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Chapter 21: Problem 67

Hydroxyl radicals can pluck hydrogen atoms from molecules ("hydrogen abstraction"), and hydroxide ions can pluck protons from molecules (“deprotonation”). Write the reaction equations and Lewis dot structures for the hydrogen abstraction and deprotonation reactions for the generic carboxylic acid R-COOH with hydroxyl radical and hydroxide ion, respectively. Why is hydroxyl radical more toxic to living systems than hydroxide ion?

Short Answer

Expert verified
The hydrogen abstraction reaction for the carboxylic acid R-COOH with hydroxyl radical (OH•) can be represented as: R-COOH + OH• → R-COO• + H2O. The deprotonation reaction for the carboxylic acid R-COOH with hydroxide ion (OH-) can be represented as: R-COOH + OH- → R-COO- + H2O. Hydroxyl radicals (OH•) are more toxic to living systems than hydroxide ions (OH-) because they are highly reactive and can cause oxidative stress in cells, leading to damage or death.

Step by step solution

01

Write the hydrogen abstraction reaction equation

The hydrogen abstraction reaction for the carboxylic acid can be written as follows: R-COOH + OH• → R-COO• + H2O Here, OH• is the hydroxyl radical and R-COOH is the given carboxylic acid.
02

Draw the Lewis dot structures for the hydrogen abstraction

The Lewis dot structures for the reactants and products in the hydrogen abstraction reaction are: Reactants: R-COOH OH• ..O .. : O-H || : C-O-H . Products: R-COO• H2O ..O .. : O:H || | C-O H
03

Write the deprotonation reaction equation

The deprotonation reaction for the carboxylic acid can be written as follows: R-COOH + OH- → R-COO- + H2O Here, OH- is the hydroxide ion and R-COOH is the given carboxylic acid.
04

Draw the Lewis dot structures for deprotonation

The Lewis dot structures for the reactants and products in the deprotonation reaction are: Reactants: R-COOH OH- ..O .. : O:H || | C-O-H .: Products: R-COO- H2O ..O .. : O:H || | C-O- H
05

Explain why hydroxyl radical is more toxic than hydroxide ion

Hydroxyl radicals (OH•) are more toxic to living systems than hydroxide ions (OH-) because they are highly reactive and can cause oxidative stress in cells, leading to damage or death. The hydroxyl radical is capable of damaging virtually all cellular components, including lipids, proteins, and DNA. This can lead to cellular malfunctioning and eventually cell death if these damages are not repaired. In contrast, hydroxide ions are not as reactive and do not cause such damage, making them less toxic to the living systems.

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