Problem: Structure and solubilitySuppose the hydrogens on the OH groups in glucose (refer the figure) were replaced with methyl groups, CH3.Would you expect the water solubility of the resulting molecule to be higher than, lower than, or about the same as the solubility of glucose?

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Cyclohexane, C6H12, which has no polar OH groups, is essentially insoluble in water. Cyclohexane is a six-membered ring with carbon as all of its vertices. Each carbon is also single bonded out of the ring to two H atoms. Glucose is also a six-membered ring, but it has carbon at five of its vertices and O as the final vertex. Attached to the ring are five OH groups, which are hydrogen-bonding sites. In glucose, the OH groups enhance the aqueous solubility because of their ability to hydrogen bond with H2O.


Structure and solubility


Suppose the hydrogens on the OH groups in glucose (refer the figure) were replaced with methyl groups, CH3.


Would you expect the water solubility of the resulting molecule to be higher than, lower than, or about the same as the solubility of glucose?

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