Harvard University Substituent Priority and Activating Deactivating Groups Worksheet

This week’s BTP as 3 (three) questions. As before, all the provided answers have errors. Some are minor, some are major. If an error is made in step 1 but is treated consistently in the following steps, you only need to count it once.

The first step should be for you to write out the correct answer! Then you can identify the errors etc. Please use the provided template. Yes, Question 3 is asking you to solve the problem.

Be The Professor – Week 3
All Given Answers Are Wrong; Identify errors as major or minor
Question 1
Propose a synthetic scheme for the following reaction:
Answer 1 – There are 3 errors
1. HNO3/H2SO4
2. Br2/FeBr3
3.
/FeCl3
4. Sn, HCl
5. NaOH, H2O
6. HCN/CuCN
Question 2
Synthesize the following from benzene:
Answer 2 – There is 1 error in the given answer but it’s a compound error. NOTE: There is more than
one way to complete this synthesis.
1. I2/FeCl3
2. fuming H2SO4
3. HNO3/H2SO4
4. dilute H2SO4
5. Ni, H2
4. NaNO2/H+
5. H2O, heat
Question 3
Use the provided spectral data to determine the structure of the aromatic compound. Propose a synthesis from
benzene in 5 steps or less.
HNMR: 6.72 ppm (1H, d), 6.64 ppm (1H, s), 6.63 ppm (1H, d), 2.02 ppm (3H, s), 1.93 ppm (3H, s), 1.92 (3H,
s)
Answer 3
Proposed Synthesis:
1.
2.
3.
4.
5.
6.
7.
8.
CH3Br/FeBr3
Br2, light
N3
LiAlH4
H2O
CH3I (xs)
Ag2O, H2O
heat
BTP Answer Submission
Question 1
Correct Answer
Put your images and text here. You can add rows/columns as needed. I recommend putting each image in
it’s own cell/row
Errors Identified
I suggest using separate rows for each error. Explain what the error is and if it’s minor or major. Minor may
be forgetting to write a charge. Major would be getting the product of a reaction completely wrong. It’s your
judgement.
Additional Comments
Use this space to clarify anything you’ve submitted above.
Question 2
Correct Answer
Put your images and text here. You can add rows/columns as needed. I recommend putting each image in
it’s own cell/row
Errors Identified
I suggest using separate rows for each error. Explain what the error is and if it’s minor or major. Minor may
be forgetting to write a charge. Major would be getting the product of a reaction completely wrong. It’s your
judgement.
Additional Comments
Use this space to clarify anything you’ve submitted above.