Question
would the single hydrogen attatched to a carbonyl (like aldehyde) just have a pKa around 50 like an alkane group?

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Answer #1

No

The encircled hydrogen attached to the carbonyl carbon in an aldehyde or ketone is far more acidic than a hydrogen of an alkane.

This is because of the greater stability of the conjugate base for the first. If there is deprotonation, the negative charge over the carbon in the conjugate base resides on an sp2 hybrid carbon for the carbonyl compound and an sp3 hybrid carbon for an alkane.

An sp2 carbon has more s character than an sp3 hybridized carbon. A greater s character directly relates to lower energy and more stability.

The more stable is the conjugate base, more acidic is the original compound.

Greater acidity means lower pkavalue. So, the single hydrogen attached to a carbonyl group has much less pka(for example methane has a value around 13) than that of an alkane which has a value around 50.

Sphyboiliue O (H) O ㅐ } I (mone audie) 너 { cha 랭 왕대 2 sp hybridized (les ocides

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