Lesson 5 Problems

1. Arrange the following nucleophiles in order of increasing nucleophilicity Ethoxide, hydroxide, water and amide ion 2. Arrange the following leaving groups in order of increasing stability Chloride, fluoride, bromide, hydroxide, water 3. Predict whether each of the reactions below will run by an SN1 or SN2 mechanism a) b) c) d) Potassium hydroxide reacting with methyl chloride Sodium amide reacting with ethyl bromide Ammonia reacting with t-butyl iodide Ethanol and isopropyl iodide

4. Phosphoric acid can be used to protonate alcohols, creating a situation with a good leaving group on a secondary carbon, but no nucleophile. Then 3-pentanol is mixed with phorphoric acid, what product is expected to form?

5. When cyclohexyl chloride is mixed with sodium methoxide, cyclohexene is produced. Draw a mechanism for this reaction.

6. When (2S, 2R)-2-bromo-34-methylpentane reacts with methoxide ion, only one of the two possible isomers forms. Circle the isomer which forms and explain this observation.