!All Organic Reactions with Conditions!
Type of Reaction
Reaction Name
Conditions
Example Equation
Alkanes
Reduction
Preparation by
Hydrogenation of
Alkenes/ Cracking
Ni || 140°
OR Pt/Pd || r.t.
%& ( ∆
!′!′′=R'''R'''' +#$ *⎯⎯, !′!′′#-— -#!′′′!′′′′
89
Free Radical
Substitution
Free Radical Substitution
Mechanism
/012132140: 6-7$ *, 2-7 •<
-7 • +-#C →• -#E + #-7
=>4?3@32140: A
F
• -#E + -7$ → -#E -7 + -7 •
2-7 •→ -7$
GH>I1032140: J2 • -#E → #E -— -#E K
• -#E + -7 •→ -#E -7
Exc. Cl || UV
89
LMH>377: -7$ + -#C *, -#E -7 + #-7
Types of Substitutions
-#C + -7$ → -#E -7 + #-7
-#E -7 + -7$ → -#$ -7$ + #-7
-#$ -7$ + -7$ → -#-7E + #-7
-#-7E + -7$ → --7C + #-7
Alkenes
Elimination
EA
Preparation of Alkene/
Dehydration of Alcohol
Dehydrohalogenation of
Halogenoalkanes
(Markovnikov Involved)
Hydrohalogenation of
Alkenes (Markovnikov
Involved)
Halogenation of Alkenes
in CCl4
Halogenation of Alkenes
in H2O
Reduction
Excess c. H2SO4 || 170°
Al2O3 || 300–350°
!#$ -— -#$ L# *⎯⎯⎯⎯⎯⎯⎯⎯⎯, !#-=-#$ +#$ L
NaOH(alc) || Reflux
!#Y-— -#E *⎯⎯⎯⎯⎯⎯, !#-=-#$ +`3Y + #$ L
HX || r.t.
#$ -=-#$ + #Y *⎯, #E -— -#$ Y
NO PQR ST UVW°
ZSQN(\]^)
ZSQN(\a)
!#Y-— -#E *⎯⎯⎯⎯⎯, !-#(L#)—-#E +`3Y
bcd
X2 in CCl4 || r.t. ||
Decolor from red–
brown Br in CCl4
X2 in H2O || r.t. ||
Decolor from red–
brown Br(aq)
bcd(eefR
#$ -=-#$ + Y$ *⎯⎯⎯⎯⎯⎯, #$ Y-— -#$ Y
bcd
#$ -=-#$ + Y$ + #$ L *⎯, #$ Y-— -#$ L# +#Y
NO PQR g&hi ∆ ( gjhkl
Hydration of Alkenes
c. H2SO4 || H2O || ∆
#$ -=-#$ + #$ L *⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯, #E -— -#$ L#
Hydrogenation of Alkenes
H2 || Pt/Pd; r.t. or Ni;
140°
#$ -=-#$ + #$ *⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯, #E -— -#E
dh/dn jh bcd / %& jh UCW°
1
∆
-$ #C + 3L$ → 2-L$ + 2#$ L
In/Complete Combustion
Hydroxylation/Diol
Formation
EA
Nuc Substitution
Hydrolysis
Reduction
Nuc Substitution
Elimination favored:
• ∆
• ­ [NaOH]
• Solvent=Ethanol
Substitution favored:
• Solvent = H2O
Elimination
-$ #C + 2L$ → 2-L + 2#$ L
∆
Oxidation
ES
∆
O2 || ∆
Preparation from
Alcohols
Alkaline/Dil. KMnO4 ||
Cold || Purple decolors
to Brown ppt = MnO2
Halogenoalkanes
-$ #C + L$ → 2- + 2#$ L
#$ -=-#$ + [L] +#$ L → #$ L#-— -#$ L#
lkrf8s
PX3 || Reflux
PCl5 || r.t.
SOCl2 || Reflux*
HX
3!L# + =YE *⎯⎯⎯, 3!Y + #E =LC
bcd
!L# + =Yt *⎯, !Y + #Y + =LYE
bcd
!L# + uL-7$ *⎯, !Y + #Y + uL$
!L# + #Y → !Y + #$ L
Preparation from Alkenes
/ Hydrohalogenation of
Alkenes
Alkaline Hydrolysis/
Formation of Alcohol
HX || r.t.
!#$ -=-#$ + #Y *⎯, !#$ Y-— -#E
NaOH(aq) || Under
reflux
!Y *⎯⎯⎯⎯⎯⎯, !L# + Y w
Formation of Nitriles
KCN(alc) || Reflux
!Y + -` w *⎯⎯⎯⎯⎯⎯, !-` + Y w
H+(aq) || ∆
!-` *⎯⎯⎯, !-LL# + `#C (
LiAlH4 in dry ether ||
r.t. + H2O
!-` + 4[#] *⎯, !-#$ `#$ + `#C (
Excess NH3(alc) || ∆ ||
Pressure in Sealed Tube
!Y + `#E → !`#$ + #Y
Note: Excess {| forms higher order amines
Further Carboxylic Acid
Formation
Further Amine
Formation
Amine Formation
SN2 1° Halogenoalkanes
SN1 3° Halogenoalkanes
— (follows
Markovnikov)
bcd
ZSQN(Sv)
ZSQN(\]^)
x y( ∆
bcd
Polar Aprotic Solvents
(contain no H atoms
connected directly to an
EN atom. Not
capable of H-bonding)
Polar Protic Solvents
(capable of hydrogen
H–bonding.)
