Which of the following is the stronger Brønsted base?Select answer from the options below(CH3)3CS-(CH3)2CHS-CH3CH2S-
Question
Which of the following is the stronger Brønsted base?
Select answer from the options below:
(CH3)3CS-
(CH3)2CHS-
CH3CH2S-
Solution
The strength of a Brønsted base is determined by its ability to accept a proton. In this case, we are comparing the basicity of (CH3)3CS-, (CH3)2CHS-, and CH3CH2S-.
The basicity of a molecule is influenced by the stability of its conjugate acid. The more stable the conjugate acid, the stronger the base.
The stability of the conjugate acid is influenced by the ability of the molecule to distribute the positive charge. This is often determined by the inductive effect, where electron-donating groups can stabilize the positive charge.
Looking at the options:
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(CH3)3CS-: The sulfur atom is attached to three methyl groups. Methyl groups are electron-donating, which can help stabilize the positive charge on the sulfur atom in its conjugate acid.
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(CH3)2CHS-: The sulfur atom is attached to two methyl groups and one hydrogen. The inductive effect is less than in the first case.
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CH3CH2S-: The sulfur atom is attached to an ethyl group. The inductive effect is the least in this case.
Therefore, (CH3)3CS- is the strongest Brønsted base among the given options.
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