Evidence Compound H is neutral to litmus. Compound H is soluble in water.

H formed I when reflux with acidified K2Cr2O7. I forms a diester when warmed with 2 moles of ethanol and concentrated sulfuric acid. J reacts with Br2(aq) form to H.

Conclusion Compound H should not have any acidic group (e.g. COOH) or basic group (e.g. NH2). Compound H contains alcohol group. (soluble via hydrogen bonding with water) Increase in 2 oxygen atoms. H contains 2 primary alcohol that is oxidised to carboxylic acid. (from evidence below) Compound I contains 2 carboxylic acid. J contain 1 alkene group. Gain in one Br atom, one H and O atom. Br and OH atom added to the C=C Decrease in 2 carbon atoms (from H to J). Compound H cannot have two since it only has one C=C group. Therefore ethanedioic acid must be formed which break down further to form 2CO2 (lost of 2 carbon atoms therefore).

Compound H is oxidised by hot acidified KMnO4 to compound M. Only ONE organic compound (with 3 carbons) is formed.

Synthesis pathway for compound M:

KCN LiAlH4, ether CHOCH2Cl reflux ethanol 2. Cr2O72-/H+, relux 1. H+(aq),Heat

[reduction] [reduction]

K [reduction]

[nucleophilic substitution]

L [reduction]

1. acid hydrolysis
2. oxidation

M [reduction]

Determining the alkene structure/Compound H: One side of the alkene chain must have 3 carbons and the other side 2 carbons. The side with 3 carbons will form M while the other side with 2 carbons forms ethanedioic acid. From the deduction above, H contains 2 primary alcohol groups and no carboxylic acid. To form M the alkene chain must have:
Overall, structure of compound H is:

To form ethanedioic acid the alkene chain must have:

Compound I
K2Cr2O7/H+ reflux [Oxidation]

Br2 (aq) [Electrophilic addition] Compound J

Compound H hot acidified KMnO4 [Oxidation]

Compound M