17.5: Nitriles

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Jan 4, 2023
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- 17.4: Super Leaving Groups
- 17.6: Named Reactions

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There is one more functional group that fits into the reactivity series. Notice that each of the electrophiles in the series (with the exception of aldehydes/ketones) has three bonds to heteroatoms. The other functional group that fits into this category is the nitrile, with three bonds to nitrogen. Its reactivity comes in between the amide and ester:

Screen Shot 2023-01-04 at 9.24.56 AM.png

Let’s look at its reactivity under acidic and basic hydrolytic conditions:

1. Acidic hydrolysis:

Screen Shot 2023-01-04 at 9.36.59 AM.png

2. Basic hydrolysis

Screen Shot 2023-01-04 at 9.37.05 AM.png

Under basic conditions, the amidate intermediate is now even less electrophilic than amides due to the negative charge. It will still react to give carboxylates (or carboxylic acids upon protonation), but more forcing conditions are needed.

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