SN1 SN2 E1 E2 Practice Problem Orgo Quiz

Substitution Elimination Reactions Tutorial Video SeriesSubstitution and Elimination reactions are potentially the most difficult concepts covered at the Organic Chemistry 1 level. In addition to studying the SN1 SN2 E1 and E2 reaction mechanisms, you also have to understand the similarities and differences so that you can derive the correct products for specific reaction conditions.

I’ve put together this medium/tricky quiz to help you practice the reactions and gauge your level of comprehension.

Not fully confident yet? Go back and review my entire SN1 SN2 E1 E2 reaction video series and study the associated cheat sheet before getting started. So take your time as you go through the questions. If you get stuck just visit the video series page (linked above) and watch the related tutorial.

Download PDF Solutions posted at the end of the quiz.

Substitution Elimination Practice Problems

Question 1: Rank the following nucleophiles in order of increasing strength

Need help? Watch the Nucleophile vs Base videos in the series

SN1 SN2 E1 E2 Practice Problems with Solutions 1

Question 2: Arrange the following molecules in order of increasing reactivity/ability for a unimolecular elimination reaction. (E1)

SN1 SN2 E1 E2 Practice Problems with Solutions 2

Question 3: Arrange the following molecules in order of increasing reactivity to undergo a bimolecular substitution reaction (SN2)

SN1 SN2 E1 E2 Practice Problems with Solutions 3

Question 4: Which direction is favored at equilibrium when dissolved in an acetone solution? What about methanol?

Need help? see the solvents video in the series

SN1 SN2 E1 E2 Practice Problems with Solutions 4

Predict the product for each of the following reactions. Be sure to show stereochemistry when appropriate. Be sure to label major/minor products when more than one outcome is possible.

Question 5:

SN1 SN2 E1 E2 Practice Problems with Solutions 5

Question 6

SN1 SN2 E1 E2 Practice Problems with Solutions 6

Question 7

SN1 SN2 E1 E2 Practice Problems with Solutions 7

Question 8

SN1 SN2 E1 E2 Practice Problems with Solutions 8

Question 9

SN1 SN2 E1 E2 Practice Problems with Solutions 9

Question 10

SN1 SN2 E1 E2 Practice Problems with Solutions 10

Question 11

SN1 SN2 E1 E2 Practice Problems with Solutions 11

Question 12

SN1 SN2 E1 E2 Practice Problems with Solutions 12

Question 13

SN1 SN2 E1 E2 Practice Problems with Solutions 13

Question 14

SN1 SN2 E1 E2 Practice Problems with Solutions 14

Question 15

SN1 SN2 E1 E2 Practice Problems with Solutions 15

Question 16

SN1 SN2 E1 E2 Practice Problems with Solutions 16

Question 17

SN1 SN2 E1 E2 Practice Problems with Solutions 17

Question 18 Draw ALL possible starting haloalkanes that would form this product when undergoing unimolecular elimination.

SN1 SN2 E1 E2 Practice Problems with Solutions 18

Question 19: Show how to bring about the following transformation. You may use any reactants and reagents necessary

SN1 SN2 E1 E2 Practice Problems with Solutions 19

Question 20: Predict the product/s when (2R,3S) 3-ethyl-2-iodohexane reacts with NaSCH3 in dimethyl sulfoxide.

Question 21: Draw a complete mechanism for the following reaction. Be sure to include all intermediates, formal charges, and pushing arrows.

SN1 SN2 E1 E2 Practice Problems with Solutions 21

Bonus Question 22: Show how to bring about the following transformation. Hint: Pay attention to the orientation of substituents

SN1 SN2 E1 E2 Practice Problems with Solutions 22

Bonus Question 23: Show the complete mechanism for the following transformation. Hint: More than one reaction is required.

SN1 SN2 E1 E2 Practice Problems with Solutions 23

 

What did you think of this quiz? Easy? Hard? Need more practice?
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Comments

  1. hello ! I can’t get the answers via email. Thank you in advance !

    • Hi Frida, if the solutions don’t come to the email you entered, try looking in the spam folder or maybe try entering in a different email.

  2. Thank you so much mam

  3. I m unable to get solutions..i filled the details but didnt receive the mail

  4. Hoeun Lee says:

    Ms. Leah, can you please explain number 1? Why is NaSCH3 stronger than NaOCH3? I watched your video again and again, but isn’t the answer different from protic to aprotic? If it is protic, Sulfur should be stronger than O but if aprotic, O is stronger than S? I am so confused…….does that question have to specify that or polar protic is given? Or am I not understanding something? And why is Carboxylic acid weaker than CH3OH?
    I’m so lost… please help.

    • Leah4sci says:

      I don’t understand why you’re asking about solvent here Hoeun. S is a stronger nucleophile compared to O due to its larger size

  5. could i get the answer to these the email didn’t come

  6. Yossi Sourugeon says:

    can someone explain me question 13?

  7. question 15 is quit tricky for me. I haven’t received the solutions yet so can anyone tell me how to go about it? How do you solve for the OH

  8. I’m not having the answers,can’t wait to see them….

  9. On question 1, how does NaSCH3 differ from CH3S? NaSCH3 should disassociate to Na+ and -SCH3. How come CH3S isn’t negatively charged?

  10. ghulam mohiuddin says:

    Good Leah you are beautiful

  11. why is question 20 not an E2 reaction?

    • negative sulfur makes a strong nucleophile but weak base. This means it prefers SN2 over E2. In addition, since the reaction takes place in a polar aprotic solvent, SN2 is favored once more over E2

  12. i can’t open the quiz solutions easily, i can’t open the link. idk if i need to pay something or?

  13. Ali hayek says:

    i do not understand why question Number 5 is an Sn2. the Nucleophile is strong but the solvent is polar and protic, which means Sn2 cannot happen, CH3O^- is a strong base so it will do E2, especially that the substrate is primary

    • Leah4sci says:

      It is not possible to form a pi bond on a primary benzyl carbon since the benzene ring is already maxed out with bonds and does not have a free hydrogen atom. This is a trick question because even though E2 would be most favorable the reaction proceeds SN2 as the less-likely but only possible option

  14. michell says:

    This quiz was about medium difficulty. I took it once and didn’t understand it. I studied for many hours and now I find it to be a medium difficulty.

  15. Danielle says:

    These are really helpful and sums up all we learned in the boot camp
    Thanks Leah!!!!

  16. Ahmed Tamer says:

    Thank you so much Leah

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