SUMMARY OF ORGANIC CHEMISTRY REACTIONS
FUNCTIONAL REACTION
GROUP NAME
TYPE
and STRUCTURE
All that contain C, H, O Combustion
Hydrocarbons,
RCH2CH3
(complete &
incomplete)
Alcohols, RCH2OH
CONDITIONS
PRODUCT(S)
Oxygen (O2) is always a CO2 + H2O (complete)
reactant.
C+ CO + CO2 + H2O
Initiated by heat = ∆
(incomplete)
(including this symbol is
optional)
COMMENTS
Must balance these
equations. Use molecular
formula in equation.
Aldehydes/ketones are
constitutional isomers
esters, carboxylic
acids R1 CO2R2
Carboxylic acids/ esters are
constitutional isomers
Addition
Addition
H2O in acid (H+)
1o, 2o or 3o alcohol
EXAMPLE
∆
2C2H6 + 7O2  4CO2 + 6H2O
C2H4 + 3O2  2CO2 + 2H2O
2CH3OH + 3O2  2CO2 + 4H2O
aldehydes, ketones,
R1C(O)R2
Alkenes
RCH=CH2
Page 1 of 4
Hydration reaction
follows Markovnikoff’s
Rule – rich get richer
C3H6O + 4O2  3CO2 + 3H2O
2C3H6O2 + 7O2  6CO2 + 6H2O
OH
|
H-C-CH3
|
CH3
Reverse of dehydration of
alcohol reaction (Rxn # 10)
H+
H-C=CH2 + H2O 
|
CH3
CH2=CH2  CH3CH3
H2
alkane
Hydrogenation reaction
HCl , HBr, HI
haloalkane
Hydrohalogenation reaction
follows Markovnikoff’s
Rule
Addition
H-C=CH2 + HBr 
|
CH3
Br
|
H-C-CH3
|
CH3
Addition
Cl2 , Br2 , I2
dihaloalkane
Halogenation reaction
H-C=CH2 + Br2 
|
CH3
Br Br
| |
H-C-CH2
|
CH3
SUMMARY OF ORGANIC CHEMISTRY REACTIONS (continued)
FUNCTIONAL
GROUP NAME
and
STRUCTURE
Alcohols –
1o RCH2OH
REACTION
TYPE
Elimination ,
dehydration –
CONDITIONS
PRODUCT(S)
COMMENTS
Page 2 of 4
EXAMPLE
Acid catalyzed (H+) with Most substituted alkene
heat.
Saytseff’s rule – poor get
poorer (this C atom is
bonded to only 2Hs – the
others are bonded to 3)
OH
|
H+
CH3-CH2-C-CH3  CH3-CH=C-CH3 + H2O
|
|
CH3
CH3
Base catalyzed (OH-)
with heat
if asymmetric can form
several products (cis and
trans as well)
NaOCH2CH3
CH3CH2(Br)

loss of H2O
2o RCHOHCH3
3o RC(CH3)2OH
Haloalkanes
Elimination
alkene and alcohol
alcohol
Substitution
reacting with binary acid haloalkane and water
(e.g. HCl, HI, HF)
base that releases OHalcohol
UV catalyzed
a number of isomers
haloalkane
alkane
substitution
substitution
benzene
substitution
different catalysts
possible
Oxidation
[O] conditions.
Some oxidizing agents = 1o give aldehydes first,
CrO3 , H2CrO4 , K2Cr2O7 then carboxylic acids
a halobenzene
ethene and others
ethanol + HF  fluoroethane + H2O
number of products
depends on amount of
halogen present
same as above
1-chloropropane + OH  propan-1-ol
see textbook, page 103 for example
see textbook, page 103 for an example
alcohol
OH
O
O
| [O]
|| [O]
||
CH3-CH2  CH3-CH  CH3-COH
Reverse of reduction of
aldehyde or ketone
reaction
2o give ketones
OH
|
[O]
CH3-C-CH3  NR
|
CH3
3o No Reaction
aldehyde or ketone
reduction
alkene
reduction
[H] reducing conditions
eg. LiAlH4 or H2
OH
O
|
[O]
||
CH3-CH2-CH-CH3  CH3-CH2-C-CH3
alcohol
reverse of oxidation
pentanal + [H]  pentan-1-ol
alkane
also know as
hydrogenation or
saturation
ethane + [H]  ethane
SUMMARY OF ORGANIC CHEMISTRY REACTIONS (continued)
FUNCTIONAL
GROUP NAME
and
STRUCTURE
REACTION
TYPE
CONDITIONS
PRODUCT(S)
Condensation Reaction of any
ester
(esterification) carboxylic acid with any
alcohol , catalyzed by
acid and heated
Condensation- Acid + amine + heat.
amide product
Reaction with 1o gives a
2o amide. Reaction with
2o amine gives 3o amide
COMMENTS
Catalyzed by acid.
Anhydride + alcohol
gives ester product
without acid catalysis
Same reaction as amide
formation reaction
already described in
amines
Reaction with 3o amine
does not give amide, only
neutralization product.
Ester
R1-C=O
|
OR2
Hydrolysis
Ester + acid or base +
heat
Reverse of esterification
reaction
Acid
catalysiscarboxylic
acid + alcohol
Base catalysis
carboxylate ion + alcohol
Reverse of ester forming
reaction
Page 3 of 4
EXAMPLE
O
O
||
H+
||
CH3OH + CH3-COH  CH3-COCH3 + H2O
O O
O
O
||
||
||
||
H-C-O-C-H + CH3-OH  H-COH + CH3-O-C-H
ester
O
O
||
∆
||
CH3NH2 + CH3-COH  CH3-CNHCH3 + H2O
O
O
||
∆
||
(CH3)3N + CH3-COH  CH3-CO- + (CH3)3NH+
not an amide+
O
O
||
H+
||
CH3-COCH3 + H2O  CH3OH + CH3-COH
O
O
||
OH||
CH3-COCH3  CH3OH + CH3-CO-
SUMMARY OF ORGANIC CHEMISTRY REACTIONS (continued)
FUNCTIONAL
GROUP NAME
and
STRUCTURE
REACTION
TYPE
Condensation
– amide
formation
CONDITIONS
PRODUCT(S)
COMMENTS
O
O
||
∆
||
CH3NH2 + CH3-COH  CH3-CNHCH3 + H2O
Reaction with 2o amine gives
3o amide (rxn not shown)
O
O
||
∆
||
(CH3)3N + CH3-COH  CH3-CO- + (CH3)3NH+
not an amide+
Reaction with 3o amine does
not give amide, only
neutralization products.
Hydrolysis
Acid or base catalzyed
Acid catalysis
carboxylic acid +
ammonium ion
Base catalysis
carboxylate ion + amine
EXAMPLE
O
O
||
∆
||
NH3 + CH3-COH  CH3-CNH2 + H2O
Reaction with carboxylic
Ammonia + carboxylic acid
acid Requires heat.
gives primary amide
Otherwise only
neutralization occurs
Reaction with 1o amine
gives a 2o amide.
Amides
R-C=O
|
NH2
Page 4 of 4
Reverse of amide forming
reaction (Rxn # 18 and 2124 above)
O
||
CH3-CNHCH3
H+

O
||
CH3-COH + CH3NH4+
O
||
CH3-CNHCH3
O
OH||

CH3-CO- + CH3NH2