2 (167)

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d) The reaction of primary alcohols with HCI requires the presence of the Lewis acid ZnCl₂. 10.41 a) The acetylide anion produced in the first step is a strong base, so the second step favors E2 elimination. b) Multiple alkylation competes, giving a low yield of the desired primary amine. c) The ether is formed in low yield because the secondary alkyl chloride and the strong base favor E2 elimination. d) Nucleophilic substitution on a benzene ring does not occur. e) This reaction follows the SN1 mechanism, so the product is a mixture of stereoisomers. f) This is an E1 elimination reaction. The initially formed secondary carbocation can rearrange to form a more stable tertiary carbocation. Therefore, this reaction produces a mixture of products in which the product shown is only a minor component. 10.42 a) CH₃ CH₃ CH₃ + H₃ C Br + H₃ C C CH₃ CH₃ CH₃ CH₃ H B CH₃ H₃C C CH₃ CH₃ b) H O H-O-S-OH H O H + CH₃CH₂ OH₂ CH₃CH₂ CH₂CH₃ + CH₃CH₂ H + CH₃CH₂OCH₂CH₃ + 163