Chapter 11: Q52P (page 589)
Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.
Short Answer
Step by step solution
About alcohol
The compound that bears one or more hydroxide groups (OH) is called alcohol. The alcohols have very large applications in organic synthesis. It has wide applications in perfume and cleaning agents.
About the reaction
Compound A is butan-2-ol. When it is treated with PB3, it forms 2-bromobutane. So the compound C is 2-bromobutane. When it is treated with magnesium metal in the ether it forms sec-butylmagnesium bromide. So, compound D is sec-butylmagnesium bromide.
About the reaction
When butan-2-ol is treated with NaOCl/HOAc it gives butan-2-one. So, compound B is butan-2-one. When sec-butylmagnesium and butan-2-one react together, there will be the formation of magnesium 3,4-dimethylhexan-3-olate bromide. So, compound E is magnesium 3,4-dimethylhexan-3-olate bromide. When it is acidified, 3,4-dimethylhexan-3-ol is formed. So, the final compound is 3,4-dimethylhexan-3-ol. The reaction is shown below.
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