Hydrophobic Effect Lab Report

536 Words2 Pages

Hydrophobic rate acceleration. Breslow and his co-workers first explored the effect of water on the rate of Diels-Alder reactions in a quantitative manner3. This was done by comparing the rates of reaction in Figure 2 in isooctane, methanol and water. It was found that all three reactions proceeded significantly faster in water than in nonpolar organic solvent. Solvent polarity effect was not the reason for the enhancement of the reaction. It was found that the reaction between 1.1 (cyclopentadiene) and 1.2 (acrylonitrile) was only slightly faster than isooctane. The reaction between 1.8 (9-hydroxymethylanthracene) and 1.9 (N-ethylmaleimide) was found to be slower in methanol than the isooctane due to the disrupted hydrogen-bonded association of the diene and dienophile. This was a good evidence that there are other factors affecting the reaction in water. The evidence of a hydrophobic effect involved from a series of experiments that measured rates of reactions in the presence of additives known to increase or decrease hydrophobic effect1. Agents such as lithium chloride (LiCl), prohydrophobic, causes the free water molecules to collapse around its ions, acting as an internal pressure which increases the reaction rate with negative activation volume1,3. Enforced hydrophobic interactions. …show more content…

This is a result of a more favorable entropy contribution, due to the reduction of apolar molecular surface area during the activation process4. The substituent of the reaction does affect the rate enhance but depended on the compounds being used. The Gibbs energy transfer plot of the reaction of compounds 1.1 and 1.5 from figure 1, reveals that the rate acceleration in water relative to the alcohol was due to the destabilization of the initial state. The stabilization of the transition state relative to the initial step was proposed to be a consequence of the reduction of hydrophobic surface

Open Document