NAME__________________________________________________
CM-UY 2213
Organic Chemistry I
Problem Set 8
Due December 2, 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. Addition of HX and H3O+ to alkenes
i. When we first learned the addition of HX and H3O+ to alkenes, we had not yet learned
stereochemistry. Now that we have, we can apply stereochemistry to these reactions. As a
carbocation is formed, a racemic mixture of enantiomers will result if the addition of the
nucleophile makes a chirality center, similar to an SN1 reaction. Circle all of the following
alkenes that would make a racemic mixture of enantiomers upon addition of HBr.
ii. Substituents on the alkene also affect what product is formed. For the following reactions,
draw the arrow-pushing mechanism to show how (and why) the product(s) shown are formed.
HCl
Cl
Cl
Cl
H3O+
HO
HO
OH
HBr
Br
Br
CM-UY 2213
Organic Chemistry I
Problem Set 8
Due December 2, 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. Addition of HX and H3O+ to alkenes
i. When we first learned the addition of HX and H3O+ to alkenes, we had not yet learned
stereochemistry. Now that we have, we can apply stereochemistry to these reactions. As a
carbocation is formed, a racemic mixture of enantiomers will result if the addition of the
nucleophile makes a chirality center, similar to an SN1 reaction. Circle all of the following
alkenes that would make a racemic mixture of enantiomers upon addition of HBr.
ii. Substituents on the alkene also affect what product is formed. For the following reactions,
draw the arrow-pushing mechanism to show how (and why) the product(s) shown are formed.
HCl
Cl
Cl
Cl
H3O+
HO
HO
OH
HBr
Br
Br
