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A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.

A step in a synthesis of PGE1 (prostanglandin E1, alprostadil) is reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Alprostadil is used as temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation. Propose a mechanism for formation of This bromolactone, and account for the observed stereochemistry of each substituent on the cyclohexane ring.

Which of the following compounds is the most reactive in the nucleophilic aromatic substitution reaction with NaOH? O o-nitrochlorobenzene O m-nitrochlorobenzene O 3,5-dinitrochlorobenzene O 2,4-dinitrochlorobenzene O p-nitrochlorobenzene

Enamines can serve as enolate surrogates in reactions at the a-carbon. In the reaction sequence, the structures of the enamine addition product – the initial zwitterion and its neutral tautomer – are shown. Draw the structures of the two reactants forming these intermediates, and draw the structure of the final product, obtained via hydrolysis of the neutral intermediate. initial zwitterionic intermediate neutral intermediate tautomerization Reactants H,0 hydrolysis product Draw the two reactants. Draw the hydrolysis product. Select Draw Rings More Erase Select Draw Rings More Erase H H

Following are two possible retrosynthetic analyses for the anticholinergic drug cycri- mine. Fill in the details of each potential synthesis. O: OH + H. Cycrimine (гасemic)

Would you expect 1-methyl-1-cyclohexanol to dehydrate at a faster or slower rate than cyclohexanol? Explain your answer by referring to the mechanism of the reaction. Explain step by step in details.