Textbook Question
Show how each of the following compounds can be prepared from the given starting material. In each case, you will need to use a protecting group.
a.
b.
12. Alcohols, Ethers, Epoxides and Thiols
Silyl Ether Protecting Groups
Multiple Choice
Which of the follosing is the best synthesis of the given molecule?
A
B
C
D
Verified step by step guidance1
Identify the target molecule: The target molecule is a secondary alcohol with a phenyl group and a chloro group on adjacent carbon atoms.
Analyze the first synthesis route: The first image shows a reaction sequence starting with a triethylsilyl chloride (Et3SiCl) protection of the alcohol, followed by HCl treatment, and then deprotection with Bu4NF. This sequence is likely to protect the alcohol, introduce the chloro group, and then deprotect the alcohol.
Analyze the second synthesis route: The second image shows a similar sequence but starts with HCl treatment, which might lead to the formation of a carbocation and subsequent rearrangement or substitution reactions.
Analyze the third synthesis route: The third image shows a simple HCl treatment, which might lead to the formation of a chloro group via a substitution reaction, but lacks the protection step for the alcohol.
Analyze the fourth synthesis route: The fourth image shows a tosyl chloride (TsCl) protection of the alcohol, followed by HCl treatment, and then deprotection with Bu4NF. This sequence is similar to the first but uses a different protecting group, which might affect the reaction conditions and outcomes.
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