Chemistry(A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular formula C4H8O. Isomers (A) and (C) give positive Tollen’s test whereas isomer (B) does not give Tollen’s test but gives positive iodoform test. Isomers (A) and (B) on reduction with Zn(Hg)/conc. HCI give the same product (D).

(A), (B) and (C) are three non-cyclic functional isomers of a carbonyl compound with molecular formula C4H8O. Isomers (A) and (C) give positive Tollen's test whereas isomer (B) does not give Tollen's test but gives positive iodoform test. Isomers (A) and (B) on reduction with Zn(Hg)/conc. HCI give the same product (D).

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    Solution:

    Part (a): Structure of A, B, C, and D Analyzing the given tests:
    • Tollen’s test is given by aldehydes and ketones do not give Tollen's test.
    • The iodoform test is given by compounds that have a methyl group attached to a carbonyl carbon.
    • The reagent Zn(Hg)/HClZn(Hg)/HClZn(Hg)/HCl is Clemmensen’s reagent and reduces carbonyl carbon into methylene.

    Identifying the compound B:

    • Compound B does not give Tollen's test but gives the iodoform test.
    • So, compound B is a methyl ketone.

    Identifying the compound A, C, and D:

    • Compound A gives the Tollen's test. So, it is an aldehyde and it also gave the same product on reaction with Clemmenson reagent as given by compound B.
    • The compounds B and A gave the same product D on reacting with Clemmensen reagent.
    • Compound C is also an aldehyde.

    Part b: Which is less reactive towards HCNHCNHCN

    • HCN addition reaction to a carbonyl compound is a bimolecular reaction.
    • The rate of bimolecular reaction depends upon the steric hindrance.
    • So, the compound containing large substituents is less reactive towards HCN addition reaction.
    • Hence, ketones are less reactive as compared to aldehyde.
    • So, compound B is least reactive towards HCN addition reaction.
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