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Identify the major product formed in the reaction given below.
Draw the major products that would form given the reaction conditions below.
What are the products of the ether cleavage reaction given below?
Consider the following compound:
When treated with HBr, this compound undergoes cleavage to form 5-bromo-5-methylhexan-1-ol. Write a plausible mechanism for this reaction.
Consider the following general scheme:
How does benzyl ether protect the 1° alcohol? What are the reagents used in the first step?
Show which bonds are broken and which bonds are formed during the following reaction. Also, indicate whether each of these bonds is a σ bond or a π bond.
How would you synthesize the given compound using organic molecules with no more than three carbons and an alcohol-protecting group?
Show the steps required to prepare the following compound from the provided starting material. Hint: A protecting group is needed.
In an enantioselective (or asymmetric) synthesis an achiral starting material is converted into mostly one enantiomer of a chiral product. For example, in the asymmetric epoxidation developed by K. Barry Sharpless, allylic alcohols are converted to epoxides with more than 90% enantiomeric excess. A typical Sharpless epoxidation uses tert-butyl hydroperoxide, titanium(IV) isopropoxide, and a dialkyl tartrate ester as the reagents, as is shown in the epoxidation of a geraniol derivative below.
(i) Identify the oxidizing agent in this reaction. What is the likely function of the other reagents?
(ii) How can the reaction give just one mostly pure enantiomer of the product?
(iii) Give the structure of the other enantiomer of the product. What reagents will you use to epoxidize the geraniol derivative to produce this other enantiomer?
The reaction shown below is an example of thiol synthesis.
The reaction consists of thiourea reacting with an alkyl chloride, followed by hydroxide-ion-promoted hydrolysis. What is the reaction's mechanism?
Starting with alkyl halide and thiol, show the preparation of the given thioester.
