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1 Roh Carboxylic Acids: H Cro

The document provides an overview of common organic reactions involving aromatic compounds (arenes). It outlines methods for halogenating, nitrating, and sulfonating arenes. It also describes processes for alkylating arenes using Friedel-Crafts reactions and synthesizing arylethers, benzoic acids, benzyl halides, and benzyl bromides from arenes. The final section discusses hydrogenation reactions of arenes catalyzed by platinum or palladium, which can form either the desired saturated product or unwanted side products.

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99 views15 pages

1 Roh Carboxylic Acids: H Cro

The document provides an overview of common organic reactions involving aromatic compounds (arenes). It outlines methods for halogenating, nitrating, and sulfonating arenes. It also describes processes for alkylating arenes using Friedel-Crafts reactions and synthesizing arylethers, benzoic acids, benzyl halides, and benzyl bromides from arenes. The final section discusses hydrogenation reactions of arenes catalyzed by platinum or palladium, which can form either the desired saturated product or unwanted side products.

Uploaded by

andrewwroble
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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O

H2CrO4
R

OH

or Na2Cr2O7 /H2SO4
or CrO3/H2SO4

1o ROH

OH

Carboxylic Acids

OH

H2CrO4
R'

or Na2Cr2O7 /H2SO4
or CrO3/H2SO4

2o ROH

R
R'
Ketones

PCC or PDC
R

OH

CH2Cl2

1 ROH

Aldehydes

OH

O
PCC or PDC

R'

CH2Cl2

2 ROH

R
R'
Ketones

Nao or Ko
R

OH
ROH (solvent)

2R

O Na

NaH
OH

2R
ether; THF or alkanes

O Na + H2

(reaction is irreversible)

OH

HX
R''

R'

R'

3o ROH

3 Halides

OH

HX (conc)
R

R''

R (H)

Heat

R (H)
H

1o & 2o Halides

1o & 2o ROH

OH

Cl
SOCl2

R (H)

Pyridine or N(Et)3

R (H)

1o & 2o ROH

1o & 2o Chloride

OH

R (H)
H3O+

R
CH2

R (H)
R (H)

R
CH

-H2O

Alkene
(Zaitsev's rule)

ROH
OH

OR'

1) Nao
R

R (H)
R (H)
ROH

R (H)

2) R'X
o

R
o

1 or 2

R (H)
R (H)
Ether

OH + H

H2SO4
OR'

R
C

CH2 + H

H2SO4
OR'

OR'

Heat

OR'
C

Heat

CH2H

2 H2C

CH2

O2
2 H2C

Ag

R
C

CH2

CH2

RCO3H
C

CH2Cl2

CH2

R
R

OH

NaOH
C

CH2

C
R

O
C
R
R

CH2

CH2

OH

H3O+

C
R
R

CH2
OH

O
C

CH2

OH

Na+CNH2O

(H)R

CH2
CN

(H)R

O
C

CH2

2) H2O

(H)R

OH

1) Na+ C CH

(H)R

O
C

CH2
CH

OH
NH3

CH2

(H)R

CH2
NH2

(H)R

Second Semester
Chap 15:
Mg
R

Mg

ether or THF

MgBr

Mg
ether or THF

OH

O
1) R"
R

(H)R

CH2

2) H3O+

Mg

X
R

(H)R

CH2
R"

OH
1) R"

Mg

C
R

2) H3O+

R(H)

R(H)
R"

R'

R2CuLi

R'

ether or THF

R
+

R2CuLi

ether or THF

Cl3CH + K+ -OtBu

Cl2C
used immediately

R
Cl2C

H
Cl

+
R

Cl
Stereospecific Rxn

O
H2CrO4 (aq)

C
R

aldehyde

or Na2Cr2O7 /H2SO4
or CrO3/H2SO4

C
R

Carboxylic Acid

O
2

O
O2

C
R

OH

aldehyde

C
R

OH

Carboxylic Acid

OH
1) LiAlH4

H(R)

2) H2O

H
H(R)

Carbonyl

Alcohol
O

OH
NaBH4

C
R

H(R)

MeOH; H2O

C
R

Carbonyl

H
H(R)

Alcohol
O

OH
H2

C
R

H(R)

RT, 2 atm

H
H(R)

Carbonyl

Alcohol

O
H2C

2 H2

H2
C

C
C
H

Ni

H(R)

H
C

H
H
H(R)

Carbonyl

Alcohol

C
R

C
H(R)

Zn(Hg), HCl

Carbonyl

H
H(R)

Hydrocarbon
O
C
R

N2H4; KOH
heat;
H(R)

Carbonyl

HO

C
OH

H
H(R)

