5. The behaviour A and B below, on treatment with NaOAc/HOAc, show that A is hydrolysed 13 times faster than B. Kinetic studies show A is racemised under the conditions and a single product forms, while B gives a mixture of products with cis-C being the kinetic product. Account for these reaction outcomes by drawing "3 dimensional" pictures of the reacting conformations, and including the relevant orbitals. TSO A single enantiomer racemic NaOAc / ACOH ACO H B OTS NaOAc / AcOH H O OH cis - kinetically

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5. The behaviour A and B below, on treatment with NaOAc/HOAc, show that A is hydrolysed
13 times faster than B. Kinetic studies show A is racemised under the conditions and a
single product forms, while B gives a mixture of products with cis-C being the kinetic
product.
Account for these reaction outcomes by drawing "3 dimensional" pictures of the reacting
conformations, and including the relevant orbitals.
TSO
A
H
single enantiomer
racemic
NaOAc
/AcOH
ACO
H
B
OTS
NaOAc
/ AcOH
H
O
OH
cis - kinetically
Transcribed Image Text:5. The behaviour A and B below, on treatment with NaOAc/HOAc, show that A is hydrolysed 13 times faster than B. Kinetic studies show A is racemised under the conditions and a single product forms, while B gives a mixture of products with cis-C being the kinetic product. Account for these reaction outcomes by drawing "3 dimensional" pictures of the reacting conformations, and including the relevant orbitals. TSO A H single enantiomer racemic NaOAc /AcOH ACO H B OTS NaOAc / AcOH H O OH cis - kinetically
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