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 … .. shown below. Give a mechanism by which it is formed and give the name of this mechanism. CH 3 CH 3 2) Provide the structure of the major organic product in the following reaction. CH 3 H Br D Na OCH 3 CH 3 OH 3) Provide the structure of the major organic product from following reaction. Na OCH 3 CH 3 OH Br H CH 3 H 4) Which diastereomer of …

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. CH 3 CH 3 2) Provide the structure of the major organic product in the following reaction. CH 3 H Br D Na OCH 3 CH 3 OH 3) Provide the structure of the major organic product from following reaction. Na OCH 3 CH 3 OH Br H CH 3 H 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 H 3 C Br KI 6) When 1-iodo-1-methylcyclohexane is treated with NaOCH 2 CH 3 as the base, the more highly substituted alkene product predominates. When KOC(CH 3 ) 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 CH 3 11) Give the major product and the mechanism of the following reaction. Ph Ph H 3 C H Br Na OCH 3 CH 3 OH 12) Predict the most likely mechanism and the product for the reaction below. Na OCH 3 CH 3 OH H 3 C Cl H 3 C 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) Which of the following mechanisms feature carbocation intermediates? A) S N 1 only B) S N 2 only C) E1 only D) E2 only E) both S N 1 and E1 16) Which mechanism(s) give(s) alkenes as the major products, Sn1, Sn2, E1, or E2? 17) Which compound produces only one alkene when treated with sodium methoxide? A) 2-chloro-2-methylpentane B) 3-chloro-3-ethylpentane C) 3-chloro-2-methylpentane D) 2-chloro-4-methylpentane E) 2-chloro-3-ethylpentane 18) When 3-iodo-3-ethylpentane is treated with sodium methoxide in methanol, the major organic product is an ______ that is generated through an ______ mechanism. A) ether, S N 1 B) ether, S N 2 C) ether, E1 D) alkene, E2 E) alkene, E1 ….

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