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Decreasing order of acid strength is : ...

Decreasing order of acid strength is : `Phunderset((A))-OH," " Ph-underset((B))CH_(2)-OH," "Ph-CO_(2)H," " Ph-underset((D))CH_(2)-overset(o+)NH_(3)`

A

`BgtAgtCgtD`

B

`CgtAgtBgtD`

C

`CgtAgtDgtB`

D

`CgtBgtAgtD`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the decreasing order of acid strength for the compounds given, we need to analyze the stability of the conjugate bases formed when each compound donates a proton (H+). The more stable the conjugate base, the stronger the acid. ### Step-by-Step Solution: 1. **Identify the Compounds:** - (A) Ph-OH (Phenol) - (B) Ph-CH2-OH (Benzyl alcohol) - (C) Ph-CO2H (Benzoic acid) - (D) Ph-CH2-NH3+ (Benzylammonium ion) 2. **Determine the Conjugate Bases:** - For (A) Ph-OH, the conjugate base is Ph-O⁻ (phenoxide ion). - For (B) Ph-CH2-OH, the conjugate base is Ph-CH2-O⁻ (benzyl oxide ion). - For (C) Ph-CO2H, the conjugate base is Ph-CO2⁻ (benzoate ion). - For (D) Ph-CH2-NH3+, the conjugate base is Ph-CH2-NH2 (benzylamine). 3. **Analyze the Stability of Conjugate Bases:** - **(A) Ph-O⁻:** The negative charge on oxygen can be delocalized due to resonance with the aromatic ring, making it relatively stable. - **(B) Ph-CH2-O⁻:** The negative charge is localized on the oxygen and does not have resonance stabilization from the aromatic ring, making it less stable than Ph-O⁻. - **(C) Ph-CO2⁻:** The negative charge is delocalized over two oxygen atoms in the carboxylate ion, making it very stable and thus, benzoic acid is a strong acid. - **(D) Ph-CH2-NH2:** This is a neutral amine and does not have a negative charge, making it the least acidic. 4. **Rank the Acids:** - **Strongest Acid:** (C) Ph-CO2H (Benzoic acid) - due to the resonance stabilization of the conjugate base. - **Next Strongest:** (A) Ph-OH (Phenol) - resonance stabilization of phenoxide ion. - **Next:** (B) Ph-CH2-OH (Benzyl alcohol) - no resonance stabilization. - **Weakest Acid:** (D) Ph-CH2-NH3+ (Benzylammonium ion) - neutral and not acidic. 5. **Final Order:** - The decreasing order of acid strength is: **Ph-CO2H > Ph-OH > Ph-CH2-OH > Ph-CH2-NH3+**. ### Final Answer: The order of decreasing acid strength is: **C > A > B > D**.

To determine the decreasing order of acid strength for the compounds given, we need to analyze the stability of the conjugate bases formed when each compound donates a proton (H+). The more stable the conjugate base, the stronger the acid. ### Step-by-Step Solution: 1. **Identify the Compounds:** - (A) Ph-OH (Phenol) - (B) Ph-CH2-OH (Benzyl alcohol) - (C) Ph-CO2H (Benzoic acid) ...
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