NAME__________________________________________________
CM-UY 2213
Organic Chemistry I
Problem Set 9
Due December 9, 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. Radicals
i. Differentiate a homolytic cleavage of a C-H bond from a heterolytic cleavage. What
differences are there in the products?
Homolytic cleavage results in neutral products, while heterolytic cleavage results in charged
products.
ii. Explain why the homolytic cleavage of the C-CH3 bond in butane takes more energy than the
homolytic cleavage of the C-CH3 bond in 1-butene. What is the relative energy of the products?
iii. Give an example of each of the following types of radical reactions different from those given
in class: abstraction, disproportionation, b-cleavage, and dimerization. Identify each of these as
an initiation, propagation, or termination.
CM-UY 2213
Organic Chemistry I
Problem Set 9
Due December 9, 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. Radicals
i. Differentiate a homolytic cleavage of a C-H bond from a heterolytic cleavage. What
differences are there in the products?
Homolytic cleavage results in neutral products, while heterolytic cleavage results in charged
products.
ii. Explain why the homolytic cleavage of the C-CH3 bond in butane takes more energy than the
homolytic cleavage of the C-CH3 bond in 1-butene. What is the relative energy of the products?
iii. Give an example of each of the following types of radical reactions different from those given
in class: abstraction, disproportionation, b-cleavage, and dimerization. Identify each of these as
an initiation, propagation, or termination.
