Page 2 of 16
1) Identify whether the following molecules are aromatic, antiaromatic or non-aromatic (4 Points)
a) ___________________
b) ___________________
c) ___________________
d) ___________________
2) For the following compound:
a) What is the hybridization of the indicated atoms? (3 points)
C=
O=
N=
b) What type of molecular orbitals connect the following atoms to other atoms? (5 points)
C=
O=
N=
, Page 3 of 16
3) Write a detailed mechanism for this transformation (8 points)
4) On the structure below, either of the two nitrogen atoms can react with NaH.
a) Draw the two possible conjugate bases that can be formed from this reaction. (2 points).
b) Underline the weakest base in part a. (1 Point)
c) Justify your answer in part b (5 Points).
d) Using your answer from part b, predict the site of de-protonation on the original molecule
and briefly explain your choice. (2 Points)
1) Identify whether the following molecules are aromatic, antiaromatic or non-aromatic (4 Points)
a) ___________________
b) ___________________
c) ___________________
d) ___________________
2) For the following compound:
a) What is the hybridization of the indicated atoms? (3 points)
C=
O=
N=
b) What type of molecular orbitals connect the following atoms to other atoms? (5 points)
C=
O=
N=
, Page 3 of 16
3) Write a detailed mechanism for this transformation (8 points)
4) On the structure below, either of the two nitrogen atoms can react with NaH.
a) Draw the two possible conjugate bases that can be formed from this reaction. (2 points).
b) Underline the weakest base in part a. (1 Point)
c) Justify your answer in part b (5 Points).
d) Using your answer from part b, predict the site of de-protonation on the original molecule
and briefly explain your choice. (2 Points)
