Alkenes: Common Exam Problems (With Solutions)

by James

Preparing for an upcoming midterm or exam on alkenes? 
On this page you’ll find 20 typical exam problems, roughly ordered by level of difficulty. Underneath each problem there is a video which describes the thought process behind solving the problem in detail. 
It’s impossible to provide a list of problems that will anticipate *every* type of potential problem you’ll get on an exam. But this contains many “instructor’s favourites” found at a wide variety of schools. It’s intended to help you prepare and also to learn how to solve these types of problems. 

I strongly advise you try to solve each problem *on your own* before watching the videos. You’ll get a lot more out of it that way. 

Additional resources:

Note that your specific course might differ in which reactions are taught and in several other subtle respects. The concepts taught are very general, but there can be small differences with the presentation. 

List Of Problems

  1. Alkene stability
  2. Draw the products
  3. Draw the products (2) – what type of isomers?
  4. Draw the products (3) – identify it if drawn as a Fischer projection?
  5. Draw the products (4) – can you identify it if drawn as a cyclohexane chair?
  6. Draw the products (5) – which one is incorrect? 
  7. Draw the products (6) – applying nomenclature
  8. Ozonolysis (1)
  9. Intramolecular reactions (1)
  10. Rearrangement mechanism (1)
  11. Rearrangement mechanism (2)
  12. Apply the key concepts to a new reagent 
  13. Given reactants and products, identify reagents
  14. Identify the right reagent
  15. Think backwards: which alkene would give this product? (multiple choice)
  16. Think backwards: which alkene would give this product?
  17. Draw the products (7) – what type of isomers?
  18. Ozonolysis (2)
  19. Intramolecular reactions (2)
  20. Bicyclic Alkene – Intramolecular Reaction


1. Alkene stability [back to top]


2. Draw The Products (1) [back to top]


3. Draw The Products (2) – What Type Of Isomers? [back to top]

4. Draw The Products (3)  Fischer Projection [back to top]

5. Draw products (4)  Cyclohexane Chair [back to top]

6. Draw The Products (5) – Which One Is Incorrect? [back to top]

7 – Draw The Products (6) – Applying Nomenclature [back to top]


8. Ozonolysis (1) [back to top]

9. Intramolecular Reactions (1) [back to top]

10. Rearrangement Mechanism (1) – [back to top]

11. Rearrangement Mechanism (2) – [back to top]


12. Apply concepts to an unfamiliar reagent [back to top]




13. Given Reactants and Products, Identify Reagents [back to top]


14. Identify The Correct Reagent [back to top]

15. Think Backwards: What Alkene Would Give This Product [back to top]

16. Draw The Right Starting Alkene [back to top]




17. Draw the products – identify the relationships [back to top]

18. Ozonolysis (2) – Thinking Backward [back to top]


19. Intramolecular reaction (2) [back to top]

20. Bicyclic Alkene, Intramolecular Reaction [back to top]


{ 1 comment… read it below or add one }

Kelsey Halstead

Hi James,
I understand how you drew number 7, but I drew it a bit differently. On carbon six I have my methyl group on a wedge and hydrogen on a dash but it is oriented so that it is (R), because I drew it below the ethyl instead of above. Does this mean it is the wrong way to draw it? Also, when drawing the enantiomer, would I also have to account for the opposite configuration for the adjacent methyl stereocenters? Thank you for your time.
file:///Users/Kelsey/Desktop/Screen%20Shot%202015-04-07%20at%204.26.19%20PM.png I tried to get a screenshot of it but I don’t think it will allow another user access.


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