1) Compound A (C18H18O4) was boiled with aqueous sodium hydroxide
solution and a high boiling liquid B was obtained by distillation of
the alkaline solution.  Acidification of the residue gave a
precipitate of compound C (C8H8O2) which,when heated on a crucible
lid, burn a smoky flame.  When C was treated with thionyl chloride or
phosporous trichloride, compound D was produced, and this, with
ammonia, gave compound E (C8H9NO).  Compound E was heated with bromine
and sodium hydroxide to give compound F(C7H9N); when this was treated
in the cold with sodium nitrate and an excess of dilute hydrochloric
acid a colorless gas was evolved and when the resulting liquid
reaction mixture was added to an alkaline solution of phenol the
mixture remained virtually colorless.  After purification, the high
boiling liquid B was found to have vapor density of 31.  Combustion of
.020g of B gave .0284g of carbon dioxide and .0174g of water. 
Oxidation with warm aqueous alkaline potassium permanganate readily 
gave oxalate ion.  Identify compounds A-F and write equations for the
reactions involved?

2.  Using the malonic ester show how the following can be synthesized
a) 3-Phenylpropanoic acid
b) Ethyl cyclobutane carboxylate

Here's the start

Cheers
Brian


<< 1) Compound A (C18H18O4) was boiled with aqueous sodium hydroxide
solution and a high boiling liquid B was obtained by distillation of the
alkaline solution. >>

OK, The formula of A could be almost anything but the product is
obviously a sodium salt. My first guess is that A is an ester that we
are saponifying.

<< Acidification of the residue gave a precipitate of compound C
(C8H8O2) which,when heated on a crucible lid, burn a smoky flame. >>

This would mean that C is a fatty acid. The formula and the smokey flame
clearly indicate a large degree of unsaturation. So we've narrowed C
down to C7H7COOH. B was C7H7COONa.

<< When C was treated with thionyl chloride or phosporous trichloride,
compound D was produced, >>

D is an acid chloride. So D is C7H7COCl.

<< and this, with ammonia, gave compound E (C8H9NO). >>

E is an amide. So E is C7H7CONH2.

<< Compound E was heated with bromine and sodium hydroxide to give
compound F(C7H9N); >>

F is a primary amine and is C7H7NH2.

<< when this was treated in the cold with sodium nitrate and an excess
of dilute hydrochloric acid a colorless gas was evolved >>

This is a test for primary amines and the evolved gas is nitrogen. The
reaction is C7H7NH2 + HNO2 --> C7H7OH + N2 + H2O. However it isn't as
simple as this and a mix of alcohols would be the result if the C7H7
group permitted it.

<< and when the resulting liquid reaction mixture was added to an
alkaline solution of phenol the mixture remained virtually colorless.
After purification, the high boiling liquid B was found to have vapor
density of 31. Combustion of .020g of B gave .0284g of carbon dioxide
and .0174g of water. Oxidation with warm aqueous alkaline potassium
permanganate readily gave oxalate ion. >>

I can't remember what this is telling us. My guess is that it is somehow
narrowing down the nature of the C7H7 group. The obvious structure that
fits C7H7 is a benzyl group.