for-each-pair-of-compounds-determine-which-of-the-two-compounds-has-a-higher-wat

Question

For each pair of compounds, determine which of the two compounds has a higher water solubility. Give a brief explanation for your choice.
(i) pentan-1-ol or cyclopentanol
(ii) hexan-1-ol or phenol
(iii) 3-ethylpentan-3-ol or heptan-2-ol
(iv) pentan-2-ol or cyclopentane-1,3-diol
(v)

Chemical structures of two compounds labeled A and B, showing hydroxyl groups for comparison.

Accepted Answer

(i) cyclopentanol, because it has a more compact structure.
(ii) phenol, because it has a more compact structure.
(iii) 3-ethylpentan-3-ol, because it has a branched structure.
(iv) cyclopentane-1,3-diol, because it has more hydroxyl groups.
(v) Both compounds have identical solubility because they are identical.

Answer

(i) cyclopentanol, because it has a higher molar mass.
(ii) phenol, because it has a more compact structure.
(iii) 3-heptan-2-ol because it has a branched structure.
(iv) cyclopentane-1,3-diol, because it has more hydroxyl groups.
(v) Both compounds have identical solubility because they are diastereomers.

Answer

(i) pentan-1-ol, because it has a more compact structure.
(ii) phenol, because it has a more compact structure.
(iii) heptan-2-ol, because it is a secondary alcohol.
(iv) cyclopentane-1,3-diol, because it has more hydroxyl groups.
(v) Both compounds have identical solubility because they are enantiomers.

Answer

(i) pentan-1-ol, because it has a linear structure.
(ii) phenol, because it has a more compact structure.
(iii) heptan-2-ol, because it has more hydroxyl groups.
(iv) cyclopentane-1,3-diol, because it has more hydroxyl groups.
(v) Both compounds have identical solubility because they are diastereomers.

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