Question

Give the structure that corresponds to the following molecular formula and NMR spectra: C6H14O 1H NMR: ? 0.91 (6H, d, J = 7 Hz); ? 1.17 (6H, s); ? 1.48 (1H, s; disappears after D2O shake); ? 1.65 (1H, septet, J = 7 Hz). 13C NMR: ? 17.6, ? 26.5, ? 38.7, ? 73.2.

Answer 1

Answer 2

Most likely is 2,3-dimethyl-2-butanol. Here's how I figured that out:

? 0.91 (6H, d, J = 7 Hz)
The CH3 groups in an isopropyl group CH3)2CH-

? 1.17 (6H, s)
The CH3 groups in a substituted isopropyl group CH3)2CX- (X ? H)

? 1.48 (1H, s; disappears after D2O shake)
-OH group
This is a prime candidate for the X substituent above, (CH3)2C-OH

? 1.65 (1H, septet, J = 7 Hz)
The methine proton in the isopropyl group (Me)2CH-

Combine the two groups:

(CH3)2CH-C(OH)(CH3)2

Answer 3

[REMOVED]