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Acid Strength

Posted: Fri Dec 04, 2015 8:27 pm
by Nisha Patel 3I
In this problem, how do you know that H has more electron withdrawing ability than CH3?

Fall 2013 Final Exam: #Q7B

"List the following acids in order of increasing strength and explain why: CF3COOH (1), CH3COOH (2), CCl3COOH (3), C(CH3)3COOH (4)"

Answer: 4<2<3<1
Electron withdrawing ability F>Cl>H>CH3

Re: Acid Strength

Posted: Fri Dec 04, 2015 8:32 pm
by Sandeep Gurram 2E
Dr. Lavelle had an excellent explanation of this exact problem in his review session for the final. Basically, CH3 is a more electron rich species than H is, and therefore has more of a negative charge associated with it. In fact H is basically considered a positive species. Because of this, CH3 does not pull on electron dense regions as hard as H can. Hope that helped.