Chapter 11: Q31P (page 573)
Show the alcohol and the acid chloride that combine to make the following esters.
(a) 
(b) 
(c) 
(d) 
Short Answer
(a) 
(b) 
(c) 
(d) 
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Chapter 11: Q31P (page 573)
Show the alcohol and the acid chloride that combine to make the following esters.
(a) 
(b) 
(c) 
(d) 
(a) 
(b) 
(c) 
(d) 
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When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.
(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.
Use resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa= -2.6) is a much stronger acid than acetic acid (CH3COOH,pKa =4.8)
Under acid catalysis, tetrahydrofurfuryl alcohol reacts to give surprisingly good yields of dihydropyran. Propose a mechanism to explain this useful synthesis.

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation usingand pyridine, followed by elimination using KOC(CH3)3as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.
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