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)		 CH3CH2OH
acid catalyst , heat (-H2O)
CH2N2
in ether		 (i) NaOH (1 equiv.)
(ii) benzyl bromide		 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 review the chemistry of carboxylic acids Click Here.