Which of the following respectively form primary, secondary and tertiary alcohols by reaction with Grignard reagent followed by hydrolysis? (a) Formaldehyde, acetone, acetaldehyde (b) Formaldehyde, acetaldehyde, acetone (c) Acetaldehyde, acetone, formaldehyde (d) Acetone, acetaldehyde, formaldehyde

When a Grignard reagent reacts with a carbonyl compound, it forms an alkoxide which, upon hydrolysis, forms the corresponding alcohol. The general reaction can be represented as: R-MgX + R'CHO -> R-(CH2O)-R' -> [H3O+] -> R-CH2-R' + MgX(OH) Where R and R' are alkyl groups and X is a halogen.

We can determine the type of alcohol formed by counting the number of alkyl (R) groups attached to the carbon that holds the hydroxyl group (OH). If there is 1 R group, it is a primary alcohol; 2 R groups, secondary alcohol; and 3 R groups, tertiary alcohol.

We will now examine each set of carbonyl compounds provided in the options and determine which type of alcohol they would form upon reaction with the Grignard reagent. (a) Formaldehyde, acetone, acetaldehyde Formaldehyde (H-CH=O) would form primary alcohol (R-CH2OH) because it has no R groups attached. Acetone ((CH3)2C=O) would form tertiary alcohol (R-C(CH3)2OH) because it has 2 R groups attached. Acetaldehyde (CH3-CH=O) would form secondary alcohol (R-CH(CH3)OH) because it has 1 R group attached. (b) Formaldehyde, acetaldehyde, acetone Formaldehyde (H-CH=O) would form primary alcohol (R-CH2OH) because it has no R groups attached. Acetaldehyde (CH3-CH=O) would form secondary alcohol (R-CH(CH3)OH) because it has 1 R group attached. Acetone ((CH3)2C=O) would form tertiary alcohol (R-C(CH3)2OH) because it has 2 R groups attached. (c) Acetaldehyde, acetone, formaldehyde Acetaldehyde (CH3-CH=O) would form secondary alcohol (R-CH(CH3)OH) because it has 1 R group attached. Acetone ((CH3)2C=O) would form tertiary alcohol (R-C(CH3)2OH) because it has 2 R groups attached. Formaldehyde (H-CH=O) would form primary alcohol (R-CH2OH) because it has no R groups attached. (d) Acetone, acetaldehyde, formaldehyde Acetone ((CH3)2C=O) would form tertiary alcohol (R-C(CH3)2OH) because it has 2 R groups attached. Acetaldehyde (CH3-CH=O) would form secondary alcohol (R-CH(CH3)OH) because it has 1 R group attached. Formaldehyde (H-CH=O) would form primary alcohol (R-CH2OH) because it has no R groups attached.

The correct order of carbonyl compounds that form primary, secondary, and tertiary alcohols upon reaction with Grignard reagent followed by hydrolysis is formaldehyde, acetaldehyde, and acetone as given in option (b).