1. Which of the following would enhance the rate of the E2 reaction over the SN2 reaction?

hydroxide

2. Nucleophilic substitution and elimination reactions often compete with one another. In general, which of the
following would enhance the rate of the E2 reaction over the SN2 reaction? Branching at the α or β carbon
3. Which of the following statements is NOT true of nucleophilic substitution reactions ?
*Equilibrium favors the products of the nucleophilic substitution when the leaving
group is a stronger base than the nucleophile.

*The charged carbon atom of a carbocation has a complete octet of valence shell electrons

4. *Rates of both SN1 and SN2 increases at higher temperatures (TRUE), the more elimination products you get.
*SN2 occurs with inversion of configuration (TRUE)
5. Which of the following statements regarding the E2 mechanism is wrong?

6. Ether molecules are polar, but do not form hydrogen bonds with other molecules because there is no hydrogen atom
bonded to the oxygen.
7. Which of the following is never a leaving group in a nucleophilic substitution reaction? Hydroxide/hydroxyl
8. The best way to prepare 1,2-Dibromoethane is to treat: Ethylene with Br2

9. KBr, on reaction with conc. H2SO4, gives reddish-brown gas which is: BROMINE
10. Which of the following factors influence whether a reaction will proceed by an SN1, SN2, E1, or E2 mechanism? All of these
11. Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide. SN2 and E2
12. How should CH3CHClCH2CH3 be classified? secondary alkyl halide
13. Which of the following is the best leaving group? Iodine
14. Isopropyl bromide reacts with alcoholic KOH (the solvent is an alcohol) to give propene
15. Which of the following halides is least reactive in an E2 reaction with sodium methoxide? (CH3)2CHCHICH3
16. Which of the following is the least reactive substrate in an E2 reaction? Compound I is least reactive towards E2 elimination
reactions as there must be at least one beta hydrogen present for the elimination of a HCl
17. Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-
pentene as the only alkene product? 3-chloropentane
18. Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide. SN2 and E2
19. Which of the following factors has no effect on the rate of SN1 reactions? The concentration of the nucleophile
20. 2-Bromobutane reacts alcoholic KOH to mainly give 1-Butene
21. A highly useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl
compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each alcohol
below. List all possibilities.
22. What alkyl halides might the following alkenes have been made from?

Alkenes can be generated from haloalkenes by elimination using a strong base. The elimination can be
either E1 or E2, depending upon the solvent used.