Organic Solutes in Aqueous Solutions

B29

B30

Cyclohexanone

Stadlbauer, J.M., Venkatesvaran, K. and Walker, D.C.

Can. J. Chem., 1997, 75, 74.

Reaction: C-(CH2)5C=O + Mu ® C-(CH2)5COMu

Type of reaction: addition to C=O  bond with Mu attached to O atom

kM = (1.17 ± 0.2) x 108 dm3mol-1s-1    at pH = 6-7

kH – unknown for cyclohexanone but determined for cyclopentanone:

kH = (4.91
± 0.28) x 107 dm3mol-1s-1

Mezyk, S.P., Lossack, A. and Bartels, D.M. Can. J. Chem., 1997, 75, 1114.

assuming similar values of kH for cyclopentanone and cyclohexanone one obtains

KIE = kM / kH = 1.2 x 108 / 4.9 x 107 » 2.5

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