A compound (A) (which gives haloform reaction), on reduction with zinc amalgam and conc.HCl gives (B). (B) is also obtained by treating \(1,1,2,2\) - tetrachlorobutane with zinc dust. The compound (A) is (a) C#CC(C)O (b) C=C(C)C=O (c) C=CC(C)O (d) C#CC=O

Short Answer

Expert verified
Question: Identify the compound (A) that gives a haloform reaction and on reduction with zinc amalgam and conc. HCl gives (B), which is also obtained by treating 1,1,2,2-tetrachlorobutane with zinc dust. Choose the correct compound (A) out of the given options: (a) \(\mathrm{CH_3C\equivCCH_2OH}\), (b) \(\mathrm{CH_3CH=C(CH_3)CHO}\), (c) \(\mathrm{CH_3CH=C(CH_3)CH_2OH}\), (d) \(\mathrm{CH_3C\equiv CCHO}\). Answer: Compound (A) is (b) \(\mathrm{CH_3CH=C(CH_3)CHO}\).

Step by step solution

01

Identify the functional group in each given compound and determine if they can give haloform reaction or not.

(a) \(\mathrm{CH_3C\equivCCH_2OH}\): This compound has a terminal alkyne functional group and a primary alcohol group. Alcohols (except for methyl ketones) do not give haloform reactions. So, option (a) can be ruled out. (b) \(\mathrm{CH_3CH=C(CH_3)CHO}\): This compound has an aldehyde functional group and an alkene functional group. Aldehydes with at least one alpha hydrogen can give haloform reactions. In this case, there's one alpha hydrogen present. So, option (b) is a candidate for compound (A). (c) \(\mathrm{CH_3CH=C(CH_3)CH_2OH}\): This compound has an alkene functional group and a primary alcohol functional group, which does not give haloform reactions. So, option (c) can be ruled out. (d) \(\mathrm{CH_3C\equivCCHO}\): This compound has a terminal alkyne functional group and an aldehyde functional group. Like we discussed earlier, aldehydes with one alpha hydrogen can give haloform reactions, which is true for this compound as well. Therefore, option (d) is also a candidate for compound (A). Now, we have two candidates for compound (A): option (b) and option (d).
02

Find the product (B) obtained by reducing each compound with zinc amalgam and conc. HCl.

(b) Reducing \(\mathrm{CH_3CH=C(CH_3)CHO}\) with zinc amalgam and conc. HCl will reduce the aldehyde group to a primary alcohol: \(\mathrm{CH_3CH=C(CH_3)CH_2OH}\). (d) Reducing \(\mathrm{CH_3C\equiv CCHO}\) with zinc amalgam and conc. HCl will reduce the aldehyde group to a primary alcohol: \(\mathrm{CH_3C\equiv CCH_2OH}\).
03

Compare the obtained products with the product formed by treating 1,1,2,2-tetrachlorobutane with zinc dust.

Treating 1,1,2,2-tetrachlorobutane with zinc dust will reduce two carbon-chlorine bonds to form a double bond: \(\mathrm{CCl_2CHCHCl_2}\) \(\xrightarrow{\mathrm{Zn\ \mathrm{dust}}}\) \(\mathrm{CH_2=CH-CHCl_2}\). Comparing this product with the products obtained by reducing compounds (b) and (d), we see a match between this product and the one obtained by reducing compound (b). Therefore, compound (A) is: (b) \(\mathrm{CH_3CH=C(CH_3)CHO}\).

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