Organic Chemistry

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CH3-NH2

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methylamine
(methanamine)

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CH3-CH-CH2-NH2
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CH3

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isobutylamine
(2-methyl-1-propanamine)

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(C2H5)3N

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triethylamine
(N,N-diethyl-ethanamine)

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CH3-CH2-CH2-N-CH3
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C2H5

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ethylmethylpropylamine
(N-ethyl-N-methyl-1-propanamine)

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Cl-CH2-CH2-NH2

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2-chloro-ethylamine
(2-chloro-ethanamine)

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pKas of NH3 CH3NH2 CH3CH2NH2 CH3CH2CH2NH2

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9.26 10.64 10.75 10.67

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basicity of NH3, 1°, 2°, 3°

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2° > 1° > 3° > NH3
3° amines are less basic BC of steric hindrance

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name

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aniline

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which is more basic?
aniline + electron donating
vs
aniline + electron withdrawing

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electron donating (-CH3, -NH2, -OCH3) will increase reactivity of the ring and make it more basic compared to electronic withdrawing (-NO2, -Cl, -CN)

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CH3CH2CH2-NH2 + CH3-Br -> ?

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R-NH-R' (2° amine)

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Gabriel synthesis

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Friedel Crafts Alkylation

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BENZENE-C(CH3)3

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Friedel Crafts Alkylation Limitations

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1. only alkyl halides work. not aryl or vinyl (double bond) halides
2. No rxn w e- withdrawing groups (-NO2, -CN, -SO3H, -HC=O, -COOH)
3. Multiple substitutions might occur
4. carbocation rearrangements might occur , esp with 1° alkyl halides

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Friedel Crafts Acylation Limitations

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1. Multiple substitutions DO NOT occur
2. carbocation rearrangements DO NOT occur
3. No rxn with strong e- withdrawing groups
4. acid anhyrides can be used instead of acyl

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Canizzaro Reaction

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benzaldehye is attacked by base (-OH) and one benzoic acid (carboxylic acid) and one benzyl alcohol is formed

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2 benzaldehyes without an alpha H

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