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Organic Chemistry 6 Edition: Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination
Organic Chemistry 6 Edition: Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination
Organic Chemistry 6 Edition: Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination
Elimination Reactions
of Alkyl Halides
Competition Between
Substitution and
Elimination
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In addition to substitution, an alkyl halide can undergo an
elimination reaction
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The E2 Reaction
• reaction and mechanism
• kinetics
• Stereochemistry
• regioselectivity
• substrate structure
• Base
• leaving groups
• solvents
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An E2 reaction is also called a β-elimination or
a 1,2-elimination reaction:
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The removal of a proton and a halide ion is called
dehydrohalogenation:
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kinetics
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The hydrogen that is removed and the leaving group
both have to be in the axial position, therefore…
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Elimination of 2-bromopentane
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The Zaitsev Rule
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Exception to Zaitsev’s rule
Zaitsev product
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Based on leaving group
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Consider the elimination of 2-fluoropentane…
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E2 Reactions
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The E1 reaction, like the SN1 reaction, involves a
carbocation intermediate:
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kinetics
A unimolecular reaction:
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Stereochemistry of the E1 Reaction
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Carbocation rearrangement
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• 1-bromo 2,3 dimethyl cyclohexane
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Competition Between E2
and E1 Reactions
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A strong or a bulky base encourages elimination over
substitution
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Tertiary alkyl halides undergo only elimination under
SN2/E2 conditions:
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High temperature favors elimination over substitution:
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Synthesis Example
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Synthesis Example
Racemic
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Synthesis Example
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Synthesis Example
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The E2 reaction should be used if you want to
synthesize an alkene:
Hydroxide
Water
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Consecutive E2 Elimination Reactions
Requires a strong base NaNH2. Reaction carried out in liquid ammonia.
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