CBSE (Science) Class 12CBSE
Share
Notifications

View all notifications

Arrange the following compounds in increasing order of their property as indicated: CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) - CBSE (Science) Class 12 - Chemistry

Login
Create free account


      Forgot password?

Question

Arrange the following compounds in increasing order of their property as indicated:

CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)

Solution

After losing a proton, carboxylic acids gain a negative charge as shown:

`R - COOH ->  R- COO^(-) + H^(+)`

Now, any group that will help stabilise the negative charge will increase the stability of the carboxyl ion and as a result, will increase the strength of the acid. Thus, groups having +I effect will decrease the strength of the acids and groups having −I effect will increase the strength of the acids. In the given compounds, −CH3 group has +I effect and Br group has −I effect. Thus, acids containing Br are stronger.

Now, the +I effect of isopropyl group is more than that of n-propyl group. Hence, (CH3)2CHCOOH is a weaker acid than CH3CH2CH2COOH.

Also, the −I effect grows weaker as distance increases. Hence, CH3CH(Br)CH2COOH is a weaker acid than CH3CH2CH(Br)COOH.

Hence, the strengths of the given acids increase as:

(CH3)2CHCOOH < CH3CH2CH2COOH < CH3CH(Br)CH2COOH < CH3CH2CH(Br)COOH

  Is there an error in this question or solution?

APPEARS IN

 NCERT Solution for Chemistry Textbook for Class 12 (2018 to Current)
Chapter 12: Aldehydes, Ketones and Carboxylic Acids
Q: 12.2 | Page no. 378

Video TutorialsVIEW ALL [1]

Solution Arrange the following compounds in increasing order of their property as indicated: CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH (acid strength) Concept: Aldehydes and Ketones - Structure of the Carbonyl Group.
S
View in app×