NaOH(alc) || Under
reflux
2
∆
}f~g
#E -— -#$ Y + L#— *⎯, #$ -(L#)— -#E + Y w
rj}h(x –
}f~g
-(!!′!′′)Y *⎯, - ( (!!′!′′) + Y w *⎯⎯⎯⎯⎯⎯, -(!!′!′′)L#
ZSQN(\a)
#E -— -#$ Y + `3L# *⎯⎯⎯⎯⎯, #$ -=-#$ + `3Å> + #$ L
Alcohols
NS
Reduction
Preparation from
Hydration
Alkenes
Cold c. H2SO4
H2O || ∆
#$ -=-#$ *⎯⎯⎯⎯⎯⎯⎯⎯⎯, #E -— -#$ — LuLE # *⎯⎯⎯⎯⎯, #E -— -#$ L#
Alkaline
Hydrolysis of
Halogenoalkanes
NaOH(alc) || Reflux
!Y *⎯⎯⎯⎯⎯⎯, !L# + Y w
LiAlH4 in dry ether ||
r.t. + H2O
OR NaBH4(alc)
OR H2/Pt/Pd; r.t. or
H2/Ni; 140°
Na(alc)
!-LL# + 4[#] *⎯, !-#$ L# + #$ L
Reduction of
Carboxylic Acids
Reduction of
Aldehydes —> 1°
Alcohols
Reduction of
Ketones—> 2°
Alcohols
ÇÉÑÖ Ü. NO PQR
àjhkl(∆
ZSQN(SÑÜ)
bcd
bcd
!-#L + 4[#] *⎯, !-#$ L#
bcd
!!′-=L + 4[#] *⎯, !!′-#— L#
Nuc Substitution
Formation of Haloalkanes
Reflux || ZnCl2 in case
of X=Cl
!L# + #Y → !Y + #$ L
Redox
Reaction with Na
Reactive Metal
2!L# + 2`3 → 2!Lw `3( + #$
Oxidation of 1° Alcohols
Oxidation
Elimination
Esterification
Esterification
Oxidation of 2° Alcohols
(No 3° as alpha carbon
does not have H atoms)
Dehydration to Alkenes
(follows Zaitsev=More
Alkyl groups=major)
Acylation (Ester
Formation) with
Carboxylic Acids
Acylation (Ester
Formation) with Acyl
Chlorides
Alc—> Aldehyde =
Distillation
Alc —> Carboxylic
acid = Reflux
Alc —> Ketone =
Reflux
[] jân ä&}h&f
[] jân bkrf8s
!-#$ L# *⎯⎯⎯⎯⎯⎯⎯⎯⎯, !-#=L *⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯, !-LL#
[] ( bkrf8s
!!′-#L# *⎯⎯⎯⎯⎯⎯⎯⎯, !!′-=L
[O] can be MnO4– OR Cr2O72–/H+
Excess c. H2SO4 || 170°
Al2O3 || 300–350°
!#$ -— -#$ L# *⎯⎯⎯⎯⎯⎯⎯⎯⎯, !#-=-#$ +#$ L
c. H2SO4 || ∆
!-LL# + !′L# åççççççé !-L— L!′ + #$ L
r.t.
!-L— -7 + !′L# → !-L— L!′ + #-7
NO PQR ST UVW°
ã.NO PQR (∆
3
Aldehydes & Ketones (Carbonyl Compounds)
Oxidation
Preparation from Alcohol
Reduction of Aldehydes
—> 1° Alcohols
Reduction
Reduction of Ketones—>
2° Alcohols
Alc—> Aldehyde =
Distillation
Alc —> Ketone =
Reflux
[O] can be MnO4–
OR Cr2O72–/H+ (orange
to green)
LiAlH4 in dry ether ||
r.t. + H2O
OR NaBH4(alc)
OR H2/Pt/Pd || r.t. or
H2/Ni || 140°
OR Na(alc)
[] jân ä&}h&f
!-#$ L# *⎯⎯⎯⎯⎯⎯⎯⎯⎯, !-#=L
[] jân bkrf8s
!!′-#L# *⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯, !!′-=L
bcd
!-#L + 4[#] *⎯, !-#$ L#
bcd
!!′-=L + 4[#] *⎯, !!′-#— L#
Carboxylic Acids, Esters, Acyl Chlorides and Anhydrides
Oxidation
Preparation of
Carboxylic Acids from
Oxidation of 1° Alcohol
Preparation of
Carboxylic Acids from
Oxidation of Aldehydes
∆ / bkrf8s
∆ | Reflux
Preparation of
Carboxylic Acids from
Hydrolysis of Nitriles
dil. H2SO4 / HCl
∆ | Reflux
NaOH(aq) followed by
dil. H2SO4 / HCl
∆ | Reflux
Acid-Base Reaction
Formation of
Carboxylate Salts
—
Esterification
Formation of Esters
c. H2SO4 || Reflux
Nuc Substitution
Formation of Acyl
Chlorides
SOCl2* or PCl5 || r.t.
