3 When undertaking an acid/base reaction in the lab, it is always critical to kn

Question

3 When undertaking an acid/base reaction in the lab, it is always critical to know which base to use to deprotonate a particular compound. Consider the four bases shown: sodium acetate (A), sodium methoxide (B), sodium amide (C) and methyllithium (D). For each compound shown, write the letter of the base that is strong enough to quantitatively deprotonate the most acidic hydrogen in the molecule, but is the weakest base that can do this quantitatively. Some compounds can be quantitatively deprotonated by more than one base, but only write the letter corresponding to the weakest base that can cause the deprotonation. If no bases can quantitatively deprotonate the compound, then write NONE in the box. (3 points each) CH3ONa NH2Na OH OH SH

Explanation / Answer

I will tell you the letters, you only need to apply basics knowledge of acid - base reaction, and the bulkiness of the base and nucleophile. You need to look very well in the molecule if they have an acidic hydrogen. If they do have it, then use the base to do that basing on the structure of the same. Usually, a less bulky base is a very strong base rather than a bulky one.

I will tell you the letters in order by columns:

1. B

2. A

3. B

4. C

Now the second column:

5. B

6. None (it does not have an acidic hydrogen)

7. None.

8. A or B.

Hope this helps

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