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 ! formation of carbonium ion in polar solvents.

Step

The carbocation thus formed is then attac"ed by nucleophile.

In case of alkyl halides, 3 alkyl halides undergo S N1 reaction !ery fast because of the high stability of 3 carbocations"

#llylic and $en%ylic halides show high reactivity towards the SN1 reaction. The carbocation thus formed gets stabilised through resonance.

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#. Substitution nucleophilic bimolecular (SN&) (The rate depends upon the concentration of both the reactants. $eaction between %&'%l and hydroxide ion to yield methanol.

n this( incoming nucleophile interacts with al"yl halide causing the carbon- halide bond to brea" while forming a new carbon-)& bond. These two processes ta"e place simultaneously in a single step and no intermediate is formed. *s the reaction progresses( the bond between the nucleophile and the carbon atom starts forming( the bond between carbon atom and leaving group wea"ens. *s this happens( the configuration of carbon atom gets inverted. This process is called as in!ersion of configuration. 'ertiary halides are the least reacti!e because bulky groups hinder the approaching nucleophiles"

'" (limination reactions +hen a haloal"ane 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. *s a result( an al"ene is formed as a product.

.. )ydration of alkenes to gi!e alcohol

Step 1! /rotonation of al"ene to form carbocation by electrophilic attac" of & ')0

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&#) 0 &0 &')0

1. *ehydration of #lcohols to gi!e (thene

Step 1! 2ormation of protonated alcohol.

Step #! 2ormation of carbocation! determining step of the reaction.

t is the slowest step and hence( the rate

Step '! 2ormation of ethene by elimination of a proton.

3.

*ehydration of alcohol to gi!e ether

Step 1! /rotonation of alcohol to form carbonium ion %&' 4 %&#+ 0 &#)

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Step #! *ttac" of nucleophile on carbonium ion

Step '! 5eprotonation to give final product.

6. ,)3 - O - ,)&,)3 + )I ,)3I + ,)3,)&O) Step 1! /rotonation of ether

Step #! odide is a good nucleophile. t attac"s the least substituted carbon of the oxonium ion formed in step 1 and forms al"yl iodide. %&' 0 %&'%&# 4 )& 7. (sterification

Step 1! /rotonation of carboxylic acid

Step #! *ttac" of nucleophile on carbonium ion

Step '! deprotonation to give ester

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8.

9uestion 1:.11! +rite the mechanism of the following reaction!

1:.

9uestion No 11.''

+hen '-methylbutan-#-ol is treated with &;r( the following

reaction ta"es place!

<ive a mechanism for this reaction The mechanism of the given reaction involves the following steps! Step 1! /rotonation of alcohol

Step #! 2ormation of #= carbocation by the elimination of a water molecule

Step '! $e-arrangement by the hydride-ion shift

Step .! Nucleophilic attac"

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