Organic compound A is chiral and contains only three elements with the molecular weight (MW) of 149 — Organic Chemistry Chemistry Question
Into the Unknown
Organic compound A is chiral and contains only three elements with the molecular weight (MW) of 149 (rounded to an integer).
1H NMR spectrum of compound A shows among others, three types of aromatic protons, and its 13C NMR spectrum shows eight signals, of which four signals are in the range of 120-140 ppm.
Compound A can be prepared by treating a carbonyl compound with methylamine followed by NaBH3CN.
Write all possible structural formulae of compound A. No stereochemistry is required, and do not include stereoisomers.
One of the position isomers of compound A (structure A1, A2 or A3) can be synthesized from compound B or C and D as shown in the diagram below. Write down the structural formulae of compounds B-F, and the position isomer of compound A.
Compound A is the (R)-form of one of structures A1– A3. It can be prepared from vicinal diols X and Y as shown in the diagram below. Both diols are structural isomers, and each structure contains one carbon less than that of compound A. Write down the structural formulae of compounds G-N, X, Y and the (R)-form of compound A. You must show stereochemistry of all compounds.