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Preparation of Amines

Five amine syntheses are outlined below. In each reaction box enter a single letter designating the best reagent and conditions selected from the list at the bottom of the page.
Skeletal structure of (bromomethyl)cyclohexane, cyclohexane ring bearing a CH2Br group

1.

First Step
reaction arrow
Second Step 		Skeletal structure of 2-cyclohexylethylamine, cyclohexane ring with a CH2CH2NH2 chain

Skeletal structure of benzaldehyde, benzene ring bearing a CHO group

2.


First Step
reaction arrow
Second Step
Third Step 		Skeletal structure of N-benzyl-N-ethylacetamide, amide of benzyl and ethyl groups on nitrogen

Skeletal structure of piperidine, six-membered ring with one NH

3.

First Step
reaction arrow
Second Step 		Skeletal structure of N-cyclohexylpiperidine, piperidine N bonded to a cyclohexyl ring

Skeletal structure of nitrobenzene, benzene ring bearing an NO2 group

4.

First Step
reaction arrow
Second Step 		Skeletal structure of N,N-dimethylaniline, benzene ring with an N(CH3)2 group

Skeletal structure of isobutyl bromide, 1-bromo-2-methylpropane

5.


First Step
Second Step
reaction arrow
Third Step
Fourth Step 		Skeletal structure of N-isobutylcyclohexylamine, cyclohexyl-NH-CH2CH(CH3)2 secondary amine

A. (i) LiAlH4 in ether
(ii) H2O & base		 B. C2H5NH2 (cat. H(+)) C. NaCN in alcohol D. H2 & Ni catalyst
or H2 & Pd catalyst		 E. NaN3 in alcohol
F. (CH3CO)2O & pyridine G. C2H5Br H. cyclohexanone (cat. H(+)) I. 2 CH3I & pyridine J. KOH in H2O

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