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Organic Chemistry: Review of Organic 4

Substitution and Elimination Review Test


Further Reading

1. The rate law shows:

2. Which of the following is the best leaving group?

3. In the E2 reaction, which of the following donates into the C-LG antibond?

4. A SN2 reaction will be fastest in which of the following solvents?

5. A SN1 reaction proceeds with

6. In order for a E2 reaction to take place, which of the following must be present?

7. Choose the most stable olefin

8. If SN2 reactions occurred through frontside attack, there would be

9. Predict the product

10. Which of reaction mechanism will dominated for this reaction?


X + Y → Z    

The rate law of the above reaction is:

rate = k [X]2 [Y]1    

What is the overall order of this rate law?

12. The E2 mechanism is

13. Why will this molecule not undergo an E2 elimination?

14. A polar, aprotic solvent favors which mechanism most?

15. What is the rate-limiting step of the E1 mechanism?

16. Which of the following is a polar, aprotic solvent?

17. What is the predominant E2 product?

18. Which of the following is the best description of the E2 reaction?

19. SN2 reactions generally proceed with

20. What is the major elimination product of this reaction?

What is the most reasonable reaction mechanism?

Can this molecule undergo an E2 reaction?

23. SN2 reactions are favored by

24. Which one of the following bases is best suited for the E2 reaction?

Choose the most energetically stable E2 product.

26. An increase in a transition state's energy necessarily requires

What will be the absolute stereochemistry of the product?

28. After elimination, which of the following will form the most stable alkene?

How many β -hydrogens are there on this molecule?

30. How many of these β -hydrogens are antiperiplanar to the C-LG bond?

31. Predict the E2 elimination product.

32. Choose the most stable carbocation

Predict the most stable carbocation intermediate formed after LG leaves.

34. Predict the product

35. All other things being equal, a SN1 reaction will be fastest in which solvent?

This molecule does not undergo SN2 attack. Choose the best explanation.

Molecule A is formed through a SN2 reaction. Which pair of reactants would give the highest yield of molecule A?

38. The activation energy of concerted reaction A is twice that of concerted reaction B. Which of the following must be true?

Why is this molecule not a good candidate for E1 ?

40. Which of the following is the best nucleophile?

41. Which of the following is the best leaving group?

42. Which of the following will promote the fastest E1 / SN1 reaction?

43. Assuming no rotation about the C-C bond, which of the following pairs is antiperiplanar?

44. Choose the polar, protic solvent

Choose the most abundant E2 product

Predict the stereochemistry of the E2 product. (Hint: try rotating the C-C bond)

47. If the previous molecule is subjected to E1 conditions, what will be the stereochemistry of the most energetically stable product?

This molecule could be the product of only

X is thought to substitute for Br with a frontside attack mechanism. Predict the probably absolute stereochemistry of the product. Assume that X has the same CIP priority as Br.

Predict the major SN2 product.