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Question 72 of 88

Q.(A) Write the structure of phenylmethanamine.

(1)
(B) Write chemical equation for the following:
(4)
(i) Gatterman–Koch formylation
(ii) Rosenmund reduction
(iii) Fischer esterification
(iv) Hell–Vohlard–Zelinsky reaction OR (A) What are amines?
(1)
(B) How will you convert
(4)
(i) calcium acetate to acetaldehyde
(ii) acetone to acetone cynohydrin
(iii) sodium acetate to methane
(iv) benzoic acid to m-bromobenzoic acid?
Maharashtra MsbshseMaharashtra HSC (MSBSHSE) Board 2019Subjective· 5mImportance★★★★★
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Benzylamine's structure, plus four classic named reactions producing an aldehyde, an aldehyde, an ester, and an α\alpha-halo acid respectively.

(A) Phenylmethanamine (benzylamine): C6H5−CH2−NH2C_6H_5-CH_2-NH_2 — a primary amine with the −NH2-NH_2 group on a CH2CH_2 attached to the benzene ring (not directly on the ring, so it behaves as an aliphatic amine).

(B) Reactions:

  1. Gatterman–Koch formylation: benzene is treated with CO and HCl in the presence of anhydrous AlCl3AlCl_3/CuClCuCl under pressure, introducing a −CHO-CHO group directly onto the ring: C6H6+CO+HCl→CuClanhyd. AlCl3C6H5CHO+HClC_6H_6 + CO + HCl \xrightarrow[CuCl]{anhyd.\ AlCl_3} C_6H_5CHO + HCl
  2. Rosenmund reduction: an acyl chloride is selectively reduced to an aldehyde using H2H_2 over a poisoned palladium catalyst (Pd/BaSO4_4, poisoned with sulphur/quinoline to prevent over-reduction to alcohol): C6H5COCl+H2→Pd/BaSO4C6H5CHO+HClC_6H_5COCl + H_2 \xrightarrow{Pd/BaSO_4} C_6H_5CHO + HCl
  3. Fischer esterification: a carboxylic acid and alcohol condense in the presence of an acid catalyst (conc. H2SO4H_2SO_4/dry HCl) to give an ester: CH3COOH+C2H5OH⇌ΔH2SO4CH3COOC2H5+H2OCH_3COOH + C_2H_5OH \underset{H_2SO_4}{\overset{\Delta}{\rightleftharpoons}} CH_3COOC_2H_5 + H_2O
  4. Hell–Volhard–Zelinsky (HVZ) reaction: a carboxylic acid with an α\alpha-hydrogen is halogenated at the α\alpha-carbon using Cl2/Br2Cl_2/Br_2 in the presence of red phosphorus: CH3CH2COOH+Br2→red PCH3CHBrCOOH+HBrCH_3CH_2COOH + Br_2 \xrightarrow{red\ P} CH_3CHBrCOOH + HBr OR alternative: (A) Amines are organic derivatives of ammonia (NH3NH_3) obtained by replacing one, two, or three hydrogen atoms with alkyl/aryl groups, classified as primary (1°), secondary (2°) or tertiary (3°) amines. (B) Conversions: …

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