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ORGANICCHEMISTRYMECHANISMSUMMARY

FREERADICALSUBSTITUTION(FRS)

Exemplifed by !e "#b"i#i$% $& me!'%e by !l$i%e

Sep *+ I%ii'i$%

Cl,Cl #- Cl. / Cl.

Sep 0+ 1$p'2'i$%

') Cl. / CH3CH4. / HClb) CH4. / Cl0CH4Cl / Cl.T!e% (')5 (b)5 (')5 (b)6

Sep 4+ Temi%'i$%

') Cl. / Cl. Cl0b) CH4. / Cl. CH4Cl) CH4. / CH4. CH4CH4

ELECTRO1HILICADDITION

Exemplifed by !e 'ddii$% $& HB $ '% 'l7e%e

Step 1C C

H

HH

H

+

H Br s l o w CH

H

C

H H

H

+ + Br

-+

'b$'i$%i%emedi'e

Step 2f a s t

CH

H

C

H H

H

++ :Br

-

C C H

Br

H

H

H

H

ELECTRO1HILICAROMATICSUBSTITUTION

Exemplifed by !e 'ddii$% $& NO0$ be%8e%e

Step 1Ge%e'i$%

$&ele$p!ile

HNO4/ 0H0SO39 NO0// H4O

// 0HSO3:

Step 2Ele$p!ili

''7

+ s l o w

NO2H

+NO2+

be%8$%i#m i$%

Step 3L$"" $&p$$%

NO2H

+f a s t

NO2

++HSO4-

H2SO4

NUCLEO1HILICSUBSTITUTION; SN0 ; ONESTE1

Nu-: C

R2R1

X

R3

+

C

R2R1

X

R3

Nu

C

R2R1

Nu

R3

+ X-

pe%'-'le% '%"ii$% "'e

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NUCLEO1HILICSUBSTITUTION; SN* ; TCN 9 >// CN:

Step 2N#le$p!ili

''7C O

CH3

H

+ :CN- s l o w C O

-

CN

CH3

H

+

Step 31$$%'i$%

C O-

CN

CH3

H

+ H C N

f a s tC OH

CN

CH3

H

+ CN-

Cy'%$!ydi%