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ORGANIC - WADE 8E

CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES

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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

EXAMPLE: Name the following compound:

a.

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ORGANIC - WADE 8E
CH.7 - STRUCTURE AND SYNTHESIS OF ALKENES
CONCEPT: STABILITY OF ALKENES

Alkenes are also stabilized through _________________________________

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 = ________________

The least 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

The more R groups on the alcohol, the easier to dehydrate: _________________________________


The specific elimination mechanism depends on how easily the molecule will form a ______________________.

E2 Dehydration: 1o Alcohol Mechanism:


Protonation:

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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