Organic chemistry 9 amines and amides
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. (Ph.D. Sci. & Tech. Education)

Email: ssaksri@sci.ubu.ac.thOffice: SC 1381

(Organic Chemistry) 9 (Amines and Amides)

.. (Ph.D. Organic Chemistry)Email: jchote@sci.ubu.ac.thOffice: Chem 1208


(Learning Objectives)

...


9.1

  • (amine) ................................

  • (amide) ( 8) .

aliphatic amine aromatic amine

..


(amide)


(alkaloids) ()

amine amide


amine amide

paracetamol (acetaminophen)

.....................

Chlorpheniramine .............

..

ephedrine

............

.............

(?)

amphetamine

.................


quinine

Thiamine (.)

..

..

amine amide


9.2

1.

  • amine

.amine

amine

.propylamine

amine


2. IUPAC

  • N nitrogen atom

(prefix)

[substituent(s)]

parent structure

alkane

(suffix)

[functional group(s)]

alkane

amine

=

+

hexane

amine

=

+


amine

..

amine

..

1-butanamine

N-ethyl-3-hexanamine

3-chloro-N-methyl-1-butanamine


  • aromatic amine aniline

N-methylaniline

(N-_____benzenamine)

aniline

(benzenamine)

p-bromoaniline

(4-_____benzenamine)


H-bond

H-bond

amide

H-bond

H-bond ..

amine

H-bond

9.3


137 oC

  • ?

  • .............................................................................................................................

    .............................................................................................................................

104 oC

67 oC


    • ___________

    • aromatic amine __________

    • ?

    • ___________________


1) A B

2) ()

B

A

C

A

B


9.4

9.4.1 (acidity and basicity)

  • - N EN O

    • ________(20 )

    • ________ N ___________O

amine

ammonium ion


    • lone pair electrons N ____________________

    • lone pair electrons _______________________


ammonium salt

+

H2SO4

H

HSO4

-

morphine sulfate

___________

morphine

____________

9.4.2

  • _____________ _____________________________


  • (Morphine) ______________

  • aspirin 50

  • _______________

esterification ?


9.4.3

Acid chloride

amine

amide

  • _______________ (peptide linkage) __________ _________________ (amino acid)

  • ______________


(amino acid)

amino carboxyl

______

group

_______

group


amide ammonium salt

amide amine (ammonia)

9.4.4

  • _________ ()

  • ____________


aspartic acid

phenylalanine

(Aspartame) () 160 2

__________________________________

_________________


9.5 1o 2o 3o

9.5.1 Hinsbergs test

1o amine

benzene sulfonamide

benzene sulfonyl chloride

2o amine

benzene sulfonamide

benzene sulfonyl chloride

3o amine_______________


1o aliphatic

amine

2oamine N-nitrosamine

9.5.2 aliphatic amine (HNO2)

  • (HNO2) HCl (NaNO2)

3o amine_______________


1-Amines + HNO2 (cold soln)

2-Amines + HNO2 (cold soln)

3-Amines + HNO2 (cold soln)

aliphatic amine

____________________

_____________________

(N-nitrosoamine)

_____________________

()


N-nitrosamine ____________

_________

2o ____________


(diazotization)

benzene

diazonium chloride

aniline

___________

____________

9.5.3 (diazotization) aromatic amine

  • 1o (benzene diazonium chloride)


azo

azo

_____________________ (coupling reaction) _____________________ azo

?

benzene

diazonium chloride

aniline

benzene

diazonium chloride


__________ azo dye

Sudan I (____)

Methyl orange

azo


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