{2} O / H^{+} - ---- \to C H_{3} C H_{2} C O O H P r o p a n o i c a c i d$

(vi) Methanamine into ethanamine

$C H_{3} N H_{2} M e t h a n a m i n e H O N O - ------ \to - N_{2}, - H_{2} O C H_{3} O H M e t h a n o l P / I_{2} - -- \to C H_{3} I M e t h y l i o d i d e K C N - -- \to C H_{3} C N M e t h y l n i t r i l e 4 [H] - -------------- \to N a / C_{2} H_{5} O H / R e d u c t i o n C H_{3} C H_{2} N H_{2} E t h a n a m i n e$

(vii) Nitromethane into dimethyl amine

$C H_{3} N O_{2} N i t r o m e t h a n e S n / H c l - --- \to [H] C H_{3} N H_{2} A m i n o m e t h a n e C H C I_{3} / K O H - ------- \to C H_{3} N C M e t h y l i s o c y a n i d e N a / C_{2} H_{5} O H - ------- \to [H] C H_{3} N H C H_{3} D i m e t h l a m i n e$

(viii) Propanoic acid into ethanoic acid
$C H_{3} C H_{2} C O O H P r o p a n o i c a c i d N H_{3} / H e a t - ----- \to C H_{3} C H_{2} C O N H_{2} P r o p a n a m i d e B r_{2} / K O H - ----- \to C H_{3} C H_{2} N H_{2} E t h y l a m i n e H O N O - ------ \to - N_{2}, - H_{2} O C H_{3} C H O E t h a n o l K_{2} C r_{2} O_{7} / H_{2} S O_{4} - --------- \to [O] C H_{3} C H O E t h a n a l K_{2} C r_{2} O_{7} / H_{2} S O_{4} - --------- \to [O] C H_{3} C O O H E t h a n o i c a c i d$

Suggest Corrections

thumbs-up

186

Similar questions

How will you convert ethanoic acid into methanamine?

Q. How will you convert-

(a) Ethanoic acid into propanoic acid

(b) Propanoic acid into ethanoic acid

Q. How will you convert the following?
(i) Nitrobezene into aniline.
(ii) Ethanoic acid into methanamine.
(iii) Aniline into N-phenylethanamide.
(Write the chemical equations involved).

Q. Which of the following decreasing order of acidic strength of

(I)

methanoic acid,

(I I)

(I I I)

propanoic acid, and

(I V)

butanoic acid, is correct?

Draw the structures for the following compounds :
(a) Ethanoic acid (b) Propanoic acid

View More

Join BYJU'S Learning Program

explore_more_icon

Explore more

Curtius and Hofmann Rearrangements

Standard XII Chemistry

Join BYJU'S Learning Program

CrossIcon