TAILIEUCHUNG - ORGANIC CHEMISTRY I – PRACTICE EXERCISE

This is a dangerous combination. The persistence and mobility of POPs means that they are literally everywhere in the world, even in the Arctic,Antarctica, and remote Pacific islands. Their attraction to fatty tissue, known as "bioaccumulation", means that even though a poison is first dispersed widely and thinly it gradually starts to concentrate as organisms consume other organisms as they move up the food chain. The chemicals reach magnified levels – up to many thousands of times greater than background levels – in the fatty tissues of creatures at the top of the food chain, such as fish, predatory birds, and mammals, inclu- ding human beings | ORGANIC CHEMISTRY I - PRACTICE EXERCISE Elimination Reactions and Alkene Synthesis 1 One of the products that results when 1-bromo-2 2-dimethylcyclopentane is heated in ethanol is shown below. Give a mechanism by which it is formed and give the name of this mechanism. CH3 3 CH3 2 Provide the structure of the major organic product in the following reaction. CH3 NaOCH3 r ch3oh H D 3 Provide the structure of the major organic product from following reaction. H NaOCH3 H à Br Ch3 ch3oh 4 Which diastereomer of 1-bromo-4-t-butylcyclohexane the cis or the trans undergoes elimination more rapidly when treated with sodium ethoxide Explain your answer. 5 Provide the structure of the major organic product from the following reaction. Br KI Br 6 When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 as the base the more highly substituted alkene product predominates. When KOC CH3 3 is used as the base the less highly substituted alkene predominates. Give the structures of the two products and offer an explanation. 7 Which of the following statements apply to E1 reactions of alkyl halides Choose as many as necessary. I. Rate k base II. Rate k base RX III. Rate k RX IV. The reactions occur in two or more distinct steps. V. Rearrangements are sometimes seen. 8 What is Saytzeff s rule 9 What major product results when 2-bromo-2-methylbutane is treated with sodium ethoxide. 10 How many distinct alkenes can result from E2 elimination of the compound below Give their structures and IUPAC names. I CH3 11 Give the major product and the mechanism of the following reaction. h3c h .Ph Pli Br NaOCH3 CH3OH 12 Predict the most likely mechanism and the product for the reaction below. NaOCH3 ------ CH3OH 13 Predict the most likely mechanism and the product from the reaction between 2-chloro-2-methylpentane and sodium ethoxide in ethanol. 14 The major product which results when 2-chloro-2-methylpentane is heated in ethanol is an ether. Show and name the mechanism by which this ether forms. 15

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