Reactions of Carboxylic Acids
In this problem we shall consider four carboxylic acid reactants:
    butanoic acid         benzoic acid     cyclopentanecarboxylic acid     2,2-dimethyl propanoic acid    

These compounds may be reacted with nine different reagents:
LiAlH4 in ether
(aqueous acid workup)
SOCl2 & heat
(or PCl3 & heat)
acid catalyst , heat (–H2O)
in ether
(i) NaOH (1 equiv.)
(ii) C6H5CH2Br
Br2 & heat
PBr3 catalyst
(i) CH2N2 in ether
    (ii) 2 CH3MgBr in ether
(i) SOCl2 & heat
    (ii) 2 C6H5NH2 (aniline)
(i) SOCl2 & heat
    (ii) p-xylene & AlCl3 + heat

Select one carboxylic acid from the first group,
and one reagent from the second group.
To practice using the drawing program Click Here  
To review the chemistry of carboxylic acids Click Here