The C-H bond in acetone, (CH),C=0, has a pK, of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH,CH,CH3 (pK, = 50). Use skeletal structures for the resonance structures. Resonance structures: draw structure ... draw structure ... (negative charge on C) (negative charge on O) Acetone is much more acidic than propane because: Acetone's conjugate base has fewer resonance structures than propane's conjugate base. The negative charge on acetone's conjugate base is stabilized by resonance. The negative charge on acetone's conjugate base is stabilized by inductance.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
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Chapter20: Acidity And Pka Of Phenols
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The C-H bond in acetone, (CH,),C=0, has a pk, of 19.2. Draw two resonance structures for its
conjugate base. Then, explain why acetone is much more acidic than propane, CH,CH,CH, (pK,= 50).
Use skeletal structures for the resonance structures.
Resonance structures:
draw structure
draw structure
(negative charge on C)
(negative charge on O)
Acetone is much more acidic than propane because:
Acetone's conjugate base has fewer resonance structures than propane's conjugate base.
The negative charge on acetone's conjugate base is stabilized by resonance.
The negative charge on acetone's conjugate base is stabilized by inductance,
Acetone's higher molecular mass makes it more acidic than propane.
Transcribed Image Text:The C-H bond in acetone, (CH,),C=0, has a pk, of 19.2. Draw two resonance structures for its conjugate base. Then, explain why acetone is much more acidic than propane, CH,CH,CH, (pK,= 50). Use skeletal structures for the resonance structures. Resonance structures: draw structure draw structure (negative charge on C) (negative charge on O) Acetone is much more acidic than propane because: Acetone's conjugate base has fewer resonance structures than propane's conjugate base. The negative charge on acetone's conjugate base is stabilized by resonance. The negative charge on acetone's conjugate base is stabilized by inductance, Acetone's higher molecular mass makes it more acidic than propane.
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