How come in step 3, water doesn't attack the carbocation? Wouldn't it naturally want to immediately neutralize the carbocation instead of creating a double bond?
How come in step 3, water doesn't attack the carbocation? Wouldn't it naturally want to immediately neutralize the carbocation instead of creating a double bond?
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.SE: Something Extra
Problem 51AP
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How come in step 3, water doesn't attack the carbocation? Wouldn't it naturally want to immediately neutralize the carbocation instead of creating a double bond?
Transcribed Image Text:Step 1: Protonation of the hydroxy group (fast equilibrium).
:ÖH
H-ö-H
H,SO4
CH3-CH-CH2CH3
CH3-CH-CH2CH3
Step 2: Ionization to a carbocation (slow; rate limiting).
H-öt-H
CH3-CH-CH,CH3
→ CH;-Č-CH,CH3 +
— CH,CH,
н-ӧ—н
H
Step 3: Deprotonation to give the alkene (fast).
H
H
H
H
H,ö:
CH3
H-C-ċ-c-CH3
|| |
H H H
H
H
major product (cis and trans)
+ H;0*
H.
c=C
H
CH3
H
H
H
H,ö:
H-C-Ć-C-CH3
c=C,
H.
+ H30*
or
H
H
H H H
minor product
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