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SN1 SN2 E1 E2 Practice Problem Orgo Quiz

April 1, 2019 By Leah4sci 100 Comments

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

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?

Send Me The Solutions

Filed Under: Organic Chemistry Practice Problems Tagged With: orgo quiz, quiz, SN1 SN2 E1 E2, substitution elimination

Comments

  1. Stephanie D Contois says

    July 15, 2019 at 1:38 pm

    Could you explain the reasoning behind the order for question #3? For an SN2 reaction, reactivity increases from methyl, to a primary, then a secondary, correct? Also, for question #2, although it’s an E1 this time, the reactivity still increases from methyl, to a primary, then a secondary.

    Reply
  2. Ara Galang says

    June 17, 2019 at 8:26 am

    For question 10, could you add the double bond to the other side since it is disubstituted instead of monosubstituted (following Zaitsev’s rule)?

    Reply
  3. Elise says

    June 7, 2019 at 12:50 pm

    Hello!
    I was just wondering why, in question 11, only the E2 product was present, and not the SN2 as well since OH- is both a strong nucleophile and base.
    Thanks!

    Reply
  4. Divyansh Agarwal says

    May 29, 2019 at 10:49 am

    First product would be the major product in question 17 as per your solution??

    Reply
    • Divyansh Agarwal says

      May 29, 2019 at 10:54 am

      Do you have a hard quiz than this

      Reply
  5. Terese says

    April 28, 2019 at 7:20 pm

    Sorry, I’m a bit confused for qn 6 as well… why the SN2 product minor and the E2 product major?

    Reply
  6. Terese says

    April 28, 2019 at 7:13 pm

    Hi Leah, for question 2 why is it that branching at the beta carbon slows down the E1 reaction? Same for question 3, why does the branching slow down the SN2 reaction?

    Reply
  7. debbie says

    April 9, 2019 at 12:33 pm

    hi would you please let me know how can I check the answers with you

    Reply
  8. Jahid Sardar says

    March 9, 2019 at 12:06 am

    Thank you so much mam ❤️❤️for helping us without any reason

    Reply
  9. muhammad junaid says

    February 16, 2019 at 11:34 am

    mam i cannot get these solution on email..is there is any other way in which i got these solution.

    Reply
  10. shaked says

    January 18, 2019 at 8:26 am

    HI Leah
    ques 20- why the ethyl isnt dash ? the iodo is number 1 than carbon3 is number 2 ,what makes it S. no?

    Reply
  11. Casey says

    December 1, 2018 at 5:38 am

    Solutions are deleted? Can’t find em

    Reply
  12. Colin says

    November 29, 2018 at 6:38 am

    I think the answer of number 11 is trans(E)-form, but not cis(Z)-form. From Newman projection, there are two products, and the transform is major product.

    Reply
  13. Jenn says

    November 27, 2018 at 5:04 pm

    On #2, why does the secondary rank higher than the secondary to tertiary rearrangement?

    Reply
  14. Madison K says

    November 20, 2018 at 1:58 pm

    Hi Leah,

    Im a bit confused on how number 17 worked. Can you explain

    Reply
  15. Muhammad Azhan says

    November 4, 2018 at 11:54 am

    Hi I don’t get the answeres via email

    Reply
  16. saqib says

    November 3, 2018 at 1:26 pm

    what is the major product in qn 17

    Reply
  17. saqib says

    November 3, 2018 at 1:15 pm

    In qn no. 11 product should be trans

    Reply
  18. Alejandro says

    November 1, 2018 at 9:29 pm

    Hello Leah, how can I get a better score for my next exam for organic chemistry which is going to be over Mechanism?Thanks

    Reply
  19. thebargle says

    October 28, 2018 at 8:41 pm

    Hi Leah, thanks for the quiz! For number 12, wouldn’t it be and E2 and SN2 product, not just E2?

    Reply
  20. monika says

    October 26, 2018 at 7:31 am

    I don’t get answers

    Reply
  21. ANURAG says

    October 23, 2018 at 6:15 am

    very nice examples…question 19 is confusing

    Reply
  22. Valery Medina says

    June 12, 2018 at 1:20 pm

    Hi Leah, could you possibly explain question 12 and 13. How come its an E2 reaction only and not an SN2? And for 13 why are the methyls dissociated?

