Exam 18: Ethers and Epoxides;thiols and Sulfides

Name the compound shown below.Atoms other than carbon and hydrogen are labeled.

Exhibit 18-1 Consider the reaction below to answer the following question(s). -Refer to Exhibit 18-1.Write the complete stepwise mechanism for the reaction.Show all intermediate structures and all electron flow with arrows.

What is the product formed upon treatment of the following substance with hydrogen peroxide at room temperature,followed by treatment with a peroxyacid? Atoms other than carbon and hydrogen are labeled.

Name the following compound.Atoms other than carbon and hydrogen are labeled.

Draw: allyl benzyl ether

Name:

Propose a synthesis for the following compound using benzene or toluene and any other reagents necessary.Show all major intermediate compounds that would probably be isolated during the course of your synthesis.

Complete the synthetic sequence below by drawing the structures of the reaction in the boxes provided.

Exhibit 18-2 Consider the data below to answer the following question(s). Acetals are a special class of ethers which have two ether linkages at a single carbon.Tetrahydropyranyl ethers are acetals that are easily cleaved with mild aqueous acids at room temperature to yield alcohols. -Refer to Exhibit 18-2.This ether cleavage occurs so easily under such mild conditions because the carbocation intermediate in step two is very stable.Explain why this carbocation is stabilized.

Draw: tetrahydrofuran

Diphenyl ether is inert to cleavage by HI or HBr.Explain.

Exhibit 18-3 Consider the data below to answer the following question(s). ​ Epoxides are synthesized industrially in one step by silver oxide air oxidation of ethylene and on a laboratory scale in one step by treating an alkene with m-chloroperoxybenzoic acid.An alternative two-step process converts alkenes to halohydrins,which are converted by treatment with base to epoxides. ​ -Refer to Exhibit 18-3.Show electron flow with arrows on the structures provided below for each step in the above transformation.

Exhibit 18-1 Consider the reaction below to answer the following question(s). -Refer to Exhibit 18-1.Mechanistically,the Williamson ether synthesis outlined above is: