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Question 65 of 69

Q.(a)

(i) How acetic acid is prepared from Grignard reagent ?
(ii) What are bio-degradable polymers ? Give an example. OR
(b) An organic Compound (A) of molecular formula C2H4OC_2H_4O reacts with Zn-Hg/Conc. HCl to give Compound (B) which reacts with HNO3HNO_3 forming Compound (C) (as major product) and Compound (D). Compound (C) reacts with conc. HCl to give Compound (E) (Table vinegar) and hydroxylamine. Identify A, B, C, D and E with suitable reactions.
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2024Subjective· 5mImportance★★★★★
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(a) A Grignard reagent adds to dry-ice CO2CO_2 and hydrolyses to a carboxylic acid; biodegradable polymers like PHBV are broken down by microbes. (b) Tracing the clue chain (Clemmensen reduction, then nitration, then nitroalkane hydrolysis to acid + hydroxylamine) identifies A-E as acetaldehyde, ethane, nitroethane, nitromethane, and acetic acid.

(a)(i) Acetic acid from a Grignard reagent: Methylmagnesium iodide, CH3MgICH_3MgI, is added to solid carbon dioxide (dry ice); the nucleophilic methyl carbanion of the Grignard reagent adds to the electrophilic carbon of CO2CO_2, forming a magnesium carboxylate salt, which on acidic hydrolysis (dilute acid, H3O+H_3O^+) liberates the free carboxylic acid: CH3MgI+CO2→CH3COOMgI→H3O+CH3COOH (acetic acid)+Mg(OH)ICH_3MgI + CO_2 \rightarrow CH_3COOMgI \xrightarrow{H_3O^+} CH_3COOH\ (\text{acetic acid}) + Mg(OH)I

(a)(ii) Biodegradable polymers: These are polymers that can be broken down (degraded) by the action of microorganisms (bacteria, fungi) into simple, non-toxic products such as CO2CO_2, water, and biomass, unlike conventional plastics which persist in the environment for very long periods. Example: PHBV (poly-β\beta-hydroxybutyrate-co-β\beta-hydroxyvalerate), a copolymer of 3-hydroxybutanoic acid and 3-hydroxypentanoic (valeric) acid, used in specialty packaging and controlled drug-release/orthopaedic applications; another example is nylon-2-nylon-6.

OR (b) Identifying A-E:

Compound A (C2H4OC_2H_4O) reacted with ZnZn-HgHg/conc.HCl (Clemmensen reduction, which reduces a carbonyl group fully to −CH2−-CH_2-) — this points to A being an aldehyde/ketone that is reduced to an alkane, so A=A= acetaldehyde, CH3CHOCH_3CHO. Clemmensen reduction converts it to B=B= ethane, CH3CH3CH_3CH_3: CH3CHO→conc. HClZn(Hg)CH3CH3CH_3CHO \xrightarrow[\text{conc. HCl}]{Zn(Hg)} CH_3CH_3

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