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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: ALKENES and ALKYNES
Alkenes/Alkynes are named by adding the suffix modifier (-________/-________) to the end of the root.
Alkenes/alkynes receive ___________________ in numbering alkanes
Location is assigned to the first double bonded carbon
a.
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: STABILITY OF ALKENES
Since this is only possible with -R groups, the more substituted the alkene, the more ________________
EXAMPLE: Rank the following alkenes in order of lowest to highest heat of combustion.
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: ELIMINATION AND ZAITSEVS RULE
We often find that an elimination reaction can yield more than one unique alkene as a product.
The most stable product = ________________
Zaitsevs Rule explains that we will always favor the more substituted, thermodynamically stable product
UNLESS we are using a bulky base. A bulky base promotes the formation of a less substituted, kinetic product
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
PRACTICE: Predict ALL of the products of the following reactions. Label them as either major or minor if necessary.
a.
b.
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: DEHYDROHALOGENATION
The name given to an E2 reaction of an alkyl halide. The major product will depend upon the type of base used.
Mechanism:
EXAMPLE: Supply the mechanism and major/minor products for the following dehydrohalogenation reaction:
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: ACID-CATALYZED DEHYDRATION
Alcohols are terrible leaving groups, but in the presence of acid, they can be converted into an awesome leaving group
E2 -Hydrogen Elimination:
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: ACID-CATALYZED DEHYDRATION
Alcohols are terrible leaving groups, but in the presence of acid, they can be converted into an awesome leaving group
E1 Dehydration: 2o and 3o Alcohol Mechanism:
Protonation:
Carbocation Formation:
E1 -Hydrogen Elimination:
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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
PRACTICE: Provide the mechanism and products for the following dehydration reactions:
a.
b.
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