Question

Please answer the following:

(a) An optically inactive compound A (C6H10O4) can be resolved into enantiomers and has the following NMR spectra: 13CNMR: δ 13.5, δ 41.2, δ 177.9 1H NMR: δ 1.13 (6H, d, J=7Hz); δ 2.65 (2H, quartet, J=7Hz); δ 9.9 (2H, broad, s, disappears after D2O shake) Draw either enantiomer; use wedge/dash bonds, including for any H on a chirality center.

(b) Give the structure for an isomer of compound A that has a melting point that is appreciably different from that of A yet NMR spectra that are almost identical to those of A. Use wedge/dash bonds, including for any H on a chriality center.

Thank you!

Answer 1