4. For each of the following reactions, draw the arrow-pushing mechanism that leads to the product shown. Use your knowledge of pKa's, nucleophiles, and electrophiles to determine if the reaction shown is likely to happen, and briefly explain your rationale. In the cases where the reaction drawn is not likely, draw the mechanism of the correct reaction. (30 pts) a) + Na + Br NH2 + CH3-1 + |¯ H H Na + Br OH + Br + NH₂ + OH CI + NaBr + + NaBr OH Br + HF + HCI NH

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 57AP: A chemist in need of 2,2-dimethylpentanoic acid decided to synthesize some by reaction of...
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4. For each of the following reactions, draw the arrow-pushing mechanism that leads to the
product shown. Use your knowledge of pKa's, nucleophiles, and electrophiles to determine if
the reaction shown is likely to happen, and briefly explain your rationale. In the cases where the
reaction drawn is not likely, draw the mechanism of the correct reaction. (30 pts)
a)
+
Na +
Br
NH2
+ CH3-1
+ |¯
H H
Na
+
Br
OH
+
Br
+
NH₂
+
OH
CI
+ NaBr
+
+ NaBr
OH
Br
+ HF
+ HCI
NH
Transcribed Image Text:4. For each of the following reactions, draw the arrow-pushing mechanism that leads to the product shown. Use your knowledge of pKa's, nucleophiles, and electrophiles to determine if the reaction shown is likely to happen, and briefly explain your rationale. In the cases where the reaction drawn is not likely, draw the mechanism of the correct reaction. (30 pts) a) + Na + Br NH2 + CH3-1 + |¯ H H Na + Br OH + Br + NH₂ + OH CI + NaBr + + NaBr OH Br + HF + HCI NH
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