    Reply
  23. PAUL ZIMBA says

    May 21, 2018 at 9:42 am

    Thank you ever so much Leah.

    Reply
  24. Anam Atiq says

    May 12, 2018 at 3:37 am

    Leah mam how could i get answers of above question?

    Reply
  25. Anam Atiq says

    May 12, 2018 at 3:36 am

    Leah mam how could i get answers of above questions?

    Reply
  26. amer says

    May 3, 2018 at 4:05 pm

    i like what you doing in organic chemistry it helps me alot to understand it.

    Reply
  27. charles says

    April 7, 2018 at 12:22 pm

    can you explain question 8, how come there wasn’t a hydride shift ?

    Reply
  28. R says

    March 24, 2018 at 2:11 pm

    thx a lot but can you explain Q4 because in solutions u wrote the final answer without explanation??

    Reply
  29. Chimwemwe january says

    February 19, 2018 at 10:53 am

    So nice

    Reply
  30. Chimwemwe january says

    February 19, 2018 at 10:52 am

    Can I get the answers pliz

    Reply
  31. Iris says

    February 17, 2018 at 11:45 pm

    is it possible to draw out the mechanism on the solution? because I dont understand for #6 why E2 is a major product, #14 why is it E2 not Sn2, and, #15 I cannot follow how you got an oxolane product…

    Reply
  32. tere says

    January 15, 2018 at 3:37 pm

    Why in question 7 does the cyanide group become equatorial? Shouldn’t it remain in the axial position?

    Reply
  33. Mashael says

    December 16, 2017 at 7:43 am

    The solutions don’t find in email? Why?

    Reply
  34. Emmanuel says

    December 10, 2017 at 1:51 pm

    That is good.

    Reply
  35. Garalt says

    November 18, 2017 at 2:45 pm

    Hello! I have a question about number 5, but I’m going to explain my process first:

    Br is on a primary carbon, so it is either E2 or SN2
    CH3O^- is a good base (I think)

    E2 needs a good base, and we have one

    HOWEVER, it goes through an SN2 because I can’t find a structure after an E2 that’s neutral… am I missing something or overthinking this?

    Thank you for providing this recourse 🙂

    Reply
  36. lsteels says

    November 15, 2017 at 11:52 pm

    Can you explain problem 17? No idea how you got that answer

    Reply
  37. Danielle says

    November 11, 2017 at 6:06 pm

    For question 11, is it not an E1 reaction since its 3rd degree Leaving group? To which, if it is E1, it wouldn’t matter if the hydrogen was anti periplanar (anti coplanar).

    Reply
  38. Entena Emedwin says

    October 29, 2017 at 2:03 am

    Hi I can’t get the answers via email and I really need them

    Reply
  39. Beth says

    October 24, 2017 at 10:46 pm

    Why wouldn’t question 8 have two products because it is tertiary to would react via SN1, so would have cis and trans as products? (Answer key only has only product)

    Reply
  40. karen says

    October 24, 2017 at 8:09 pm

    hi thanks so much for these! I just have a question about number 12, how come elimination is the major product? wouldn’t it be sn2 because its a strong base attacking a secondary carbocation?

    Reply
  41. Mahesh Meghraj says

    September 13, 2017 at 6:46 pm

    Thank you

    Reply
  42. sabrina says

    July 2, 2017 at 6:14 am

    Hi Ms. Leah! The link in my e-mail isn’t working. Do you mind checking it again? 🙂

    Reply
  43. Kaka Mlay says

    May 20, 2017 at 7:42 am

    E1 requires two steps while E2 requires only one step is it????

    Reply
  44. Sparsh Agarwal says

    May 2, 2017 at 5:55 am

    questions were nice,would love to see some questions of these rxns with stereochemistry at its peak,but where are the video solns??

    Reply
  45. Akshansh says

    May 1, 2017 at 5:14 am

    Thank you very much mam! It was a much needed help!

    Reply
  46. Umniyah says

    April 14, 2017 at 1:48 pm

    I didn’t get the answers although inhave send u an email

    Reply
  47. Alexis says

    March 29, 2017 at 2:12 pm

    Why is E2 favored in number 6 if its a strong nucleophile and will attack easily?

