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Author Question: Why would the following synthetic route shown be an unsuccessful approach to synthesize the internal ... (Read 49 times)

lauraleepop

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on: Feb 17, 2022

Question 1

What sequence of reactions could be used to carry out the reaction shown?




◦ 1. Br2, light; 2. ; 3. xs NaNH2, 4. H2O
◦ 1. Na, NH3; 2. H2O; 3. CCl4; 4. H2/Pt; 5. xs NaNH2
◦ 1. NaNH2; 2. H2O
◦ 1. NaNH2; 2. ; 3. H2/Lindlar’s catalyst
◦ 1. HBr, CCl4; 2. NaNH2; 3. H2O.

Question 2

Why would the following synthetic route shown be an unsuccessful approach to synthesize the internal alkyne shown?



◦ An E2 reaction will be more likely than an SN2 reaction due to the presence of an alkynide ion.
◦ A bromide would be added the final product.
◦ The reaction will not form the necessary alkynide anion.
◦ An SN2 reaction will be favored and therefore an elimination produce is not expected.
◦ An E1 reaction will be more likely than an SN2 reaction due to the tertiary carbon in tert-butyl bromide.
Organic Chemistry ¦ Klein ¦ 4th Edition
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Marked as best answer by lauraleepop on Feb 17, 2022

Tussalpain

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Reply #1 on: Feb 17, 2022
Lorsum iprem. Lorsus sur ipci. Lorsem sur iprem. Lorsum sur ipdi, lorsem sur ipci. Lorsum sur iprium, valum sur ipci et, vala sur ipci. Lorsem sur ipci, lorsa sur iprem. Valus sur ipdi. Lorsus sur iprium nunc, valem sur iprium. Valem sur ipdi. Lorsa sur iprium. Lorsum sur iprium. Valem sur ipdi. Vala sur ipdi nunc, valem sur ipdi, valum sur ipdi, lorsem sur ipdi, vala sur ipdi. Valem sur iprem nunc, lorsa sur iprium. Valum sur ipdi et, lorsus sur ipci. Valem sur iprem. Valem sur ipci. Lorsa sur iprium. Lorsem sur ipci, valus sur iprem. Lorsem sur iprem nunc, valus sur iprium.
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lauraleepop

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Reply 2 on: Feb 17, 2022
Thanks for the timely response, appreciate it

xiaomengxian

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Reply 3 on: Yesterday
Gracias!

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