Identify the Bonds Made and The Bonds Broken in The Reaction Questions

NAME:___________________________

This is a chance to look again at topics covered on exams 3 & 4. This is not a mandatory assignment.

  • If the supplement is not completed, the exams 3 & 4 grades will be the percentage earned on the first submission (the number currently in the D2L gradebook for each).
  • After feedback, the points will be added to whichever exam will increase the overall class grade the most (Dr. Maki will do this calculation, you do not have to choose).
  • A maximum of 7.5% (4.5 points out of 60) will be added to the exam scores. No exam scores will go above 100%.

QUESTION 1 (added 1.5% = 0.9 points/60): Identify the bonds made and the bonds broken in the following reaction. Classify the reaction as one of the three types of reactions we have discussed.

ClCl

C

F

NR

2

F-NR

2

QUESTION 2 (added 2% = 1.2 points/60): In the reaction above, The F-NR2 reagent is remarkable in that the fluorine reacts as F+. Propose a mechanism for this transformation that draws all intermediates and shows all arrows.

ClCl

C

F

NR

2

F-NR

2

EXAMS 3&4 SUPPLEMENT – NAME:___________________________

QUESTION 3 (added 2% = 1.2 points/60): Cyanoform (HC4N3, see structure below) was recently isolated for the first time. Due to its instability, it took more than one hundred years to go from the first attempted synthesis to a successful isolation of this compound. Draw the conjugate base and provide reasoning for why cyanoform is so reactive.

N H N

C

C

C

N

+ base

unstable

QUESTION 4 (added 2% = 1.2 points/60): Show the mechanism responsible for the following transformation.

Br Ts-NH2 O N Ts

Br

O

Br

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