Doug Young

Identifying Reactions
Identify each of the following reactions as a substitution, an addition (nucleophilic or
electrophilic), an elimination, an oxidation or a reduction. Note: Some reactions can fall
under more than one category. You can also guess as to which reagents should be used.

1) Cl OH
Substitution
(Sn1)

H3O+

2) OH O
Oxidation

CrO3, H2O
H2SO4

Substitution SO3H
3)
(aka: Addition/Elimination)

SO3, H2SO4

4) Br
Elimination

NaOCH3
(Any small base)

5) Cl
Elimination
Cl
NaNH2

6) Br
(Electrophilic) Addition

Br2
Br

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(Nucleophilic) Addition
7) O ALSO a Reduction HO CH2CH3
1) CH3CH2MgBr / Et2O

2) H3O+

(Nucleophilic) Addition
8) ALSO a Reduction
HO
O
NaBH4
EtOH

9) O Substition O (Technically this is an

Addition/Elimination reaction,
treat it as such on the MCAT)
HOCH3 R OCH3
R Cl

10) Reduction
R C N R CH2NH2
1) LiAlH4 / Et2O
2) H3O+

11) Substituion (SN2) HO

F

NaOH

12) O (Nucleophilic) Addition

Note: not a Redox reaction O
O
OH
HO
H3O+

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13)
OH Elimination (E1)

H2SO4

14) Substitution
(Radical Reaction!)
Br2
h Br

15) I
(Electrophilic) Addition

HI
@ 0oC

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