Propose a plausible mechanism for the following transformation. HO 1) H-CEC: Na 2) H3Oʻ

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 47AP
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Propose a plausible mechanism for the following transformation.
но
1) H-CEC: Na
2) H;0*
13.38c
Correct. The acetylide ion functions as a nucleophile and attacks the neutral epoxide ring, and protonation of the
resulting alkoxide occurs with aqueous workup.
Identify the most likely sequence of steps in the mechanism:
Step 1:
nucleophilic attack
Step 2:
protonate
Step 3:
none (only 2 steps)
eTextbook and Media
Transcribed Image Text:Propose a plausible mechanism for the following transformation. но 1) H-CEC: Na 2) H;0* 13.38c Correct. The acetylide ion functions as a nucleophile and attacks the neutral epoxide ring, and protonation of the resulting alkoxide occurs with aqueous workup. Identify the most likely sequence of steps in the mechanism: Step 1: nucleophilic attack Step 2: protonate Step 3: none (only 2 steps) eTextbook and Media
13.38c1
Add curved arrow(s) to draw step 1 of the mechanism. Modify the given drawing of the product as needed to show the
intermediate that is formed in this step (do not draw the counterion).
H;C-
H,C-
+
: E CH
Edit Drawing
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Transcribed Image Text:13.38c1 Add curved arrow(s) to draw step 1 of the mechanism. Modify the given drawing of the product as needed to show the intermediate that is formed in this step (do not draw the counterion). H;C- H,C- + : E CH Edit Drawing Save for Later Attempts: 0 of 3 used Submit Answer
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