An Organic compound, A, has an empirical formula C3H6O and a molar mass of between 100 and 125. NMW spectroscopy indicates the presence of four methyl groups.
The compound A was reacted with sodium hydroxide. After the reaction the excess sodium hydroxide was neutralised and two products B and C were isolated.
B was acidic whereas C was neutral. Neither B or C could be oxidised. Both B and C were soluble in water. Both B and C reacted with sodium
a.) Determine the molecular formula of A
b.) Identify the functional group in A
c.) Identify(with semi structural formula) B,C and hence A
d.) State why C could not be oxidised.
e.) Write balanced equations for the reactions of B and C with sodium.
a) The MW of the empirical formula is 58, so the real compound has a double MW than the starting formula. "A" formula, so, is C
6H
12O
2.
b) Considering that "A" compound reacts in base, I strongly suggest an esther group as the only functional group, given the formula.
c) Given the other informations, I can assess the following structures:
A: 2,2-dimethylethanoil acetate.
B: Acetic acid.
C: t-butyl alcohol.
d) C cannot be oxidized because he has no idrogens in the carbon atom near the hydroxyl group.
e.1) C
2H
4O
2 + Na
C
2H
3O
2Na + 1/2 H
2.
e.2) C
4H
10O + Na
C
4H
9ONa + 1/2 H
2.
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