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Development of Complex Curricula for Molecular Bionics and Infobionics Programs within a consortial* framework**

Consortium leader

PETER PAZMANY CATHOLIC UNIVERSITY

Consortium members

SEMMELWEIS UNIVERSITY, DIALOG CAMPUS PUBLISHER

The Project has been realised with the support of the European Union and has been co-financed by the European Social Fund ***

PETER PAZMANY CATHOLIC UNIVERSITY SEMMELWEIS

UNIVERSITY

(2)

Organic an Biochemistry

The main classes of compounds and their reactions

www.se.hu

(Szerves és Biokémia )

(A legfontosabb reakcióink és vegyülettípusaink)

Compiled by dr. Péter Mátyus

with contribution by dr. Gábor Krajsovszky

(3)

Table of Contents

semmelweis-egyetem.hu

Organic and Biochemistry: Reactions and Compounds

1. Alkanes 4 – 5

2. Alkenes 6 – 7

3. Alkynes 8 – 8

4. Arenes 9 – 9

5. Aryl diazonium compounds 10 – 10

6. Alkyl halides 11 – 16

7. Alcohols 17 – 23

8. Oxo compounds 24 – 26

(4)

Alkanes Alkenes

Carboaromatics Alkyl halogenides Alcohols

Ethers

Reactions – Transformation of functional groups I

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

(5)

Alkane – alkyl halogenide

Organic and Biochemistry: reactions and compounds

semmelweis-egyetem.hu

Alkenes Alkanes Alcohols

Ethers Organometallic

compounds

Esters

Thiols Amines

Nitriles Alkylated products

Alkenes Organometallic Primary

Alkyl

halides

(6)

Alkyl halogenide - alkane

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C Br H

C H H Bu

3

SnH

AIBN

Br

Bu

3

Sn Bu

3

SnH

+ Bu

3

Sn

AIBN = azobisisobutyronitrile

(7)

Alkenes (olefines)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Alkenes

Alkanes Alkyl halides Alcohols

1,2-Dioles Alkynes

Aldehydes

and ketones Amines Epoxides Halohydrins

(8)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C C C

H

E

+

reacts with electrophiles (Markownikoff addition) and radicals

carbocations and radicals delocalized and stabilized by the adjecent double bond reactions with dienes in

Diels-Alder reactions

(9)

Alkynes

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Alkynes

Alkanes Alkenes

Dimers, trimers and tetramers

Alkyl halides Ketones

Ethynyl alcohols

Organometallic

compounds

(10)

Aromatic compounds

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Arenes

Arylamines Aryl halides

Aryl carboxylic acids

Aryl aldehydes and ketones

Arylalkanes

Aryl diazonium compounds

Aryl

nitro compounds

Aryl sulfonic acids

Phenols Quinones

Amides Imines

(11)

Aryl diazonium compounds

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Aryl diazonium compounds

Arenes Phenols Aryl nitriles

Aryl fluorides Aryl halides (Cl, Br, I) Arylamines

Diazo compounds

Aryl hydrazines

(12)

Alkyl halogenides

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

(13)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

H C

C halogen elimination

nucleophilic substitution

metal insertion

radical attack

(14)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Me

C Cl Me

Me C+

Me

Me Me Me

C OH Me

Me

+

Me C O H

Me

Me

+

Cl-

slow H2O

Me (CH2)2

CH3 O

H -

Me (CH2)2

CH2 Cl OH

-

Me

(CH2)2 CH2 O

H

+

Cl-

Me

C Br Me

Me C+

CH2

Me Me H

slow O H -

C CH2

Me Me

- H CH CH

CH3

Br

+

CH CH CH

+

Br-

S

N

1

S

N

2

E

1

E

2

Nucleophilic substitutions

Elimination reactions

(15)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C Hal H

C O H

H

C RO

H C

O H S

+

Me Me

C O

H C

R O

Me

2

S + O C

Me

2

S=O K

2

CO

3

(or OH

-

)

ROH, Ag

2

O RCO

2-

(Cs

+

or Ag

+

salt)

(16)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C Hal H

C C

H N

C C

H RC

C

-

N

C

-

RC C

-

M

+

C C H C

C C

H O

R

C C

-

O

R

(17)

The versatile Grignard reagent: its application

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

R

1

MgX

R

1

H R

1

CH

2

OH R

1

CO

2

H

CH(OH) R

1

R

2

C R

1

OH R

3

R

2

C

R

1

OH R

2

R

1

CH(OH) R

1

R

1

H

+

HCHO R

2

CHO CO

2

HCO

2

Et

R

2

CO

2

Et C O

R

2

R

3

(18)

Alcohols

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

(19)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

CH 2 CH 2 CH 2 OH C OH CH 3

H C

H 3 C OH

CH 3

CH 3 C

H 3

Primary Secondary Tertiary

propan-1-ol n-propyl alcohol

propan-2-ol isopropyl alcohol

2-methylpropan-2-ol

t-butyl alcohol

(20)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C O C

H H

H elimination

nucleophilic substitution of derivatives

oxidative removal

basic lone pair

weakly acidic

(21)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Alcohols Amines

Alkyl halides

Aldehydes and ketones Alkenes

Alkanes

Alkylated

products

(22)

Ethers: oxirane (epoxide)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C

C C

H O

C

may rearrange

may eliminate

C-O bond may cleave with carbocation formation; this can initiate rearrangements, cyclizations or elimination reactions

nucleophilic substitution at either centre, depending on the reagent

lone pair reacts with

acids, Lewis acids and

other electrophiles

(23)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Epoxides

Alkenes

Aldehydes and ketones

Ketols Alkylated

products Alcohols

Halohydrins

1,2-Diols

(24)

Carbonyl compounds I

- aldehydes - ketones

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

(25)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Aldehydes and ketones Ketols and

thioketals

Alkanes

Alkenes

Hydrazones

Alcohols Carboxylic acids

Lactones and esters

Oximes

(26)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

O C H C H

δ+ δ−

nucleophilic attack

may be oxidized

protons and Lewis acids add to O, increasing

the electron deficiency of the C

rendered weakly acidic,

anion is resonance stabilized

(27)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Enols and enolate anions C-Alkylated products O-Ethers

α-Bromo ketones

α,β-Unsaturated ketones

α-Hydroxy ketones and α-diketones

β-Keto esters β-Diketones

β-Hydroxy ketones

(28)

Carbonyl compounds II

- Carboxylic acids and derivatives

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

(29)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

Carboxylic acids

Alcohols

Alkyl halides

Amines Amides Acid anhydrides

Esters

Acyl halides

Aldehydes

(30)

Some C-H acids

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

(31)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C O

O H C

O N H

C O

C H weakly acidic

acidic

(32)

Organic and Biochemistry: Reactions and Compounds

semmelweis-egyetem.hu

C N H

O C N

OH

C N

H O

O

C N OH O

C P H

O

C S H

O

C S H

O

O weakly acidic

weakly acidic

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