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17 Nov 2019
An unknown compound, A, was isolated from the bark of a conifer tree growing in northern British Columbia. This compound, C_8H_14, was found to be optically active because of two stereo genic carbon atoms. When it was hydrogenated with a platinum catalyst, compound B (C_8H_16) was formed. Hot, basic permanganate solution oxide/ed A to two different compounds: C (CH_2O_2) and D (C_7H_12O). Compound C was not optically active and had a very strong and broad IR absorption centred around 3000 cm and a strong medium width JR absorption centred at 1750 cm^-1. Compound D had a strong IR absorption at 1730 cm^-1. It was still optically active, with two stereo genic carbon atoms. Deduce possible structures for compounds A, B, C, and D. Give the reasons for your choices. Note that there may be more than one correct answer for A, B, and D.
An unknown compound, A, was isolated from the bark of a conifer tree growing in northern British Columbia. This compound, C_8H_14, was found to be optically active because of two stereo genic carbon atoms. When it was hydrogenated with a platinum catalyst, compound B (C_8H_16) was formed. Hot, basic permanganate solution oxide/ed A to two different compounds: C (CH_2O_2) and D (C_7H_12O). Compound C was not optically active and had a very strong and broad IR absorption centred around 3000 cm and a strong medium width JR absorption centred at 1750 cm^-1. Compound D had a strong IR absorption at 1730 cm^-1. It was still optically active, with two stereo genic carbon atoms. Deduce possible structures for compounds A, B, C, and D. Give the reasons for your choices. Note that there may be more than one correct answer for A, B, and D.
Nelly StrackeLv2
29 Jun 2019