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Part II. Nomenclature and Structures. (8 points) (1) Give the correct IUPAC name for each of the following structures compound I (II) Draw the structure that corresponds to each of the following names (a) (E)-2,4-dimethyl-3-hexene پر + HCI (step 1) Br Part III. Mechanisms 1. (6 points). In the following reaction of the addition of HCI to vinylcyclopentane (compound 1), one of the major products formed is 1-chloro-1-ethylcyclopentane (compound 2). The mechanism for this reaction involves the formation of intermediate A, which rearranges to intermediate B. The final product formed is compound 2. a. In the boxes, draw the structures of both carbocation intermediates A and B. H-Br draw arrows on these for the first step B. step 1 (step 2) (b) 4,4-dimethyl-2-hepten-5-yne intermediate A intermediate B b. Give a short explanation why the intermediate A rearranged to the intermediate B H 2. (4 points). The following is an electrophilic addition of HBr to ethylene. The reaction occurs in two steps and involves a carbocation intermediate. For each of these two steps, draw the curved arrows (on the species below) showing how the electrons move. H H CH3 ✦ Br draw arrows on these for the second step CH3 (step 3) step 2 compound 2
Dact II. Nomenclature and Structures. (points) (1) Cive the correct IUPAC name for each of the following structures (1) Draw the structure that corresponds to each of the following names (4) (E)-2,4-dimethyl-3-hexene compound 1 + Part III. Mechanisms 1. (6 points). In the following reaction of the addition of HC1 to vinyleyclopentane (compound 1), one of the major products formed is 1-chloro-l-ethylcyclopentane (compound 2). The mechanism for this reaction involves the formation of intermediate A, which rearranges to intermediate B. The final product formed is compound 2. a. In the boxes, draw the structures of both carbocation intermediates A and B. HCI (step 1) 2. (4 points). The following is an electrophilic addition of HBr to ethylene. The reaction occurs in two steps and involves a carbocation intermediate. For each of these two steps, draw the curved arrows (on the species below) showing how the electrons move. M draw arrows on these for the first step BL step 1 (b) 4,4-dimethyl-2-hepten-5-yne H (step 2) intermediate A intermediate B b. Give a short explanation why the intermediate A rearranged to the intermediate B . CH3 Br draw anows on these for the second step -CH3 step 2 (step 3) compound 2