Question

Identify the starting compound from the following data: \[ C_6H_{14}O(X) \text{ on reaction with HI yields a haloalkane (A) and an alcohol (B).} \] Compound (A) on reaction with aqueous NaOH gives an alcohol (C). Compounds (B) and (C) on reaction with CrO\(_3\) in anhydrous medium yields Butanone and Ethanal respectively.

• A. 2-Methoxypentane
• B. 2-Ethyxbutane
• C. Hexan-1-ol
• D. Hexan-2-ol

Hint:

When analyzing organic reactions, it's important to consider the typical products of reactions with reagents like NaOH and CrO\(_3\), as these can help you deduce the structure of the starting compoun(D)

Answer 1

The Correct Option is B

We are asked to identify the starting compound based on the given reactions and products. Let’s break down the data step by step: Step 1: Reaction with HI We are told that \( C_6H_{14}O(X) \) reacts with HI and produces a haloalkane (A) and an alcohol (B). This suggests that \( C_6H_{14}O(X) \) is an ether, because ethers react with HI to yield alcohols and haloalkanes. Step 2: Compound (A) with aqueous NaOH Next, compound (A) is treated with aqueous NaOH and gives an alcohol (C). This indicates that compound (A) is a haloalkane and undergoes a nucleophilic substitution reaction, typical of alkyl halides. Step 3: Compound (B) and (C) with CrO\(_3\) Finally, compounds (B) and (C) are reacted with CrO\(_3\) in anhydrous medium, yielding Butanone and Ethanal respectively. This suggests that compound (B) is a secondary alcohol (since it gives butanone), and compound (C) is a primary alcohol (since it gives ethanal upon oxidation). Step 4: Conclusion From this information, the compound \( C_6H_{14}O(X) \) must be 2-Ethoxybutane, as this fits the pattern of reactions described above. Thus, the correct answer is \( \boxed{2} \) 2-Ethyxbutane.