_alkene

_alkene Foundation of Organic Chemistry Fall 2015 Homework 6 (CH7_alkene) Name___________________________________ MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) What two atomic orbitals or hybrid atomic orbitals overlap to form the C??H bond in ethylene? 1) A) C sp3 + H s B) C sp2 + H s C) C p + H s D) C sp + H s 2) Consider molecules with the formula C10H16. Which of the following structural features are not possible within this set of molecules? 2) A) 3 double bonds B) 1 ring and 1 triple bond C) 2 rings and 1 double bond D) 2 triple bonds E) 2 double bonds and 1 ring 3) How many elements of unsaturation are implied by the molecular formula C6H12? 3) A) 0 B) 1 C) 2 D) 3 E) 4 4) How many elements of unsaturation are implied by the molecular formula C7H11Cl? 4) A) 0 B) 1 C) 2 D) 3 E) 4 5) The steroid testosterone has the molecular formula C19H28O2. Given that there are two P -bond in a molecule of testosterone, how many rings are present in each molecule? 5) A) 2 B) 5 C) 4 D) 6 E) 3 6) How many elements of unsaturation are implied by the molecular formula C5H5NO2? 6) A) 0 B) 1 C) 2 D) 3 E) 4 ESSAY. Write your answer in the space provided or on a separate sheet of paper. 7) Provide the proper IUPAC name for the alkene shown below. CH2??CHCH2CH2CH2CH3 SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 8) Name the compound shown below. 8) 1 MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 9) For which of the following alkenes will cis- and trans- isomers not exist? 9) A) a) only B) b) only C) both a) and c) D) d) only E) both c) and d) ESSAY. Write your answer in the space provided or on a separate sheet of paper. 10) Provide the proper IUPAC name for the alkene shown below. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 11) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? 11) A) E B) Z C) neither E nor Z 12) Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? 12) A) Z B) E C) neither E nor Z 2 ESSAY. Write your answer in the space provided or on a separate sheet of paper. 13) Provide the proper IUPAC name for the alkene shown below. SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 14) Circle the alkene below which has the smallest heat of hydrogenation. 14) ESSAY. Write your answer in the space provided or on a separate sheet of paper. 15) Draw and name all alkenes which have the molecular formula C4H8. SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 16) Circle the most stable alkene in the set of isomers below. 16) ESSAY. Write your answer in the space provided or on a separate sheet of paper. 17) Draw all likely alkene products in the following reaction and circle the product you expect to predominate. 3 MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 18) Which of the following cycloalkenes would be expected to be stable? 18) A) 1 & 3 B) 2 C) 2 & 3 D) 1 & 2 E) None are stable. 19) Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give pent-2-ene as the only alkene product? 19) A) 3-chloropentane B) 1-chloro-2-methylbutane C) 2-chloropentane D) 1-chloropentane E) 1-chloro-3-methylbutane 20) Which of the following alkenes is the major product when 2-bromo-2-methylpentane is treated with sodium ethoxide in ethanol? 20) A) 2-methylpent-2-ene B) 4-methylpent-1-ene C) 2-methylpent-1-ene D) (E)-4-methylpent-2-ene E) (Z)-4-methylpent-2-ene SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 21) Provide the structure of the major organic product of the reaction below. 21) 4 22) Provide the structure of the major organic product of the reaction below. 22) ESSAY. Write your answer in the space provided or on a separate sheet of paper. 23) Draw all likely alkene products in the following reaction and circle the product you expect to predominate. 24) Draw all likely alkene products in the following reaction and circle the product you expect to predominate. 25) Which base, ammonia (NH3) or triethylamine [(CH3CH2)3N], would be a better choice for use in converting 1-chlorohexane to hex-1-ene? Explain briefly. SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 26) Provide the name of the major alkene product that results when (2S,3S)-2-bromo-3-methylpentane is treated with sodium methoxide in methanol. 26) 27) Describe the major elimination products of the following reaction, including any stereochemistry, and indicate which structure will predominate. Explain and defend your answer. 27) 5 28) Provide the major organic product in the reaction shown below. 28) 29) Provide the major organic product in the reaction shown below. 29) ESSAY. Write your answer in the space provided or on a separate sheet of paper. 30) Draw reaction mechanism for the following reaction. Show formation of all likely products and indicate the product you expect to predominate. CH3CH(OH)CH2CH2CH3 H2SO4 6