A compound (X) of molecular formula `C_(3)H_(6)O` forms bisulphate complex, gives iodoform test but does not reduce Tollens reagent. (X) on reaction with `CH_(3)MgBr//H_(3)O^(+)` gives a compound (Y) that cannot

Options

A. give red colour with Cerium Ammonium Nitrate (CAN)
B. give white turbidity immediately with Lucas reagent
C. give iodoform test
D. be dehydrated to alkene on reaction with heated Cu

Answer

To solve the problem, we need to analyze the information given about the compound (X) with the molecular formula \( C_3H_6O \).

### Step 1: Identify the structure of compound (X)
The molecular formula \( C_3H_6O \) suggests that (X) could be either an aldehyde or a ketone.

- Aldehyde structure: \( CH_3CH_2CHO \)
- Ketone structure: \( CH_3C(=O)CH_3 \)

### Step 2: Analyze the chemical tests
1. **Iodoform Test**: This test is positive for methyl ketones (compounds with the structure \( RCOCH_3 \)). Therefore, if (X) gives a positive iodoform test, it must be a ketone.
2. **Tollens' Reagent**: Aldehydes reduce Tollens' reagent, while ketones do not. Since (X) does not reduce Tollens' reagent, it cannot be an aldehyde.

### Conclusion about (X)
Since (X) gives a positive iodoform test and does not reduce Tollens' reagent, (X) must be the ketone \( CH_3C(=O)CH_3 \) (acetone).

### Step 3: Reaction with Grignard Reagent
When (X) reacts with \( CH_3MgBr \) followed by hydrolysis with \( H_3O^+ \), it produces a tertiary alcohol (Y). The reaction can be outlined as follows:

1. The Grignard reagent \( CH_3MgBr \) attacks the carbonyl carbon of the ketone, forming an alkoxide intermediate.
2. Upon hydrolysis, this intermediate is converted to the corresponding tertiary alcohol.

The structure of (Y) will be:
\[ Y = CH_3C(OH)(CH_3)CH_3 \] (tert-butyl alcohol).

### Step 4: Analyze the properties of compound (Y)
Now we need to evaluate the options given in the question about compound (Y):

1. **Red color with cerium ammonium nitrate**: True, as tertiary alcohols can form colored complexes with cerium salts.
2. **White turbidity with Lucas reagent**: True, as tertiary alcohols react quickly with Lucas reagent to form alkyl chlorides.
3. **Gives iodoform test**: False, as iodoform test is not given by tertiary alcohols.
4. **Dehydrated to alkene on reaction with heated copper**: True, as tertiary alcohols can dehydrate to form alkenes under heating.

### Final Answer
The compound (Y) cannot give the iodoform test.