Ethers containing the 1,1-dimethylethyl (tert-butyl) group are readily cleaved with dilute, strong acid. Draw curved arrows to suggest a plausible mechanism for this process. H₂C-CH₂ CH3 CH-O-C- -CH3 H₂C-CH₂ CH3 H₂C-CH₂ H3C Do not delete any pre-drawn bonds, charges, or lone pairs. If you accidentally make a mistake, remove the last change by using the undo button on the lower left or revert the drawing palette to the original state by selecting the More menu, then select Reset Drawing. H₂C Step 1: Draw a curved arrow. H₂C CF3CO₂H, H₂O CH₂ CH₂ H₂C-CH₂ CH₂ H₂C CH-OH H + H HC с Ofe Ote HC 0 с c c - c H₂ H₂ + H₂C H3C C=CH₂ Step 2: Draw a curved arrow. CH₂ CH₂ CH₂

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
Section: Chapter Questions
Problem 26E
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Step 3: Draw curved arrows.
H.C
с-
н
C
н
HC - ОН
Н.С
н с
H
CH₂
|·
Н
H2C — CH2
H2C
H2C
H3C
H3C
+
CH-OH
-CH₂
C=CH2
H30+
Transcribed Image Text:Step 3: Draw curved arrows. H.C с- н C н HC - ОН Н.С н с H CH₂ |· Н H2C — CH2 H2C H2C H3C H3C + CH-OH -CH₂ C=CH2 H30+
Ethers containing the 1,1-dimethylethyl (tert-butyl) group are readily cleaved with dilute, strong acid. Draw curved arrows to
suggest a plausible mechanism for this process.
H₂C-CH₂
CH3
H₂C
CH-O
Step 1: Draw a curved arrow.
H₂C
H₂
H₂
c c
H₂
-CH3
HC
H3C
H₂C-CH₂
CH3
Do not delete any pre-drawn bonds, charges, or lone pairs. If you accidentally make a mistake, remove the last change by using
the undo button on the lower left or revert the drawing palette to the original state by selecting the More menu, then select
Reset Drawing.
H +
CF3CO₂H,
H₂O
H₂C-CH₂
CH₂
CH₂
H₂C
H₂C
Ofe-046
CH₂
I
CH-OH
H₂C-CH₂
H₂
Step 2: Draw a curved arrow.
H₂
с
+
с
H3C
H₂
C=CH₂
HC
H
C
CH3
CH₂
CH₂
↑
Transcribed Image Text:Ethers containing the 1,1-dimethylethyl (tert-butyl) group are readily cleaved with dilute, strong acid. Draw curved arrows to suggest a plausible mechanism for this process. H₂C-CH₂ CH3 H₂C CH-O Step 1: Draw a curved arrow. H₂C H₂ H₂ c c H₂ -CH3 HC H3C H₂C-CH₂ CH3 Do not delete any pre-drawn bonds, charges, or lone pairs. If you accidentally make a mistake, remove the last change by using the undo button on the lower left or revert the drawing palette to the original state by selecting the More menu, then select Reset Drawing. H + CF3CO₂H, H₂O H₂C-CH₂ CH₂ CH₂ H₂C H₂C Ofe-046 CH₂ I CH-OH H₂C-CH₂ H₂ Step 2: Draw a curved arrow. H₂ с + с H3C H₂ C=CH₂ HC H C CH3 CH₂ CH₂ ↑
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