Alcohols + Phenol Reactions Flashcards

1
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4
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5
Q

Identify the one that is more acidic:

A

The first compound is more acidic because the
conjugate base of a primary alcohol will be more easily solvated than the conjugate base of a tertiary alcohol.
The better solvated, more stable conjugate base is the weaker conjugate base, and is related to the stronger parent acid:

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6
Q

Identify the one that is more acidic:

A

The first compound is more acidic because the
electron-withdrawing effects of the chlorine atoms
stabilize the conjugate base. The more stable conjugate base is the weaker conjugate base, and is related to the stronger parent acid:

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7
Q

Identify the one that is more acidic:

A

The second compound is more acidic because its
conjugate base is more stabilized by resonance, with the negative charge spread over two oxygen atoms, rather than just one oxygen atom. The more stable conjugate base is the weaker conjugate base, and is related to the stronger parent acid:

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8
Q

Identify the one that is more acidic:

A

The second compound (phenol) is more acidic
because its conjugate base is stabilized by resonance. In contrast, the conjugate base of the first compound (t-BuOH) is not resonance-stabilized. The more stable conjugate base is the weaker conjugate base, and is related to the stronger parent acid:

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9
Q

Identify the reagents that you would use to accomplish the following transformation:

A
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10
Q

Identify the reagents that you would use to accomplish the following transformation:

A
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11
Q

Identify the reagents that you would use to accomplish the following transformation:

A
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12
Q

Identify the reagents that you would use to accomplish the following transformation:

A
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13
Q

Identify the reagents that you would use to accomplish the following transformation:

A
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14
Q

Identify the reagents that you would use to accomplish the following transformation:

A
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15
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