NAME__________________________________________________
CM-UY 2213
Organic Chemistry I
Problem Set 7
Due November 11, 2025, by 11:59 pm on Gradescope
INSTRUCTIONS:
1. Download or print the problem set and work out your answers in the space provided. If
you try to submit with a file separate from the problem set template, Gradescope will not
accept your submission!
2. Scan or save your completed problem set as a PDF.
3. Upload your file to Gradescope by the deadline.
4. Problem sets will be graded 50% for completion and 50% for correctness. One of the
pages will be randomly selected to be graded for correctness, while all other pages will be
checked for completion. It is thus in your best interest to complete each problem to the
best of your ability.
5. Once grades have been released, compare your answers with the key uploaded to
Brightspace, especially for the problems that were not graded for correctness. If you do
not take the time to correct your answers, you will not learn from your mistakes and this
will likely reflect on the exam!
, Part 1. Reaction mechanisms
i. Draw the arrow pushing mechanism of the E1 reaction between 2-chloro-2-methylbutane and
ethanol and heat.
Sketch a reaction coordinate diagram on the axes below and add in all reactants, products, and
intermediates. What does the diagram tell us about the rate determining step of the E1 reaction?
Energy
Reaction Coordinate
Go back to Problem Set 6 and compare the reaction coordinate diagram you just drew with the
one you drew for the SN1 reaction. How does the E1 reaction coordinate diagram look different
from the SN1 diagram?
CM-UY 2213
Organic Chemistry I
Problem Set 7
Due November 11, 2025, by 11:59 pm on Gradescope
INSTRUCTIONS:
1. Download or print the problem set and work out your answers in the space provided. If
you try to submit with a file separate from the problem set template, Gradescope will not
accept your submission!
2. Scan or save your completed problem set as a PDF.
3. Upload your file to Gradescope by the deadline.
4. Problem sets will be graded 50% for completion and 50% for correctness. One of the
pages will be randomly selected to be graded for correctness, while all other pages will be
checked for completion. It is thus in your best interest to complete each problem to the
best of your ability.
5. Once grades have been released, compare your answers with the key uploaded to
Brightspace, especially for the problems that were not graded for correctness. If you do
not take the time to correct your answers, you will not learn from your mistakes and this
will likely reflect on the exam!
, Part 1. Reaction mechanisms
i. Draw the arrow pushing mechanism of the E1 reaction between 2-chloro-2-methylbutane and
ethanol and heat.
Sketch a reaction coordinate diagram on the axes below and add in all reactants, products, and
intermediates. What does the diagram tell us about the rate determining step of the E1 reaction?
Energy
Reaction Coordinate
Go back to Problem Set 6 and compare the reaction coordinate diagram you just drew with the
one you drew for the SN1 reaction. How does the E1 reaction coordinate diagram look different
from the SN1 diagram?
