CHEM 3341B Acid strength questions

CHEM 3341B Acid strength questions - Since the conjugate...

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CHEM 3341B Lecture Questions 1. Which is a stronger acid, CH 3 CH 2 OH or CH 3 CH 2 SH? The second acid, CH 3 CH 2 SH, is stronger. This is because the sulfur atom is larger than oxygen. The larger size of sulfur makes it better able to accommodate a negative charge (larger volume of space for electrons). Since the conjugate base CH 3 CH 2 S is weaker or more stable, CH 3 CH 2 SH is the stronger acid. 2. Explain why amino acids are stronger acids than “normal” carboxylic acids. The amino acid is a stronger acid because inductive electron withdrawal due to the amino group (containing the nitrogen) stabilizes the conjugate base. The weaker conjugate base leads to a stronger acid. CHEM 3341B Lecture Questions 1. Which is a stronger acid, CH 3 CH 2 OH or CH 3 CH 2 SH? The second acid, CH 3 CH 2 SH, is stronger. This is because the sulfur atom is larger than oxygen. The larger size of sulfur makes it better able to accommodate a negative charge (larger volume of space for electrons).
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Unformatted text preview: Since the conjugate base CH 3 CH 2 S is weaker or more stable, CH 3 CH 2 SH is the stronger acid. 2. Explain why amino acids are stronger acids than normal carboxylic acids. The amino acid is a stronger acid because inductive electron withdrawal due to the amino group (containing the nitrogen) stabilizes the conjugate base. The weaker conjugate base leads to a stronger acid. C O OH C H 2 N H H amino acid, pKa ~2.3 C O OH C H H H carboxylic acid, pKa 4.76 C O O C H 2 N H H C O O C H H H Inductive electron withdrawal by the nitrogen atom makes the conjugate base of the amino acid more stable. C O OH C H 2 N H H amino acid, pKa ~2.3 C O OH C H H H carboxylic acid, pKa 4.76 C O O C H 2 N H H C O O C H H H Inductive electron withdrawal by the nitrogen atom makes the conjugate base of the amino acid more stable....
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