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Hydrocarbon (A) C(6)H(10), on treatment ...

Hydrocarbon (A) `C_(6)H_(10)`, on treatment with `H_(2)//Ni, H_(2)`/ Lindlar's catalylst and Na/liquid `NH_(3)` forms three different reduction products (B), ( C) and (D) respectively. (A) does not form any salt with ammoniacal `AgNO_(3)` solution, but forms a salt (E) on heating with `NaNH_(2)` in an inert solvent. Compound (E) reacts with `CH_(3)I` to give (F). Compound (D) on oxidative ozonolysis gives n-butanoic acid along with other product.
Give structures of (A) to (F) with proper reasoning.

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To solve the problem step-by-step, we will identify the structures of compounds (A) to (F) based on the information provided. ### Step 1: Identify Compound (A) Given that compound (A) has the molecular formula \(C_6H_{10}\), it can be classified as an alkyne since it follows the formula \(C_nH_{2n-2}\). To satisfy the condition that (A) does not form a salt with ammoniacal \(AgNO_3\), it must be a non-terminal alkyne. A suitable structure for (A) is: \[ \text{(A): } CH_3CH_2CH_2C \equiv C CH_3 \] This is 2-heptyne, a non-terminal alkyne. ### Step 2: Identify Compound (B) When compound (A) is treated with \(H_2\) in the presence of nickel (\(Ni\)), it undergoes complete hydrogenation to form an alkane: \[ \text{(B): } CH_3CH_2CH_2CH_2CH_2CH_3 \] This is hexane. ### Step 3: Identify Compound (C) When compound (A) is treated with \(H_2\) using Lindlar's catalyst, it undergoes partial hydrogenation to form a cis-alkene: \[ \text{(C): } CH_3CH_2CH_2C=CH_2 \] This is cis-2-hexene. ### Step 4: Identify Compound (D) When compound (A) is treated with sodium in liquid ammonia, it undergoes Birch reduction, resulting in a trans-alkene: \[ \text{(D): } CH_3CH_2CH_2C=CHCH_3 \] This is trans-2-hexene. ### Step 5: Identify Compound (E) Compound (A) does not form a salt with ammoniacal \(AgNO_3\) but forms a salt (E) when heated with \(NaNH_2\) in an inert solvent: \[ \text{(E): } CH_3CH_2CH_2C \equiv CNa \] This is the sodium salt of the alkyne. ### Step 6: Identify Compound (F) When compound (E) reacts with \(CH_3I\) (methyl iodide), it forms: \[ \text{(F): } CH_3CH_2CH_2C \equiv CH_3 \] This is 1-heptyne. ### Step 7: Additional Information for Compound (D) Compound (D) on oxidative ozonolysis gives n-butanoic acid and another product: The ozonolysis of trans-2-hexene (D) results in: \[ \text{Products: } CH_3CH_2CH_2COOH \text{ (n-butanoic acid) and } CH_3COOH \text{ (acetic acid)} \] ### Summary of Structures: - **(A)**: \( CH_3CH_2CH_2C \equiv C CH_3 \) (2-heptyne) - **(B)**: \( CH_3CH_2CH_2CH_2CH_2CH_3 \) (hexane) - **(C)**: \( CH_3CH_2CH_2C=CH_2 \) (cis-2-hexene) - **(D)**: \( CH_3CH_2CH_2C=CHCH_3 \) (trans-2-hexene) - **(E)**: \( CH_3CH_2CH_2C \equiv CNa \) (sodium salt of 2-heptyne) - **(F)**: \( CH_3CH_2CH_2C \equiv CH_3 \) (1-heptyne)
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