the solution

Organic compounds that break up into 2 organic moieties on hydrolysis are the esters- therefore compounds B and C are carboxylic acid and alcohol. When B reacted with thionyl chloride, two chlorines were substituted in, so aside from the carboxylic acid group there must have been an alcohol group - i.e. it was either 2-hydroxy or 3-hydroxy propanoic acid. It had to be the 3 hydroxy as 2- hydroxypropanoic acid contins a chiral carbon and therefore would rotate the plane of polarized light( unless it happened to be a 50:50 racemic mixture!)
Compound C ( which is an alcohol) produces oxalic acid( ethandioic acid) on complete oxidation so must have been a 1,2 diol, i.e. ethan-1,2,diol.
The ester of these rwo would be 2hydroxyethyl,(3hydroxy)propanoate-compound C

The last time I went home

I am originally from Ireland and for reasons that I wont go into I seldom go home. I got a phone-call from the brother-in-law. " Are ya comin' home to sat goodbye to your mother, or are ya comin' home to bury her- 'cos she is on her way." " Be there soon", says I.

Arranging travel from NZ to Ireland is difficult at the best times, so over Christmas I finally managed to organise a flight via Tokyo and Franfurt- 1/2 way round the world!
When I went into the duty free in Auckland airport, I saw Irish whisky on special at only $20NZ a bottle- not knowing what the quota was in Dublin I bought half a dozen.
The flights to Tokyo then Frankfurt were long and boring, consuming 3 books and none of the whisky(I was saving that for whatever faced me in Dublin). As I boarded the Aer Lingus flight from Frankfurt to Dublin, there were two types of passengers- a single transit passenger from NZ- and the whole of the Irish symphony orchestra! It was a fun journey as these talented musicians played amusing musical games. On landing in Dublin airport, the whole orchestra, baggage and all disappeared through the VIP entrance and I was left to face the whole of the customs alone.
" Have you anything to declare?" Customs officers in Ireland are like Russian police, big beefy and frightening.
" Er, well I have these six bottles of Irish that I got in Auckland- I'm sorry officer sir but I didn't know the quota(I hate it when I'm reduced to a snivelling grovelling sycophant)
" What the fuck are you doin', bringing Irish whisky into Ireland ya stupid eejit"
" Well officer sir, it only cost about 4 pounds a bottle in Auckland>"
" 4 pounds a bottle??!! Holy mother of Jesus - hey lads lets hire a plane!!!
With that I gratefully slunk away with my booty. I got to say goodbye to mammy and we gave her a good wake with 6 bottles of Irish making a small contribution to prosceedings.
Go mbeirimid beo ar an am seo aris!

Organic Chemistry

I put this question in before and then made a mess of it so here goes for a repeat.
A compound C5H10O4(A) which does not rotate the plane of polarized light is subjected to acid hydrolysis and produces two compounds C3H6O3(B) and C2H6O2(C). All three compounds react with thionyl chloride (A) producing C5H8O2Cl2, (B) producing C3H4OCl2, and (C) producing C2H4Cl2. On oxidation with acidified dichromate, (A) produces C5H6O5 which does not react with Tollen's Reagent, (B) produces C3H4O4 and (C) produces oxalic acid.
Identify the structural formulae and names of A B and C
Answer later- or if you can, post your solution in comments
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Kiwiman

Author:Kiwiman
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