Home
Class 12
CHEMISTRY
Consider the methyl substituted benzoic ...

Consider the methyl substituted benzoic acids.
1. `PhCOOH`
2. `o-CH_(3)C_(6)H_(4)COOH`
3. `p - CH_(3)C_(6)H_(4)COOH`
4. `m-CH_(3)C_(6)H_(4)COOH`
The correct sequence of acidity is

A

`1 lt 2 lt 3 lt 4`

B

`2 lt 3 lt 4 lt1`

C

`3 lt 4 lt 1 lt 2`

D

`3 lt 4 lt 2 lt 1`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the correct sequence of acidity for the methyl substituted benzoic acids, we will analyze the effects of the methyl (−CH₃) substituent on the acidity of benzoic acid. The compounds we are considering are: 1. Benzoic acid (PhCOOH) 2. Ortho-methylbenzoic acid (o-CH₃C₆H₄COOH) 3. Para-methylbenzoic acid (p-CH₃C₆H₄COOH) 4. Meta-methylbenzoic acid (m-CH₃C₆H₄COOH) ### Step 1: Understand the acidity of benzoic acid Benzoic acid (PhCOOH) has a carboxylic acid group (−COOH) that can donate a proton (H⁺). The strength of an acid is determined by its ability to donate protons and the stability of its conjugate base (the anion formed after losing a proton). ### Step 2: Analyze the substituent effects - **Ortho (o-CH₃)**: The methyl group is positioned ortho to the carboxylic acid group. The ortho effect can lead to steric hindrance and destabilization of the conjugate base (−COO⁻) due to the proximity of the methyl group. However, it can also enhance the acidity due to resonance effects being disrupted, leading to a more stable conjugate base. - **Para (p-CH₃)**: The methyl group is positioned para to the carboxylic acid group. In this case, the methyl group can donate electron density through hyperconjugation, which destabilizes the conjugate base (−COO⁻) and decreases the acidity of the acid. - **Meta (m-CH₃)**: The methyl group is positioned meta to the carboxylic acid group. Here, the methyl group does not significantly affect the resonance stabilization of the conjugate base, leading to a moderate acidic strength. ### Step 3: Compare the acidity 1. **Ortho-methylbenzoic acid (o-CH₃C₆H₄COOH)**: The steric hindrance and disruption of resonance make this acid the strongest. 2. **Benzoic acid (PhCOOH)**: The baseline acidity without any substituents. 3. **Meta-methylbenzoic acid (m-CH₃C₆H₄COOH)**: The methyl group has a weaker effect on acidity compared to the ortho and para positions. 4. **Para-methylbenzoic acid (p-CH₃C₆H₄COOH)**: The electron-donating effect of the methyl group decreases the acidity the most. ### Conclusion The correct sequence of acidity from strongest to weakest is: **o-CH₃C₆H₄COOH > PhCOOH > m-CH₃C₆H₄COOH > p-CH₃C₆H₄COOH** Thus, the final order is: **2 > 1 > 4 > 3**
Promotional Banner

Similar Questions

Explore conceptually related problems

Consider the acidity of the carboxylic acids : (i) PHCOOH" "(ii) o-NO_(2)C_(6)H_(4)COOH" "(iii) p-NO_(2)C_(6)H_(4)COOH" "(iv) m-NO_(2)C_(6)H_(4)COOH

Consider the acidity of the carboxylic acids: (1) PhCOOH (2) o-NO_(2) C_(6) H_(4) COOH (3) p-NO_(2) C_(6) H_(4) COOH (4) m-NO_(2) C_(6) H_(4) COOH Which of the following order is correct?

Consider the acidity of the carboxylic acids: (a) PhCOOH (b) o-NO_(2) C_(6) H_(4) COOH (c) m-NO_(2) C_(6) H_(4) COOH (d) p-NO_(2) C_(6) H_(4) COOH Which of the following is the strongest acid and why?

(i) F_(3)C-COOH, (ii) CH_(3)COOH , (iii) C_(6)H_(5)COOH, (iv) CH_(3)CH_(2)COOH Correct order of pK_(a) value is :

NH_(4)OH , NaOH, CH_(3)COOH , H_(2)S

Arrange the following anilines in decreasing order of basicity 1. C_(6)H_(5)NH_(2) 2. o-CH_(3)C_(6)H_(4)NH_(2) 3. m-CH_(3)C_(6)H_(4)NH_(2) 4. p-CH_(3)C_(6)H_(4)NH_(2)

(1) C_(6)H_(5)-overset(O)overset(||)C-C_(6)H_(5) (2) C_(6)H_(5)-CHO (3) p-CH_(3)-C_(6)H_(4)-CHO (4) p-CH_(3)O-C_(6)H_(4)-CHO Correct order for nucleophilic addition reaction :

Give the IUPAC name of m-ClCH_(2)C_(6)H_(4)CH_(2)C(CH_(3))_(3)

Arrange the following compounds in the increasing order of their property as indicated: i. Acetaldehyde, acetone, di-tert-butyl ketone, methyl tert-butyl ketone (reactivity towards HCN). ii. CH_(3)CH_(2)CH(Br)COOH, CH_(3)CH(Br)CH_(2)COOH, (CH_(3))_(2)CHCOOH, CH_(3)CH_(2)CH_(2)COOH (acidic strength). iii. Benzoic acid, 4-nitrobenzoic acid, 3,4-dinitro-benzoic acid, 4-methoxybenzoic acid (acidic strength).

(a) Arrange the following in an increasing order of their indicated property. (i) Benzoic acid ,4- Nitrobenzoc acid ,3,4 - Dinitrobenzoic acid, 4- Methoxybenzoic acid (acid strength) (ii) CH_(3)CH_(2)CH(Br)COOH,CH_(3)CH(Br)CH_(2)COOH , (CH_(3))_(2)CHCOOH,CH_(3)CH_(2)CH_(2)COOH (acid strength) (b) How would you bring about the following conversions : (i) Propanone to propene (ii) Benzoic acid to Benzaldehyde (iii) Bromobenzene to 1- phenylethanol