Review Acid-Catalyzed Dehydration of an Alcohol

Dehydration results from E1 elimination of the protonated alcohol Step I Protonation converts the hydroxyl group to a good leaving group. [Pg.480]

Let s review the utility of dehydration and give guidelines for predicting the products [Pg.482]

Dehydration usually goes by the E1 mechanism. Rearrangements may occur to form more stable carbocations. [Pg.482]

Dehydration works best with tertiary alcohols and almost as well with secondary alcohols. Rearrangements and poor yields are common with primary alcohols. [Pg.482]

(Zaitsev s rule) If two or more alkenes might be formed by deprotonation of the carbocation, the most highly substituted alkene usually predominates. [Pg.482]

Mechanism 11-4 (Review) Acid-Catalyzed Dehydration of an Alcohol 487... [Pg.11]

Hydride Reduction of a Carbonyl Group 454 Reaction of a Tertiary Alcohol with HBr(S[ 1) 480 Reaction of a Primary Alcohol with HBr (SN2) 480 Reaction of Alcohols with PBr3 485 (Review) Acid-Catalyzed Dehydration of an Alcohol 487 The Pinacol Rearrangement 495 Cleavage of an Ether by HBr or HI 639 Acid-Catalyzed Opening of Epoxides in Water 649 Acid-Catalyzed Opening of an Epoxide in an Alcohol Solution 650... [Pg.1293]

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