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Alkene Reaction Practice Problem Set

April 5, 2019 By Leah4sci 42 Comments

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

Send Me The Solutions!

Filed Under: Organic Chemistry Practice Problems Tagged With: alkene reaction practice questions, alkene reaction quiz, organic chemistry, organic chemistry practice

Comments

  1. Amila Skopljak says

    June 15, 2019 at 6:00 am

    Dear Leah, thank you! Your videos are soooo helpful, I wish you all the best in your life, you deserve it! I signed more times for the solutions and never got the mail, also for some cheat sheets, never got anything 🙁 I also check my spam folder but nothing there. Could you please send them to me? Thanks!

    Reply
  2. Mimi says

    March 24, 2019 at 3:28 pm

    Hey Leah for number 13, wouldn’t the Cl adds to the most substituted and H to the less substituted side? In your solution sheet has Cl adding to the less substituted side? Can you explain please!

    Reply
  3. Amanda says

    December 9, 2018 at 8:06 pm

    Thank you for this awesome quiz! For number 8, though, I think an ethyl shift could be done for a minor product

    Reply
  4. Jonathan Jonassaint says

    November 29, 2018 at 8:28 pm

    Hola, for question #4 I believe that halogenation is an anti addition so the Cl atoms would be on opposite faces one wedged one dashed not both dashed.

    Reply
  5. Fumito says

    October 26, 2018 at 2:49 am

    For Q13, are there no ortho- and para-substituted aromatic compounds? Because secondary benzyl carbocation has resonance structure, which positive charge locates in benzine.

    Reply
  6. Mahi says

    March 24, 2018 at 4:58 pm

    For Q.5 could the reagents also be 1.Hg(OAc)2, CH3OH and 2.NaBH4, H2O

    Reply
  7. Mimi says

    March 6, 2018 at 3:49 am

    Hi Leah! Your videos have all been a wonderful help!
    I was just wondering why in question 7 when we have the formation of a carbocation, is there not have a hydride shift (since there is a tertiary carbon next to the cation)?

    Reply
  8. Ravi Teja says

    December 24, 2017 at 10:54 pm

    Mam Can u tell me reason for 13 and 5

    Reply
  9. Ravi Teja says

    December 24, 2017 at 10:27 pm

    Can u help me in getting key

    Reply
  10. Alexia Markowski says

    December 1, 2017 at 10:14 pm

    the solutions aren’t sending to my email 🙁

    Reply
  11. faiz says

    May 8, 2017 at 10:00 am

    Hey Leah, I was looking at the solutions, and it says that #6 is an alkoxymercuration. The end result had an Oh, so why is it not an Oxymercuraton?

    Reply
  12. Anami Bhatt says

    March 29, 2017 at 8:51 pm

    Hi Leah,

    I am not able to download the solutions via the link. It is not working. Can you please email me the solutions?

    Reply
  13. Akash Yadav says

    March 21, 2017 at 1:06 pm

    In question no.6 how will we decide which group will leave in the last step of mechanism (i.e. ethyl or hydrogen ion forming a product which is alcohol or ether)??

    Reply
  14. Samiksha Sachdeva says

    March 19, 2017 at 5:18 pm

    Hey Leah! Thanks for this practice sheet.It was a challenging one.I guess that the answer to Q6 is given wrong.It should be OEt instead of OH.And I couldn’t get Q15 .Could you please explain it to me?

    Reply
  15. Muneer Al.moqbali says

    October 26, 2016 at 10:12 am

    also for Q13 there is something wrong

    Reply
  16. Muneer Al.moqbali says

    October 26, 2016 at 10:05 am

    the solution for Q9 is wrong

    Reply
  17. Holly says

    June 9, 2016 at 5:45 am

    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?

    Reply
    • Leah4sci says

      June 10, 2016 at 3:14 pm

      HOlly: Should have been instant. Sign up again if you still don’t have it

      Reply
  18. maria says

    April 30, 2016 at 5:27 pm

    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!

    Reply
    • Leah4sci says

      May 3, 2016 at 8:52 am

      Better late than never Maria. Glad to help

      Reply
  19. Wanda says

    April 18, 2016 at 10:28 pm

    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.

    Reply
    • Leah4sci says

      April 20, 2016 at 8:43 pm

      You’re correct Wanda, it’s a mistake on the key

      Reply
  20. Tiara says

    March 19, 2016 at 10:53 pm

    for number 6. How come the et group is not attached to the OH in the final product?

    Reply
  21. jaey says

    March 9, 2016 at 3:17 am

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

    Reply
    • Leah4sci says

      April 4, 2016 at 5:41 pm

      Email me Jaey

      Reply
  22. Liana says

    October 29, 2015 at 9:34 pm

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

    Reply
    • Leah4sci says

      October 31, 2015 at 6:24 pm

      Glad to help Liana

      Reply
  23. bhavya shah says

    July 15, 2015 at 12:23 pm

    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?

    Reply
    • Leah4sci says

      July 17, 2015 at 1:54 pm

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

      Reply
  24. jashwanth says

    June 27, 2015 at 11:52 am

    your explanations are awesome
    but where are solutions

    Reply
    • Leah4sci says

      July 1, 2015 at 6:39 pm

      Did you click the link at the bottom of the page?

      Reply
  25. kelly says

    May 12, 2015 at 5:24 am

    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.

    Reply
    • Leah4sci says

      May 12, 2015 at 9:49 pm

      Than you glad to help

      Reply
  26. Vincent says

    February 13, 2015 at 6:02 am

    where is the solution?

    Reply
    • Leah4sci says

      February 14, 2015 at 7:57 pm

      Vincent: There’s a link at the bottom for the solution set

      Reply
  27. Jen says

    December 27, 2014 at 7:06 pm

    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?

    Reply
    • Leah4sci says

      January 4, 2015 at 3:22 pm

      Did you download the solutions Jen?

      Reply
      • Jen says

        January 4, 2015 at 7:40 pm

        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 😉

        Reply
  28. Feldan says

    December 7, 2014 at 1:33 am

    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. 🙂

    Reply
    • Leah4sci says

      December 9, 2014 at 11:25 am

      Oh wow you are absolutely correct Feldan. I fell for my own trick!!!!! thanks for pointing it out

      Reply
  29. Dee says

    November 10, 2014 at 5:09 pm

    How do I check the solutions

    Reply
    • NiveNIVE says

      February 22, 2019 at 8:52 am

      I am not getting ans key it is taking lot of time but ur ques r very nice thanx mam

      Reply

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