Hydrocarbon

Nucleophilic Acyl Substitution

O
R'OH

C
R

OH

(cat)

OR'

Carboxylic Acid

Ester

O
HOH

C
R

+ HCl

Cl

Acid Chloride

OH

Carboxylic Acid

+ HOH

H2O

H+ (cat)

C
OH

Carboxylic Acid

Acid Anhydride

H2O
O

H+ (cat)
O

C
R

OR'
C

Ester

NaOH

Carboxylic Acid

O
Na
C
R

OH

H3O

R'OH

H2O
O

H+ (cat)
O

C
R

NH2
C

Amide

NaOH

OH

NH4

Carboxylic Acid

O
H3O+

Na
C
R

H2O
O

H+ (cat)
O

C
R

NH2
C

Amide

NaOH

NH4

OH

Carboxylic Acid

O
+

Na

H3O

C
R

O
R'OH

C
R

Cl

Acid Chloride

+ HCl

C
OR'
Ester

R'OH
R

O
Acid Anhydride

C
R

C
OR'

Ester

HO

Carboxylic Acid

O
R''OH

OR'
Ester

R'OH

OR''
Ester

Alcohol

O
Cl

2 R'NH2

C
R

Cl

Acid Chloride

R'NH3

NHR'

Ammonium
Hydrochloride Salt

Amide

O
2 R'NH2

R'NH3

Acid Anhydride

NHR'

O
2 R'NH2

C
R

OR''

Ester

NHR'

R"OH
Alcohol

Amide

Na
C
R

+
Cl

Acid Chloride

C
O

C
R

Sodium
Carboxylate Salt

Ammonium
Carboxylate Salt

Amide

C
O

Acid Anhydride

OH
1) 2 eq R'MgBr

C
R

OR'

R'

2) H3O+

Ester

R'

3o Alcohol

OH
1) 2 eq R'Li

C
R

OR'

R'

2) H3O+

Ester

+ HOR'

R'

3o Alcohol

O
1) (R')2CuLi

C
R

+ HOR'

Cl

2) H3O+

Acid Chloride

R'

Ketones

OH
1) LAH

C
R

OR'

2) H3O+

C
R

Ester

H
H

1o Alcohol

O
1) DiBAlH

C
R

OR'

2) H3O+

Ester
2AlH2

C
R

Aldehydes

O
H2
C

1) LAH
C
R

2) H3O+

NH2

NH2
-N(H)R2

-N(H)R2
Amide

Amines

H2
C

1) LAH
R

2) H3O+

NH2

Nitrile
Amines

O
C
R

H3O+

H(R')

OH

H3O+

+
HC
O

C
R

OH-

H(R')

H(R')

Na+-OR

C
OR

C
H3C

OR

ROH

OH

-hydroxycarbonyl

H3C

H(R')

-unsaturated carbonyl

C
C
H2
-ketoester

+ ROH
OR

1) Na+-OR / ROH

C
H2

C
R

OR

2)

R"

O
C
HC

OR

R"

-ketoester

O
N

N
H

Br
H

Br

HCl( aq)

R
-substituted ketone

Enamines

Iminium Salt

Chemistry of Acidic Methylene compounds (Acetoacetic & Malonic Ester Synthesis):


O

1) Na+-OR / ROH

C
H2

OR

C
R

2)

R"

O
C
HC

R"

-ketoester

1) NaOH( aq)

2) H3O+( aq)
3) heat

HC
R"

OR

OR

C
R

CH2
O
R"
This is irreversible and leds to
ketone products

Conjugate Addition (1,4 addition or Michael Addition):


1

Nu

Nu

3
2

Nu

OH

The Robinson Ring Anulation:

Stage 1:
Michael Addition

H2CH
O

Stage 2:
Intramolecular
Aldol Condensation

Chapter 22
X
X2
FeX3

Arenes

Halogenated arenes

NO2
HNO3
H2SO4

Arenes

Nitro arenes
SO3H
SO3
H2SO4

Arenes

Arene Sulfonic Acids

R
R

Cl

AlCl3
Arenes

Alkylbenzenes
O

O
C
R

Cl
AlCl3

Arenes

Acylbenzenes

OH
H2
C
R

Phenol

O
Cl

R
C
H2

NaOH(aq);
CH2Cl2;
Bu4N+BrArylethers

CHR

C
OH

H2CrO4
or
KMnO4
Benzoic Acids

Arene

X
CHR2

R2C

X2
heat or h

Arene

Benzyl Halides
Br
CHR2

R2C

NBS
peroxides

Arene

Benzyl Bromides

H2
C

H2
O

Pt or Pd

HO

the
desired
product

CH3

the side product

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