The reaction of sec-butylmagnesium bromide with formaldehyde followed by hydrolysis yields?
2,2-dimethyl-1-pentanol
2-butanol
2-methyl-1-butanol
2-pentanol
2,2-dimethyl-1-propanol
The magnesium bromide group on the #2 carbon of the butyl chain is replaced by a -CH2OH. The longest chain on this product has 4 carbon atoms.
To determine the product of the reaction of sec-butylmagnesium bromide with formaldehyde followed by hydrolysis, we need to consider the reaction mechanism and the structures of the reactant molecules.
First, let's understand the reaction mechanism:
1. Formation of Grignard Reagent:
Sec-butylmagnesium bromide, CH3CHBrCH(CH3)CH2MgBr, reacts with formaldehyde, HCHO, to form a Grignard reagent intermediate. The magnesium atom in the Grignard reagent is bonded to the carbon atom carrying the sec-butyl group.
2. Addition of Grignard Reagent to Formaldehyde:
The nucleophilic Grignard reagent attacks the electrophilic carbon atom of formaldehyde. This results in the formation of a carbon-carbon bond.
3. Hydrolysis:
After the addition of the Grignard reagent to formaldehyde, hydrolysis is carried out, where water is added to break apart the reaction intermediates and create the final product.
Now, let's determine the product:
Sec-butylmagnesium bromide reacts with formaldehyde to form a Grignard reagent intermediate. The Grignard reagent adds to the electrophilic carbon atom of formaldehyde, resulting in the formation of a new carbon-carbon bond.
The final product obtained after hydrolysis will depend on the position of the carbon atom where the Grignard reagent added. In this case, the Grignard reagent added to the carbonyl carbon atom of formaldehyde. This leads to the formation of a secondary alcohol.
Considering the given options, the product 2-methyl-1-butanol (option C) is the correct answer.
To determine the product, an understanding of organic chemistry, reaction mechanisms, and the ability to analyze the structures of the reactants and products is necessary. This involves knowledge of functional groups, reactivity, and reaction types.