The reaction illustrated by the equation below is a very general one that can be catalyzed by acid, base, and some enzymes. It therefore needs to be taken into consideration when planning syntheses that involve esters of polyhydroxy substances like glycerol and sugars:

Spectral data for F:
MS (m/z): (after trimethylsilylation): 546, 531
IR (cm-1): 3200 (broad), 1710
1H NMR (δ) (after exchange with D2O): 4.2 (d), 3.9 (m), 3.7 (d), 2.2 (t), and others in the range 1.7 to 1
13C NMR (δ): 172 (C), 74 (CH), 70 (CH2), 67 (CH2), 39 (CH2), and others in the range 32 to 14
(a) What is the structure of product F?
(b) The reaction is intramolecular. Write a mechanism by which it probably occurs.

Transcribed Image Text:

trace HCIO 10 min., room temp. 90% yield CH2CHa 14