Organic Reaction mechanism

1. Substitution nucleophilic unimolecular (SN1) (The rate of reaction depends upon the concentration of only one reactant) SN1 reactions are generally carried out in polar protic solvents. The reaction between tert-butyl bromide and hydroxide ion yields tert-butyl alcohol.

Step I: formation of carbonium ion in polar solvents.

Step II The carbocation thus formed is then attacked by nucleophile.

In case of alkyl halides, 3 alkyl halides undergo S N1 reaction very fast because of the high stability of 3 carbocations.

Allylic and Benzylic halides show high reactivity towards the S N1 reaction. The carbocation thus formed gets stabilised through resonance.

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2. Substitution nucleophilic bimolecular (S N2) (The rate depends upon the concentration of both the reactants. Reaction between CH3Cl and hydroxide ion to yield methanol.

In this, incoming nucleophile interacts with alkyl halide causing the carbon- halide bond to break while forming a new carbon-OH bond. These two processes take place simultaneously in a single step and no intermediate is formed. As the reaction progresses, the bond between the nucleophile and the carbon atom starts forming, the bond between carbon atom and leaving group weakens. As this happens, the configuration of carbon atom gets inverted. This process is called as inversion of configuration. Tertiary halides are the least reactive because bulky groups hinder the approaching nucleophiles.

3. Elimination reactions When a haloalkane with -hydrogen atom is heated with alcoholic solution of potassium hydroxide, there is elimination of hydrogen atom from -carbon and a halogen atom from the -carbon atom. As a result, an alkene is formed as a product.

4. Hydration of alkenes to give alcohol

Step 1: Protonation of alkene to form carbocation by electrophilic attack of H 3O+ H2O + H+ H3O+

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5. Dehydration of Alcohols to give Ethene

Step 1: Formation of protonated alcohol.

Step 2: Formation of carbocation: It is the slowest step and hence, the rate determining step of the reaction.

Step 3: Formation of ethene by elimination of a proton.

6.

Dehydration of alcohol to give ether

Step 1: Protonation of alcohol to form carbonium ion CH3 CH2+ + H2O

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Step 2: Attack of nucleophile on carbonium ion

Step 3: Deprotonation to give final product.

7. CH3 O CH2CH3 + HI CH3I + CH3CH2OH Step 1: Protonation of ether

Step 2: Iodide is a good nucleophile. It attacks the least substituted carbon of the oxonium ion formed in step 1 and forms alkyl iodide. CH3I + CH3CH2 OH 8. Esterification

Step 1: Protonation of carboxylic acid

Step 2: Attack of nucleophile on carbonium ion

Step 3: deprotonation to give ester

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9.

Question 10.15: Write the mechanism of the following reaction:

10.

Question No 11.33

When 3-methylbutan-2-ol is treated with HBr, the following

reaction takes place:

Give a mechanism for this reaction The mechanism of the given reaction involves the following steps: Step 1: Protonation of alcohol

Step 2: Formation of 2 carbocation by the elimination of a water molecule

Step 3: Re-arrangement by the hydride-ion shift

Step 4: Nucleophilic attack

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