ochem homework
#1 Write a structural formula for 2,3-dimethyl-2-pentene (show stereochemistry as needed). Write a structural formula for (E)-2-pentene (show stereochemistry as needed). Write a structural formula for 3-methylcyclobutene (show stereochemistry as needed). Write a structural formula for (Z)-3-hexene (show stereochemistry as needed). Write a structural formula for (E)-4-methylhex-4-en-1-yne (show stereochemistry as needed). #2 Give the IUPAC names for each of the following: #3 When trans-2-methylcyclohexanol (see the following reaction) is subjected to acid-catalyzed dehydration, the major product is 1-methylcyclohexene: However, when trans-1-bromo-2-methylcyclohexane is subjected to dehydrohalogenation, the major product is 3-methylcyclohexene: Account for the different products of these two reactions. Dehydration of trans-2-methylcyclohexanol is: an E1 reaction, and must proceed through formation of a carbocation intermediate. an E2 reaction, and must proceed through an anti coplanar transition state. an E1 reaction, and must proceed through an anti coplanar transition state. an E2 reaction, and must proceed through formation of a carbocation intermediate. This leads to the more or less stable alkene. Dehydrohalogenation of trans-1-bromo-2-methylcyclohexane is: an E2 reaction, and must proceed through formation of a carbocation intermediate. an E2 reaction, and must proceed through an anti coplanar transition state. an E1 reaction, and must proceed through an anti coplanar transition state. an E1 reaction, and must proceed through formation of a carbocation intermediate. This leads to the more or less stable alkene. #4 Draw the major and minor product when the following alkyl halide is heated with sodium ethoxide in ethanol. You may neglect cis-trans isomerism of the products when answering this question. If there is only one product, click "No Reaction" for the minor product. The minor product is: The major product is: #5 Draw the major and minor product when the following alkyl halide is heated with sodium ethoxide in ethanol. You may neglect cis-trans isomerism of the products when answering this question. If there is only one product, click "No Reaction" for the minor product. The minor product is: The major product is: #6. Draw the major and minor product when the following alkyl halide is heated with sodium ethoxide in ethanol. You may neglect cis-trans isomerism of the products when answering this question. If there is only one product, click "No Reaction" for the minor product. The minor product is: The major product is: #7. Draw the major and minor product when the following alkyl halide is heated with sodium ethoxide in ethanol. You may neglect cis-trans isomerism of the products when answering this question. If there is only one product, click "No Reaction" for the minor product. The minor product is: The major product is: #8 Draw the major and minor product when the following alkyl halide is heated with sodium ethoxide in ethanol. You may neglect cis-trans isomerism of the products when answering this question. If there is only one product, click "No Reaction" for the minor product. The minor product is: The major product is: #9 a . Draw the products of the reaction between the following haloalkane and t-BuOK/t-BuOH Draw Major and Minor product of the reaction b. Draw the products of the reaction between the following haloalkane and t-BuOK/t-BuOH Draw Major and Minor product of the reaction C. Draw the products of the reaction between the following haloalkane and t-BuOK/t-BuOH Draw Major and Minor product of the reaction D. Draw the products of the reaction between the following haloalkane and t-BuOK/t-BuOH Draw Major and Minor product of the reaction E. Draw the products of the reaction between the following haloalkane and t-BuOK/t-BuOH Draw only product of the reaction #10 A methanide shift occurs. The required anti coplanar transition state leads to only the given product. The alternative product could only be produced from an unstable conformation. A hydride shift occurs. A methanide shift occurs. The alternative product could only be produced from an unstable conformation. The required anti coplanar transition state leads to only the given product. A hydride shift occurs. The alternative product could only be produced from an unstable conformation. A methanide shift occurs. A hydride shift occurs. The required anti coplanar transition state leads to only the given product. A methanide shift occurs. A hydride shift occurs. The alternative product could only be produced from an unstable conformation. The required anti coplanar transition state leads to only the given product. #11. Draw the major or only product that would be formed when the following alcohol is subjected to acid-catalyzed dehydration. Indicate whether this is the major product or the only product of the reaction. Draw the product that would be formed when the following alcohol is subjected to acid-catalyzed dehydration. If more than one product would be formed, draw the major product and indicate whether this alkene is the major product or the only product of the reaction. (Neglect cis-trans isomerism.) Draw the product that would be formed when the following alcohol is subjected to acid-catalyzed dehydration. If more than one product would be formed, draw the major product and indicate whether this alkene is the major product or the only product of the reaction. (Neglect cis-trans isomerism.) #12 Select the products that would be formed when the following alcohol is subjected to acid-catalyzed dehydration. If more than one product would be formed, designate the compound that would be the major product. (Neglect cis-trans isomerism.) The product(s) is(are): The major product is: (if there is only one product, select it) #13. Outline a synthesis of propene from each of the following: Propyl chloride Propyl chloride propene b) Isopropyl chloride Isopropyl chloride propene (c) Propyl alcohol Propyl alcohol propene d ) Isopropyl alcohol Isopropyl alcohol propene (e) 1,2-Dibromopropane 1,2-Dibromopropane propene f) Propyne Propyne propene #14 tarting with an appropriate alkyl halide and base, outline the synthesis that would yield the following alkene as the major (or only) product. Draw the alkyl halide reactant. Select the proper base: Starting with an appropriate alkyl halide and base, outline the synthesis that would yield the following alkene as the only product. Draw the alkyl halide reactant. Select the proper base: Starting with an appropriate alkyl halide and base, outline the synthesis that would yield the following alkene as the only product. Draw the alkyl halide reactant. Select the proper base: