Está en la página 1de 3

Alkene

Chapt. 33 p.3

Example: Addition of bromine to propene in aqueous solution. H2C=CHCH3


Br2

The major produ t is not !!!!!!!!!!!!!!!!!!!!!!!!!!!! but !!!!!!!!!!!!!!!!!!!!!!! "ummar#: $ossible nu leophiles that an omplete %ith &r'
Br Br

Br + C C

(2) me hanism.

Addition of uns#mmetri al rea*ent to the C=C bond takes pla e +ia a similar Example: CH3CH=CHCH3 ,e hanism: (i) The C=C bond first atta ked b# the ele trophile- H. formin* a arbo ation.

(ii)

The arbo ation is atta ked b# the nu leophile- the Cl'

/eneralisation:

Addition of H#dro*en halide (H01 ) to an alkene.

The formation of the arbo ation requires a hi*h a ti+ation ener*# so that the rate is slo% and su h step is the rate determining step of the %hole rea tion. 2ther examples:

Alkene

Chapt. 33 p.2

,arko%nikoff4s 5ule : 2rientation of Addition Addition rea tion for C=C bond %ill take pla e so as to *i+e the most stable intermediate arbo ation.

Example: H#dro hlorination of propene The rea tion ma# in+ol+e t%o ompletin* additions (3) and (2)

Cl H3C
+

CH CH3 +

CH3CHClCH3

CH2=CHCH3

Cl +CH2CH2CH3 CH2Cl CH CH3

Addition (3) takes preferen e due to the hi*h stabilit# of the se ondar# arbo ation relati+e to the primar# arbo ation . A tuall# - addition (3) requires a lo%er a ti+ation ener*#.

Alkene

Chapt. 33 p.3

The order of stabilit# arbo ation is


R + C R R + C H H R C+ H H H + C H

most stable

least stable

6n rease in the number of ele tron releasin* (5 ) *roups tends to disperse the positi+e har*ethus stabili7in* the arbo ation.

También podría gustarte