Predict which member of each pair is more soluble in water. Explain your prediction.

(a)

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Hydrogen bonding

molecules containing a hydrogen atom linked by a covalent bond to a highly electronegative atom (like N,O of F). It is of two types namely, intermolecular hydrogen bonding (formed between two molecules of the same or different compounds) and intramolecular hydrogen bonding (formed between hydrogen atom and N,O of F atom of the same molecule).

02

Identification of compounds more soluble in water

The presence of hydrogen bonding between molecules of a substance tells us that the molecules are polar. This implies that the molecules will be soluble in a polar solvent like water. But if the hydrophobic part of the molecule is big, then that molecule would not be soluble in water. Again, if some compounds have extremely polar bonds, then they will be soluble in water.

03

Predicting the more soluble compound

  1. The second compound will be more soluble in water because it can form hydrogen bonds with water.
  2. The second compound will be more soluble in water because it can form more hydrogen bonds with water. The second compound has two oxygen atoms while the first compound has only one oxygen atom.

  3. The first compound is more soluble in water since it has a shorter carbon chain which is hydrophobic.

  4. The second compound will be more soluble in water because it can form hydrogen bonds with water.

  5. The second compound will be more soluble in water because it can form more hydrogen bonds with water. The second compound has two bromine atoms while the first compound has only one oxygen atom.

  6. The second compound is more soluble in water since it has a shorter carbon chain which is hydrophobic.

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Most popular questions from this chapter

Compare the relative acidity of 1-molar aqueous solutions of the following acids.

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Ethyllithium is often used as a base in organic reactions,

(a)Predict the products of the following acid-base reaction,

CH3OH + CH3CH2Li

(b) What is the conjugate acid ofCH3CH2Li ? Would you expectCH3CH2Li to be a strong base or a weak base?

Question: The pKa of ascorbic acid (vitamin C, page 9) is 4.17 , showing that it is lightly more acidic than acetic acid (CH3COOH, pKa = 4.74).

(a)Show four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.

(b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.

(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group

Dimethyl ether and ethanol are isomers. Their boiling points are very different, however. Explain why these two compounds have dramatically different boiling points.

CH3-O-CH3 CH3CH2-OH

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