Question

Alcohols undergo an oxidation when treated with Dess-Martin periodinane in dichloromethane. The product of the above reaction has the following spectroscopic properties; propose a structure. MS: M^+ = 86 IR: 1715 cm^-1^1 H NMR: 0.90 delta (3H, triplet); 1.68 6 (2H, multiplet): 2.13 delta (3H, singlet); 2.40 delta (2H, triplet)^13 C NMR: 13.6, 16.6, 29.8, 47.0, 207.7 delta

Answer 1

Molecular weight= 86, M⁺=86

IR: 1715cm^-1 from carbonyl group

¹HNMR: 2.13 from CH₃ Closer to carbonyl group

2.40 CH₂ next to carbonyl group

1.68 from the another CH₂

0.90 from CH₃ farthest to carbonyl group

¹³CNMR: five different carbons, 207.7 from carbon bonded to oxygen