Reduction || Hydrolysis
Reduction to 1° Alcohols
LiAlH4 in dry ether ||
r.t. + H2O
Hydrolysis
(Acidic/Basic)
!-#$ L# + 2[L] *⎯⎯⎯⎯⎯⎯, !-LL# + #$ L
MnO4–/ H+ OR Cr2O72–
/H+
∆ / bkrf8s
!-#=L + [L] *⎯⎯⎯⎯⎯⎯, !-LL#
lkrf8s
!-` + 2#$ L + #( *⎯⎯⎯, !-LL# + `#C (
lkrf8s
!-` + 2#$ L + L#– *⎯⎯⎯, !-LL– + `#E
xy
!-LL– *, !-LL#
!-LL# + `3L# → !-LL– `3( + #$ L
2!-LL# + `3$ -LE → 2!-LL– `3( + -L$ + #$ L
!-LL# + `3 → !-LL– `3( + 1ê2 #$
ã.NO PQR (bkrf8s
!-LL# + !′L# åçççççççççççé !-L— L!′ + #$ L
bcd
!-LL# + =-7t *⎯, !-L-7 + #-7 + =L-7E
bcd
!-LL# + uL-7$ *⎯, !-L-7 + #-7 + uL$ *
bcd
!-LL# + 4[#] *⎯, !-#$ L# + #$ L
4
%jïxR(ñóò)
Other reducing agents
can’t be used as
reduction is more
difficult
Esterification
Nuc Addition
Hydrolysis
Esterification
Hydrolysis
ë !-L-#$ íììî + 2[#] *⎯⎯⎯⎯⎯⎯⎯, !-#(L#)-#$ íììîô
!-L— -7 + !′L# → !-L— L!′ + #-7
Name: R’–yl R-oate
Alcohols
Acyl
Chlorides
+
Ammonia
!-L-7 + `#E → !-L`#$ + #-7
r.t.
1° Amines
!-L-7 + !′`#$ → !-L`#!′ + #-7
Name: N–R’–yl R–amide
Water
!-L-7 + #$ L → !-LL# + #-7
Preparation of Esters
from Carboxylic Acids +
Alcohols
Preparation of Esters
from Acyl Chlorides +
Alcohols
Hydrolysis of Esters
(Acidic)
Hydrolysis of Esters
(Alkaline)
ã.NO PQR (∆
c. H2SO4 || ∆
!-LL# + !′L# åççççççé !-L— L!′ + #$ L
r.t.
!-L— -7 + !′L# → !-L— L!′ + #-7
dil. H2SO4 / HCl
Reflux
NaOH(aq) followed by
Alcohol/ Carboxylate
Salt
Reflux
x y (bkrf8s
!-LL!′ + #$ L åççççççé !-LL# + !′L#
lkrf8s
!-LL!′ + `3L# *⎯⎯⎯, !-LL– `3( + !′L#
xy
!-LL– `3( *, !-LL# + `3(
Benzene
∆
2H$ SOC + HNOE → `L$ ( + 2#uLC – +#E L(
ES
Nitration of Benzene
c. H2SO4 || c. HNO3
|| >60°
5
ES
Bromination of Benzene
Br2 || Fe | FeBr3
Free Radical
Substitution
Chlorination of Benzene
Limited Cl2 || UV
Oxidation
Oxidation of
Alkylbenzene to
Carboxylic Acid
MnO4–/ H+ || ∆
OR MnO4–/ OH– || ∆ ||
H+
Extra Notes
Nucleophilic substitution — a nucleophile (contains a lone pair + negative charge) attacking a molecule that is electron deficient. This is
prevalent in halogenoalkanes due to the polar bond.
Electrophilic addition —when electrophiles (electron deficient/cations) molecules are combined with another molecule. And usually this happens
with alkenes. Alkenes have a double bond where pi bonds are present, and here it is dense
in electrons.
Polymerization — is the merging of several alkenes.
• Monomers → Polymers which are huge molecules with repeating units Ethene →
Polyethene.
o The doubles bonds are broken from ethene and actually a really long chain of
alkane is formed. Propene → Polypropylene
• Condensation polymerization can only happen when there are two reactive
functional groups. You must form chains on both ends! But addition polymerization
require double bond(s).
6
Further Reactions
Key:
|| – And
| – Or
7