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Q.Write only chemical equations for the following changes:

(i) Butanoic acid from Butan-1-ol
(ii) Butanoic acid from Butanal
(iii) 3-Nitrobenzoic acid from 3-Nitrobromobenzene
(iv) Phenyl ethanoic acid from Benzyl alcohol
(v) Acetamide from Acetic acid OR A carboxylic acid 'B' and an alcohol 'C' was obtained after hydrolysis of an organic compound 'A' (molecular formula C8H16O2C_8H_{16}O_2) with dilute sulphuric acid. 'B' is produced on oxidation of 'C' with chromic acid. But-1-ene is obtained on dehydration of 'C'. Identify 'A', 'B' and 'C'. Write chemical equations for all the reactions involved.
Uttar Pradesh UpmspUP Board (UPMSP) Intermediate 2024Subjective· 5mImportance★★★★★
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Oxidations give butanoic acid (i, ii); a nitrile route builds the –COOH on the aromatic ring (iii) and the extra carbon of phenylethanoic acid (iv); acetamide comes from ammonium acetate on heating (v).

  1. Butanoic acid from butan-1-ol (oxidation of a 1° alcohol): CH3CH2CH2CH2OH→alk. KMnO4 / H+CH3CH2CH2COOH+H2OCH_3CH_2CH_2CH_2OH \xrightarrow{\text{alk. }KMnO_4\ /\ H^+} CH_3CH_2CH_2COOH + H_2O
  2. Butanoic acid from butanal (oxidation of an aldehyde): CH3CH2CH2CHO+[O]→K2Cr2O7/H+CH3CH2CH2COOHCH_3CH_2CH_2CHO + [O] \xrightarrow{K_2Cr_2O_7/H^+} CH_3CH_2CH_2COOH
  3. 3-Nitrobenzoic acid from 3-nitrobromobenzene (nitrile route — a Grignard is not usable in the presence of the −NO2-NO_2 group): 3-O2N-C6H4-Br→CuCN, Δ 3-O2N-C6H4-CN→H3O+, Δ 3-O2N-C6H4-COOH3{\text -}O_2N{\text -}C_6H_4{\text -}Br \xrightarrow{CuCN,\ \Delta}\ 3{\text -}O_2N{\text -}C_6H_4{\text -}CN \xrightarrow{H_3O^+,\ \Delta}\ 3{\text -}O_2N{\text -}C_6H_4{\text -}COOH
  4. Phenylethanoic acid from benzyl alcohol (raise the chain by one carbon via a nitrile): C6H5CH2OH→SOCl2C6H5CH2Cl→KCNC6H5CH2CN→H3O+C6H5CH2COOHC_6H_5CH_2OH \xrightarrow{SOCl_2} C_6H_5CH_2Cl \xrightarrow{KCN} C_6H_5CH_2CN \xrightarrow{H_3O^+} C_6H_5CH_2COOH …

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