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CH(3)"CCl"(3)overset("hydrolysis")rarr "...

`CH_(3)"CCl"_(3)overset("hydrolysis")rarr " acid - 2"`
Correct answer is

A

`(pK_(a))_(HCN) gt (pK_(a))_("acid - 2")`

B

`(pK_(a))_("HCN")=(pK_(a))_("acid - 2")`

C

`(pK_(a))_("HCN")lt (pK_(a))_("acid-2")`

D

All of these

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem, we need to analyze the hydrolysis of CH₃CCl₃ and determine the relationship between the pKa values of HCN and the resulting acid (which is acetic acid, CH₃COOH). ### Step-by-Step Solution: 1. **Identify the Reactant:** The reactant is CH₃CCl₃ (trichloroethane). 2. **Understand the Hydrolysis Reaction:** Hydrolysis involves the reaction of CH₃CCl₃ with water, resulting in the substitution of chlorine atoms with hydroxyl groups (OH). The reaction can be represented as: \[ CH₃CCl₃ + H₂O \rightarrow CH₃C(OH)₃ \] 3. **Mechanism of Hydrolysis:** The hydrolysis of CH₃CCl₃ follows an SN2 mechanism, where the nucleophile (water) attacks the carbon atom bonded to the chlorine atoms, leading to the formation of a tertiary alcohol (CH₃C(OH)₃). 4. **Formation of Acetic Acid:** The tertiary alcohol (CH₃C(OH)₃) can lose a water molecule to form acetic acid (CH₃COOH): \[ CH₃C(OH)₃ \rightarrow CH₃COOH + H₂O \] 5. **Determine the pKa Values:** - The pKa of acetic acid (CH₃COOH) is approximately 4.76. - The pKa of hydrogen cyanide (HCN) is approximately 9.2. 6. **Compare the Strength of the Acids:** - Acetic acid is a stronger acid than HCN because it has a lower pKa value. - The strength of an acid is inversely related to its pKa value; a lower pKa indicates a stronger acid. 7. **Conclusion:** Since acetic acid is a stronger acid than HCN, we can conclude that: \[ \text{pKa of acetic acid} < \text{pKa of HCN} \] ### Final Answer: The correct relationship is: \[ \text{pKa of acetic acid} < \text{pKa of HCN} \]
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