    Reply
  48. Lovely jessica says

    February 18, 2017 at 10:56 pm

    Hello, would you mind emailing me the solutions for the problems? i did not receive it even after signing up with two different emails.
    BTW you are really helping me with those YouTube videos and cheat sheets. ugh my prof is a nightmare 🙁 .

    Reply
  49. Demeke says

    January 9, 2017 at 5:36 pm

    I wish you mentioned what types of reaction ( Sn1, SN2, E1, or E2) each reaction went through in the answer section.

    Reply
  50. yasi says

    January 1, 2017 at 12:02 pm

    as i have exam on tuesday , i do not have so much time to answer each question by myself so i would be pleasant ,send me the solution of question.thank you so much.

    Reply
  51. yasi says

    January 1, 2017 at 10:13 am

    hello Ms leah, thank you for uploading useful video.I need the solution of these problems because i feel some problem to solve them.

    Reply
  52. Leah4sci says

    December 29, 2016 at 5:04 pm

    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.

    Reply
  53. Ipek Basaran says

    December 27, 2016 at 7:08 am

    I also dont understand why in Q 22 there is no Hydrideshift so the + goes to the bridge Carbon and gives a tertiary C+ so OH is adding there.

    Reply
  54. Ipek Basaran says

    December 27, 2016 at 5:32 am

    Hi Leah, I dont understand why in Q1 CH3CO2H is weaker than CH3OH , I thought resonance makes the NU stronger?

    Reply
  55. latihtubiusm says

    December 19, 2016 at 1:18 pm

    Thank you so much Leah! <33
    I do have a question though. Can you explain a bit about question no 4. Is it going to the left because iodide is a good leaving group (weak nucleophile as well) since it is in a polar aprotic solvent? while vice versa in polar protic solvent? Can I take it as that's the case?

    Reply
  56. Francys says

    December 19, 2016 at 12:18 pm

    Hey Leah, these problems are great. I have a question about the answer to problem 22. Wouldn’t Sn1 cause a hydrogen shift so that the carbocation could be on the more stable tertiary carbon? I did 2 Sn2 reactions in order to invert the stereochemistry instead. Could this be done?

    Reply
  57. Shriya Patel says

    December 1, 2016 at 1:43 am

    Can you go over #15? I’m not sure how the intermolecular Sn2 works and how we create the ring

    Reply
  58. Richard says

    November 23, 2016 at 6:03 am

    leah, those problems are fine. I will try them out. Hopefully I can get the solutions to compare with my answers

    Reply
  59. Andriana Snyder says

    November 21, 2016 at 4:45 pm

    For number 10 why does the double bond form at the end? Would it not form between the two carbons rather than just the one?

    Reply
  60. Melanie says

    November 20, 2016 at 11:22 pm

    I have an exam on this in 10 days, and I do not understand the material AT ALL, any suggestions on how to “cram” in order to pass this test? Thank you

    Reply
  61. Olivia Lee says

    November 14, 2016 at 2:19 pm

    I found this SOO helpful, thank you so much!!

    Reply
  62. Brian Blair says

    November 12, 2016 at 6:50 pm

    What does “CONC” mean??

    Reply
  63. Monish says

    November 3, 2016 at 3:50 pm

    Thank you so much mam

    Reply
    • Leah4sci says

      December 29, 2016 at 5:22 pm

      You’re welcome, Monish!

      Reply
  64. Steve says

    October 29, 2016 at 2:05 pm

    Why does reaction #10 produce an alkene monosubstitute? Would it not produce the Zaitsev product, the alkene disubstitute?

    Reply
  65. Mehak says

    June 18, 2016 at 1:01 pm

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

    Reply
    • Leah4sci says

      June 21, 2016 at 10:26 pm

      Try signing up again

      Reply
  66. Hoeun Lee says

    April 29, 2016 at 7:38 pm

    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.

    Reply
    • Leah4sci says

      May 3, 2016 at 8:51 am

      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

      Reply
      • jenn says

        November 26, 2016 at 11:29 pm

        i learned that a good nucleophile is small and negatively charged (oversimplifying) but still, i also listed O as a better nucleophile vs S given this question. Can you explain why larger is better?

