3a) Amides are moderately acidic at the N atom, so they can be alkylated in a fashion that is quite similar to the alkylation of ketones and aldehydes. Predict the product of the reaction shown here, and draw its complete, detailed mechanism. N 1. NaH 2. CI ? 3b) If in Step 2 above, the allylic chloride is replaced by another electrophile - Me-SiCl - a different product forms. Predict what this product is & draw the mechanism. Hint: the formation of Si-O bonds is very thermodynamically favorable.

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3a)
Amides are moderately acidic at the N atom, so they
can be alkylated in a fashion that is quite similar to the
alkylation of ketones and aldehydes. Predict the product
of the reaction shown here, and draw its complete,
detailed mechanism.
1. NaH
2.
?
3b)
If in Step 2 above, the allylic chloride is replaced by another electrophile - Me-SiCl
- a different product forms. Predict what this product is & draw the mechanism.
Hint: the formation of Si-O bonds is very thermodynamically favorable.
Transcribed Image Text:3a) Amides are moderately acidic at the N atom, so they can be alkylated in a fashion that is quite similar to the alkylation of ketones and aldehydes. Predict the product of the reaction shown here, and draw its complete, detailed mechanism. 1. NaH 2. ? 3b) If in Step 2 above, the allylic chloride is replaced by another electrophile - Me-SiCl - a different product forms. Predict what this product is & draw the mechanism. Hint: the formation of Si-O bonds is very thermodynamically favorable.
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