Identify Compound A and Compound B, which are isomers of C4H10O. Compound A reacts with H2SO4 to form Compound B and H2O. Compound A does not react with Fehling's reagent. Then, list all isomers of C4

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Part A: Identify Compound A and Compound B

Compound A has the molecular formula C4H10O. It reacts with H2SO4 to form compound B (C4H8) and H2O. This is a dehydration reaction, indicating that A is an alcohol and B is an alkene. Compound A also reacts with sodium, which is characteristic of alcohols.

Given the formula C4H10O, the possible alcohol isomers are:

1. Butan-1-ol (primary alcohol)
2. Butan-2-ol (secondary alcohol)
3. 2-Methylpropan-1-ol (primary alcohol)
4. 2-Methylpropan-2-ol (tertiary alcohol)

The problem states that Compound A has no effect on Fehling's reagent. Fehling's reagent tests for aldehydes. Primary alcohols can be oxidized to aldehydes, which would react with Fehling's. Secondary alcohols oxidize to ketones, which do not react with Fehling's. Tertiary alcohols are resistant to oxidation under mild conditions and thus would not react with Fehling's. The most definitive "no effect" for an alcohol is a tertiary alcohol.

Therefore, Compound A is a tertiary alcohol.

$$\text{Compound A: } \boxed{\text{2-Methylpropan-2-ol}}$$

The dehydration of 2-Methylpropan-2-ol yields 2-methylpropene.

$$\text{Compound B: } \boxed{\text{2-Methylpropene}}$$

Part B: Write name and structural formulae of all possible isomers of C4H10O that can be oxidized to give a product that would be detected by Fehling's reagent.

Fehling's reagent detects aldehydes. Therefore, we are looking for primary alcohol isomers of C4H10O, as primary alcohols can be oxidized to aldehydes.

1. Butan-1-ol Structural formula: $\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OH}$ Oxidation product: Butanal (an aldehyde)

2. 2-Methylpropan-1-ol Structural formula: $(\text{CH}_3)_2\text{CHCH}_2\text{OH}$ Oxidation product: 2-Methylpropanal (an aldehyde)

Part C: Name any reagent that can be used to distinguish between butan-1-ol and butan-2-ol and state what would be observed with the reagent.

Butan-1-ol is a primary alcohol, and butan-2-ol is a secondary alcohol.

• Reagent: Lucas reagent (concentrated hydrochloric acid, HCl, and anhydrous zinc chloride, ZnCl2).

• Observation with Butan-1-ol (primary alcohol): No visible reaction (no cloudiness) at room temperature, or a very slow reaction.

• Observation with Butan-2-ol (secondary alcohol): The solution will turn cloudy within 5-20 minutes as 2-chlorobutane is formed.