Alkene Reaction Practice Problem Set

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Alkene reactions are the foundation for all future organic chemistry reactions and mechanisms. To help you build that solid foundation I’ve put together this short quiz testing your knowledge of reactions, reagents, products and additional molecule concepts.

These questions range from medium to tricky and should be completed AFTER you’ve studied my Alkene reaction video series since each video already contains a few simple practice problems.

Take your time and think through each question. If you’re not sure how to proceed click the ‘hint’ link for the related mechanism tutorial video. Once finished scroll down and grab a free copy of the solutions.

Alkene Practice Question 1

Identify the reagent and solvent required to carry out this reaction

hydrohalogenation alkene reaction practice question

Hint – if you’re stuck on this reaction watch this video to learn the mechanism

Alkene Practice Question 2

Identify the product formed when this alkene reactions with Cl2 in water. Pay particular attention to stereochemistry.

chlorohydrin alkene reaction practice question

Hint: There may be more than 1 product. For help with this reaction click to watch the mechanism video

Alkene Practice Question 3

Identify the product formed when the following alkene is reacted with BH3 and THF, then followed up with H2O2 and NaOH

hydroboration oxidation alkene reaction practice question

Hint: This is an anti-markovnikov reaction.

 

Alkene Practice Question 4

Identify the starting alkene that will yield the product shown when reacted with chlorine in CCl4. Pay particular attention to the stereochemistry of product.

halogenation alkene reaction practice question

Hint: Stuck on the stereochemistry of this question? Watch the reaction video here to review this reaction

Alkene Practice Question 5

Identify the reagent and solvent required to transform the starting cycloalkene to the given ether.

acid catalyzed alcohol addition alkene reaction practice question

Hint: Water and alcohol undergo similar reactions. Click for the mechanism video

 

Alkene Practice Question 6

Identify the product when the following alkene reacts with Hg(oAc)2 in alcohol followed by NaBH4

alkoxymercuration demercuration reduction alkene reaction practice question

Hint: Pay close attention to each of the given reagents. Stuck on this reaction? Click for the reaction video

Alkene Practice Question 7

Identify the product formed with the given bicycloalkene reacts with Bromine in CH2Cl2. Be sure to include all possible products.

alkene bromination alkene reaction practice question

Hint: Don’t let the complexity of the molecule throw you off. If you know this reaction you’ll get the product

 

Alkene Practice Question 8

Identify the product formed when this alkene reactions with sulfuric acid in an ethanol solution

acid catalyzed alcohol addition with methyl shift alkene reaction practice question

Hint: Pay special attention to the reagents, solvents, and stability of the intermediates. Stuck? review this video

 

Alkene Practice Question 9

Identify the product formed when the given alkene reacts with hydronium

acid catalyzed hydration with hydride shift alkene reaction practice question

Hint: Pay special attention to the stability of the reaction intermediate. Need help? watch this video

Alkene Practice Question 10

Identify the reagents required to bring about this alkene to alcohol transformation.

oxymercuration demercuration reduction alkene reaction practice question

Hint: Consider how the intermediate impacts the regioselectivity of this reaction. Stuck? Watch this video.

Alkene Practice Question 11

Identify the product formed when the alkene below reacts with bromine in a methanol solution.

bromohydrin with alcohol alkene reaction practice question

 

Hint: Consider how the solvent impacts the intermediate. Need help? Watch this video

 

Alkene Practice Question 12

Identify the product when the alkene below reacts with sulfuric acid in water.

acid catalyzed hydration alkene reaction practice question

Hint: Don’t overthink it. Sometimes tricky looking reactants yield simple products. Tutorial video here.

 

Alkene Practice Question 13

Identify the product when the following alkene reacts with HCl in CCl4.

hydrochlorination alkene reaction practice question

Hint: This is a fun (read TRICK) question. Pay careful attention to the logic BEHIND Markovnikov’s rule! Click HERE to study the reaction mechanism.

 

Alkene Practice Question 14

Identify the product when the alkene below reacts with HBr.

hydrobromination with ring expansion and methyl shift

Hint: Other than degree of substitution, what ELSE can cause a carbocation rearrangement? Need help? Watch this video.

Alkene Practice Question 15

Identify the product when the alkene below is reacted with sulfuric acid.

intramolecular acid catalyzed alcohol addition alkene reaction practice question

Hint: There is no given solvent, don’t make any assumptions 😉

How did you make out?

Compare your solutions to the answer key. Click the button below for details
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Comments

  1. Great practice, thank you Leah! You’re amazing! I would like to check my answers but the solutions have been taking a while to be sent. It is usual to take two hours?

  2. I wish I’d seen this earlier! I’ve got the gist of the mechanism but I always get confused with the little things and this cleared it up SO MUCH. Thank you!

  3. Thanks for putting this together, it’s really helpful. For question 6, I think OEt should have added since ethanol is used as nucleophile not water.

  4. can you please send the solutions to my email? can’t download it. Pleasssse leah

  5. Thank you!!! Your videos are sooo awesome! You saved me:)

  6. bhavya shah says:

    In Question 10 as six membered ring are more stable than seven membered ring (due to more angle strain in seven membered)the carbocation rearrangement results into hydrogen shift instead of ring expansion.Am I right?

    • Leah4sci says:

      6-member rings are more stable due to the ability to adapt a chair conformation and 109.5 degree bond angles

  7. jashwanth says:

    your explanations are awesome
    but where are solutions

  8. The videos i saw from you are the best, more then what my tutors gave and i really love it. you helped me alot thank you very much. By the way i’m from Papua New Guinea.

  9. where is the solution?

  10. Hi Leah, 1) Q12: Would we end up with a racemic product? 2) Q8: Is it possible to have a minor product formed (in addition to what you have shown) where the OEt adds meta to the crazy arm?

    • Did you download the solutions Jen?

      • Yes. (Thank you!) I`m just wondering for Q12 and Q8, if it is possible to get some additional products. …basically I`m wondering if my ‘other’ answers could be right as well 😉

  11. hi maam, i would just like to comment on the solutions you made particularly to the answer of question #6. Since it is an alkoxymercuration therefore the answer would be an ether. Maybe it is only a typo error but it is better to correct it in order to avoid confusion. Anyways, thank you for all the hard work. 🙂

  12. How do I check the solutions

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