Be sure to answer all parts. Consider both 5-methyl-1,3-cyclopentadiene (A) and 7-methyl-1,3,5-cycloheptatriene (B). Which labeled H atom is most acidic? Hb is most acidic because its conjugate base is aromatic. Hc is most acidic because its conjugate base is antiaromatic. Ha is most acidic because its conjugate base is antiaromatic. Hd is most acidic because its conjugate base is aromatic. Which labeled H atom is least acidic? Ha is least acidic because its conjugate base is aromatic. Hb is least acidic because its conjugate base is antiaromatic. Hd is least acidic because its conjugate base is aromatic. Hc is least acidic because its conjugate base is antiaromatic.

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The hydrogen that is attached at the tertiary position on the heptatriene (at the 7-methyl) would be very acidic, as removal would leave a positive charge that could be moved throughout the ring through resonance. This would mean that the three double bonds would be participating in resonance, and the deprotonated structure would be aromatic, thus making this favorable.

The hydrogen that is attached at the tertiary position on the pentadiene (5-methyl) would NOT be acidic, as removal would cause an antiaromatic structure.

Any other hydrogens would NOT be acidic. Those vinylic to their respective double bonds would seriously destabilize the double bond if removed, and hydrogens attached to the methyl group jutting off the ring have no incentive to leave the carbon.

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Due to the conjugate base of the hydrogen atom is aromatic, Hb is regarded as the most acidic. Because the conjugate base of the hydrogen atom Hc is anti-aromatic, it is the least acidic.

The correct options are:

(A) - (a)

(B) - (d)

What are the most and the least acidic hydrogen atom?

The hydrogen connected at the heptatriene's tertiary position (at the 7-methyl) would be particularly acidic, as its removal would leave a positive charge that could be transported around the ring via resonance.

The hydrogen connected to the pentadiene (5-methyl) at the tertiary position would not be acidic, as removing it would result in an anti-aromatic structure.

Thus, the least acidic H atom is Hc and the most acidic H atom is Hb.

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