ORGANIC - KLEIN 3E CH.8 - ADDITION REACTIONS OF...

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ORGANIC - KLEIN 3E

CH.8 - ADDITION REACTIONS OF ALKENES

CONCEPT: GENERAL MECHANISM

□ Addition reactions are ones in which 1 ______ bond is broken and 2 new ______ bonds are formed.

● They are the inverse of ___________________ reactions

EXAMPLE: Provide the mechanism for the following addition reaction.

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CONCEPT: MARKOVNIKOV’S RULE

□ When we try to perform addition on asymmetric double bonds, we now get two possible products.

● Markovnikov’s Rule predicts that the carbocation will ALWAYS form on the _________ _______________ carbon


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CONCEPT: HYDROHALOGENATION

General Reaction:


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CONCEPT: RADICAL HYDROHALOGENATION

□ Recall the hydrohalogenation mechanism:

● ____________________ intermediate

● _____________________ addition of bromine

Compare to the radical mechanism that predominates in the presence of peroxide:

● ____________________ intermediate

● _____________________ addition of bromine

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EXAMPLE: Provide the complete mechanism for the following radical hydrohalogenation.

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CONCEPT: ACID-CATALYZED HYDRATION

● Same reagents as acid-catalyzed dehydration, except starting with a _____________ __________ instead of an alcohol.

● Same as the general mechanism hydrohalogenation, except with _____________ as the nucleophile

● Remember that EVERY acid-cat. mechanism begins with ________________ and ends with ________________

General Reaction:


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PRACTICE: Provide the mechanism and predict the product of the following reaction.

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CONCEPT: OXYMERCURATION-REDUCTION

General Reaction:

Mechanism:

1. Electrophilic Addition

2. Nucleophilic Substitution (SN2)

3. Reduction (demurcuration)

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PRACTICE: Provide the mechanism and predict the product of the following reactions.

a.

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CONCEPT: HYDROBORATION-OXIDATION

General Reaction:

Mechanism:


2. Oxidation

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a.

b.

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CONCEPT: CATALYTIC HYDROGENATION AND WILKINSON’S CATALYST

General Reaction:

PRACTICE: Provide the products for the following reaction.

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CONCEPT: HALOGENATION

General Reaction:

Mechanism:



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CONCEPT: HALOHYDRIN FORMATION

General Reaction:

Mechanism:



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a.

b.

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CONCEPT: EPOXIDATION

□ Epoxides are added to double bonds using _________________ ____________

● Common reagents are _____________ and ___________

Mechanism:

□ Epoxides can also be generated though an intramolecular _______ reaction of halohydrins.

Mechanism:

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CONCEPT: EPOXIDE RING OPENING

1. Acid-Catalyzed Ring Opening

Following protonation of the epoxide, the nucleophile will attack the side of the ring with the most ___________ character:

2. Base-Catalyzed Ring Opening

The strong nucleophile will attack the side of the ring that is ___________ substituted

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CONCEPT: SYN VICINAL DIHYDROXYLATION

General Reaction:

EXAMPLE: Predict the product for the following multi-step reaction.

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CONCEPT: WEAK OXIDATIVE CLEAVAGE

Ozonolysis: Ketones + Aldehydes + Formaldehyde

PRACTICE: Predict the products of the following reaction

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CONCEPT: OZONOLYSIS – FULL MECHANISM

The mechanism for ozonolysis proceeds through multiple intermediates.

●Ozonolysis is combined with either a reductive, or an oxidative workup

□ Reductive workup: S(CH3)2 or Zn/HOAc

□ Oxidative Workup: H2O2

Ozonolysis Mechanism:

Reductive Workup Mechanism:

Oxidative Workup Mechanism:

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PRACTICE: Predict the products and show the full mechanism for the following reaction

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CONCEPT: OXIDATIVE CLEAVAGE

Strong Oxidative Cleavage: Ketones + Carboxylic Acid + Carbon Dioxide

PRACTICE: Predict the product of the following reaction.

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ORGANIC - KLEIN 3E CH.8 - ADDITION REACTIONS OF...

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