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Chapter 3: Q.64. (page 91)

Question: Explain why A is less water soluble than B, even though both compounds have the same functional groups.

Short Answer

Expert verified

Answer

The reason why A is less water-soluble than B is due to the intramolecular hydrogen bonding.

Step by step solution

01

Factors affecting solubility

The solubility of a compound in water gets altered due to the bonding of the molecules with the same molecular formula.

The intramolecular hydrogen bonding does not let the compound undergo the formation of hydrogen bonds with the water molecules. Therefore, the solubility increases with the increase in the intermolecular hydrogen bonding as it forms hydrogen bonds with water molecules.

02

Explanation

Ortho benzaldehyde (A) has intramolecular hydrogen bonding between the aldehyde’s oxygen and the acidic hydrogen of the OH group. Therefore, the compound is less eligible to form hydrogen bonding with the water molecules.

Therefore, the solubility is low.

Meta benzaldehyde (B) has intermolecular hydrogen bonding between the aldehyde’s oxygen and the water molecules and acidic hydrogen of the OH group. Therefore, the compound is more eligible to form hydrogen bonding with the water molecules.

Therefore, the solubility is high.

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Most popular questions from this chapter

Question: Draw the structure of a compound of molecular formula C4H11NOthat fits each description: a. a compound that contains a 10amine and a 30alcohol; b. a compound that contains a 30 amine and a 10alcohol.

Question: Which of the following structures represent soaps? Explain your answers.

a.

b.

c.

Question: Today, synthetic detergents like the compound drawn here, not soaps, are used to clean clothes. Explain how this detergent cleans away dirt.

Question: a. Identify the functional groups in the ball-and-stick model of neral, a compound with a lemony odor isolated from lemon grass.

b. Draw a skeletal structure of a constitutional isomer of neral that should be more water soluble.

c. Label the most electrophilic carbon atom.

Question: Poly(ethylene glycol) (PEG) and poly(vinyl chloride) (PVC) are examples of polymers, large organic molecules composed of repeating smaller units covalently bonded together. Polymers have very different properties depending (in part) on their functional groups. Discuss the water solubility of each polymer and suggest why PEG is used in shampoos, whereas PVC is used to make garden hoses and pipes. Synthetic polymers are discussed in detail in Chapters 15 and 30.
See all solutions

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