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Chapt. 31 p.1
Example: Addition of bromine to propene in aqueous solution. H2C=CHCH3
The major product is not ____________________________ but _______________________ Summary: Possible nucleophiles that can complete with BrBr Br
Br + C C
Addition of unsymmetrical reagent to the C=C bond takes place via a similar Example: CH3CH=CHCH3 Mechanism: (i) The C=C bond first attacked by the electrophile, H+ forming a carbocation.
The carbocation is attacked by the nucleophile, the Cl-
Addition of Hydrogen halide (H—X ) to an alkene.
The formation of the carbocation requires a high activation energy so that the rate is slow and such step is the rate determining step of the whole reaction. Other examples:
Alkene Chapt.2 Markownikoff’s Rule : Orientation of Addition Addition reaction for C=C bond will take place so as to give the most stable intermediate carbocation. Actually . addition (1) requires a lower activation energy. Example: Hydrochlorination of propene The reaction may involve two completing additions (1) and (2) Cl H3C + CH CH3 + CH3CHClCH3 CH2=CHCH3 + H Cl +CH2CH2CH3 CH2Cl CH CH3 Addition (1) takes preference due to the high stability of the secondary carbocation relative to the primary carbocation . 31 p. .
3 The order of stability carbocation is R + C R R + C H H R C+ H H H + C H R R most stable least stable Increase in the number of electron releasing (R ) groups tends to disperse the positive charge.Alkene Chapt. . 31 p. thus stabilizing the carbocation.