Chemistry Homework Solutions
Problem
#44632

Indentify unknown organic liquids

An unknown organic liquid A, was found to burn with a yellow, sooty flame and give positive Lucas test (about 5 minutes). Upon treatment with sodium dichromate-sulfuric solution it produced compound B which also burned with a yellow sooty flame. Compound B gave a positive 2,4-dinitrophenylhydrazine test, but a negative result when treated with Tollens reagent. However, B did give a positive iodoform test. The H NMR spectrum for compound A showed the following:

1.4 ppm   3H (doublet)
1.9 ppm   1H (singlet)
4.8 ppm   1H (quartet)
7.2 ppm   5H (complex multiplet)

Give the structures and suitable names for compounds A and B.

Thanks

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