CHM2207-Worksheet 2
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Renee RamsarranCHM2207-Worksheet 2
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Renee RamsarranCHM2207 – Organic Chemistry 1 – Fundamental Mechanisms
Worksheet 2 -Topics covered in Hours 6 to 9
1. In a SN2 reaction are the nucleophile (Nuc) and the transition state polar or nonpolar?
2. Which solvent is best at stabilizing the nucleophile and transition state? Polar or Nonpolar?
3. Study Table 1 below and discuss the important factor(s) that can account for the order of reactivity
shown in the Table.
Table 1 Relative Rates of Reactions of Alkyl Halides in S N2 Reactions
Substituent Compound Approximate Relative Rate
Methyl CH3X 30
1o CH3CH2X 1
2o (CH3)2CHX 0.03
Neopentyl (CH3)3CCH2X 0.00001
3o (CH3)3CX ~0
4. A level 3 University student posited that the activation energy for an SN1 reaction of a simple methyl,
primary, or secondary halide, is so large, thus an SN1 reaction with a methyl, primary or secondary halide
does not compete with the corresponding SN2 reaction. Use Figure 1 and any associated postulate to
account for the student’s hypothesis.
Figure 1. The Free Energy Plot For Endergonic and Exergonic Reaction Steps
5. Rank the following in terms of decreasing nucleophilicity in methanol: CH3CO2-, CH3OH, CH3O-,
CH3CO2H, CN-
6. Classify the following solvents as being protic or aprotic: formic acid, HCO2H; acetone, CH3COCH3;
acetonitrile, CH3CN; formamide, HCONH2; sulfur dioxide, SO2; ammonia, NH3; trimethylamine, N(CH3)3;
ethylene glycol, HOCH2CH2OH
7. List two conditions that will favour an SN1 reaction.
8. Which SN1 reaction of each pair would you expect to take place more rapidly? Explain your answer.
1
(a)
(b)
9. Define the term stereospecific reaction.
10. Alkenes can be halogenation under various conditions. State the conditions for the formation of a
halohydrin as the major product.
11. Write the equation for the reaction of ethene with a halogen and water to give the major and minor
organic product and the inorganic product. Give the general name for the minor product formed.
12. Write the mechanism for halohydrin formation from an alkene.
13. Draw a mechanism for the following reaction when (HO-) is mixed with each of the following
compounds. Note you need to look for the most acidic proton in each case.
(a)
(b)
14. Predict the product(s) for the following reaction.
(a)
15. Which of the following compounds is more acidic? Explain.
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16. Rank the following in terms of decreasing nucleophilicity in methanol: CH3CO2- CH3O- CH3S- CH3SH
CH3OH
17. Write the following as net ionic equations and designate the nucleophile, substrate, and leaving
group in each reaction:
18. There are four compounds with the formula C4H9Br. List them in order of decreasing reactivity in an
SN2 reaction. (Sol Quiz6_6.4)
19. Predict the missing reactants, reagents, intermediates, or products.
20.
