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Chapt. 33 p.3
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)
/eneralisation:
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
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
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.