Which of the following best explains why the synthetic route shown below would be unsuccessful? 1) CH;CH,Br HCEC: CH;CH,C=CC(CH3)a 2) NANH2 3) (CH3)3CBr O Reaction with sodium amide will result in formation of a primary alkyne O The alkynide anion formed by reaction with sodium amide will facilitate an E2 (rather than SN2) reaction with t-butyl bromide O The alkynide anion is not a strong enough nucleophile to react with 1-bromopropane in step 1 Sodium amide is not a strong enough base to deprotonate the terminal alkyne in step 2 O Both substitution reactions will occur on the same end of the alkyne, making a product different than the one shown

Which of the following best explains why the synthetic route shown below would be unsuccessful? 1) CH;CH,Br HCEC: CH;CH,C=CC(CH3)a 2) NANH2 3) (CH3)3CBr O Reaction with sodium amide will result in formation of a primary alkyne O The alkynide anion formed by reaction with sodium amide will facilitate an E2 (rather than SN2) reaction with t-butyl bromide O The alkynide anion is not a strong enough nucleophile to react with 1-bromopropane in step 1 Sodium amide is not a strong enough base to deprotonate the terminal alkyne in step 2 O Both substitution reactions will occur on the same end of the alkyne, making a product different than the one shown

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter11: Ethers, Epoxides, And Sulfides

Section11.9: Reactions Of Epoxides

Problem DQ

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