Does stearic acid soluble in ether or NaOH? why?

Identifying the unkown through test results?

• unknown substance A gave the following test results in lab: •Br2/dark and CHCl3/AlCl3 tests were negative but Br2/light was positive and gave an acidic Litmus test; • the compound was partially water-soluble and soluble in all organic solvents tested; • the product could not be extracted into alkaline water from an ether solution; • the test with 2,4-dinitrophenylhydrazine failed; • the Lucas reagent gave a moderately fast reaction; •the CrO3/H2SO4 test was positive, but the product could not be extracted into alkaline water; •the I2/NaOH test was positive; after partitioning the product between water and ether, the aqueous phase was acidified and extracted with fresh ether, and the ether layer was distilled to give a liquid with a strong vinagry smell boiling at the same boiling point as propanoic acid; • the sodium test produced copious amounts of bubbling (the gas was identified as H2 by a flame test). Use these results to infer the structure of compound A.

• Answer:

  From the positive tests: (Lucas) A is an alcohol ("Chromic Acid") A is a primary or secondary alcohol ("Iodoform" Test) A contains a CH3-CH(OH)- fragment. After loss of CHI3 (the terminal methyl group), extraction and acidification propanoic acid remains. So A must have been butan-2-ol CH3-CH(OH)-CH2-CH3 Additional: In presence of light bromine would subsitute hydrogens from main carbon chain, also producing HBr (the acidic gas)