23 Chapter Amines

1) Alkyl Halide + NH3 (excess)

2) Alkyl Halide + R-NH2 (excess)

3) Alkyl Halide + R2-NH (excess)

4) Alkyl Halide + R3-N (excess)

1) 1° Amine (Substitution then Deprotonation)

2) 2° Amine (Substitution then Deprotonation)

3) 3° Amine (Substitution then Deprotonation)

4) Quarternary Ammonium Salt (N/A)

SN2

5) Alkyl Halide (excess) + ANY Amines

Quarternary Ammonium Salt

SN2

-wont stop until it reaches Quarternary Ammonium Salt

6) Gabriel Synthesis

Pthalimide → R-NH2 + PhthalimideCOO-

Reductive Methods

1) Reagents

H2, Pd-C

OR

Fe, HCl

OR

Sn, HCl

NO2 → NH2

2) Reagent:

1) LiAlH4

2) H2O

CN → 1° Amine: NH2

3) Reagent:

1) LiAlH4

2) H2O

1° Amide → 1° Amine

2° Amide → 1° Amine

3° Amide → 1° Amine

GETS RID OF C DOUBLE BOND O by adding H’s

Reductive Amination

1) Reagent

NH3, R-NH2, R2-NH

AND mild Acid, NaBH3CN

NH3 → 1° Reduced Amine

R-NH2 → 2° Reduced Amine

R2-NH → 3° Reduced Amine