        Reply
      • Jane Green says

        January 12, 2017 at 5:20 am

        I am confused too. We are mentioning the solvent because nucleophilicity differs in an aprotic solvent (same as basicity, the strength of the nucleophile increasing up the group or family) versus a protic solvent (opposite of basicity, the strength of the nucleophile decreasing down the group or family). It seems impossible to answer this question without mentioning the type of solvent, aprotic or protic.

        Reply
      • Gamma Girl says

        January 12, 2017 at 3:27 pm

        I am confused by question 1. Nucleophilicity differs in a protic versus an aprotic solvent. In an aprotic solvent, nucelophilicity increases going down a column. In a protic solvent, nucleophilicity increases going up a column. Question 1 should state the solvent, but the given answer follows a polar protic solvent. Do you agree, Leah?

        Reply
  67. natalie says

    April 26, 2016 at 4:56 pm

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

    Reply
    • Leah4sci says

      May 3, 2016 at 8:46 am

      Email me Natalie

      Reply
  68. Yossi Sourugeon says

    April 24, 2016 at 1:34 pm

    can someone explain me question 13?

    Reply
    • Leah4sci says

      May 3, 2016 at 8:55 am

      Did you check the solutions Yossi?

      Reply
  69. Abdul says

    March 25, 2016 at 5:26 pm

    For question 3, i got confused between 2,3. The double bond would not favor the SN2 reaction. Therefore, i thought the one without the double bond will be more reactive.

    Reply
  70. jay says

    March 22, 2016 at 8:25 am

    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

    Reply
    • Leah4sci says

      April 4, 2016 at 5:50 pm

      Jay: Email me if you still haven’t received the solutions

      Reply
      • ahmed asaa says

        October 31, 2018 at 1:45 pm

        Can I get the answers ,please?

        Reply
      • ahmed asaa says

        October 31, 2018 at 1:47 pm

        Can I get the answers, please?

        Reply
  71. enida says

    January 30, 2016 at 10:39 am

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

    Reply
    • Leah4sci says

      February 8, 2016 at 9:51 pm

      If you signed up you should have received them within 5 minutes Enida

      Reply
  72. Steven says

    December 11, 2015 at 9:21 am

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

    Reply
    • Leah4sci says

      December 16, 2015 at 10:38 am

      Steven, Error on my part. thanks for pointing it out

      Reply
  73. ghulam mohiuddin says

    December 1, 2015 at 9:22 am

    Good Leah you are beautiful

    Reply
  74. Zach says

    November 30, 2015 at 9:52 pm

    why is question 20 not an E2 reaction?

    Reply
    • Leah4sci says

      December 6, 2015 at 5:25 pm

      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

      Reply
  75. Erika says

    November 18, 2015 at 10:08 pm

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

    Reply
    • Leah4sci says

      November 23, 2015 at 2:40 pm

      It’s free. Did you get the email?

      Reply
  76. Erik says

    August 5, 2015 at 7:54 pm

    Since there are 2 anticoplanar beta-hydrogens to choose from in question 6, wouldn’t we expect 4 elimination products? (i.e. the cis/trans isomers resulting from the double bond at both positions)

    Reply
  77. Ali hayek says

    June 27, 2015 at 3:55 am

    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

    Reply
    • Leah4sci says

      July 1, 2015 at 6:41 pm

      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

      Reply
  78. michell says

    May 5, 2015 at 10:07 pm

    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.

    Reply
    • Leah4sci says

      May 7, 2015 at 6:54 pm

      That’s awesome Michell. There are a few mistakes which I plan to correct shortly

      Reply
  79. Danielle says

    April 30, 2015 at 4:04 pm

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

    Reply
    • Leah4sci says

      May 2, 2015 at 3:08 pm

      Thanks Danielle! Glad you found it helpful

      Reply
  80. Ahmed Tamer says

    April 27, 2015 at 1:54 pm

    Thank you so much Leah

    Reply
    • Leah4sci says

      April 28, 2015 at 11:11 am

      Thank you Ahmed. did you find it easy or difficult?

      Reply

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