This document provides guidance on various chemical reaction routes and reagents for converting functional groups. It recommends using LiAlH4 in ether for the direct conversion of a nitrile to an aldehyde. For a short route to convert a nitrile to an amide, it suggests NaNH2/Liq. NH3. It advises against using a-halogenation due to special precaution and reaction conditions required, and notes mixed aldol products would form. It recommends LiI in moist DMSO for elimination of an ester group.

1. (Work-up)

3. LiAlH4
Ether
/
Find out the reagent for direct
conversion of -CN to -CHO
1. MeMgBr
2. H3O+
Short route

4. 3. H2O
Work-up

7. NaNH2/Liq. NH3
Base

14. Reactive functional gr.

16. Retro-Birch
Retro-

17. Hg2+, CdCO3,
H2O

19. a-Helogenation

20. Go through enamine of silyl enol ether
method

24. Dont go through this path
because this path requires
special precaution and special
reaction condition, and also
costly.
Mixed aldol products
will be formed.
Use LiI, moist DMSO
for elimination of
ester group
LiI, Moist
DMSO

25. Write solvent
and Temp.

29. partial hydrolysis
30% H2O2 / K2CO3 /
DMSO at 0 oC

31. CrO3, H2SO4,
H2O, Acetone

33. Use PCC, PDC
or Swern oxidation
method or Jones
reagent

34. NaOEt/EtOH