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1 Chemistry 1304 Name (please print) Exam 6 (105 points) May 2, 2018 n my honor, I have neither given nor received unauthorized aid on this exam. Signed Date 1. (6 points) A triglyceride has functional groups (name the group) and is made from long chain and a trialcohol called. 2. (8 points) Draw semi-condensed or fully expanded structural formulas for all possible isomers of C 3 5 Br. 3. Consider the molecule on the right. The numbers refer to the individual carbon atoms in the following questions C C C 2 C 4. a. (2 point) Insert any lone electron pairs that are not shown b. (2 points) List the atoms that have sp hybridization c. (2 points) List the atoms that have sp 2 hybridization d. (2 points) What is the C 9 C angle at C-9? e. (2 points) What is the C 10 angle at C-10? 5. (6 points) Polyethylene is encountered daily in many common items such as grocery bags and milk bottles. Another useful polymer with very hydrophobic properties that make it a useful surface coating is Teflon. Draw the structure of polyethylene and Teflon.

2 2 6. (18 points) Write the clear, semicondensed of fully expanded structural for each of the following compounds acetone cyclohexyl acetate 3-methylbutanamide 2-nitropropanal 3-chlorobenzoic acid 3-phenyl-trans-2-pentene 7. Consider the three organic compounds shown below. a. (9 points) Write the systematic name of each compound below its structure. b. (4 points) Circle any carbon atoms that are chiral centers (asymmetric carbons) in these structures. Br C 2 C 3 N C C C C C 3 C 2 C 3

3 3 8. (9 points) Write complete structural formulas of the missing monomers or the missing polymers in the following reactions. In the blank, indicate whether the polymerization process is addition, condensation, or ring-opening. C 2 2 N C C C C 2 C 2 C 2 C + n 9. (4 points) In the structures drawn or that you drew in the problem above, circle the peptide bond. 10. (6 points) Draw the fully expanded structure of 1,4-diethylbenzene and the product of its reaction with nitric acid, N 3

4 4 11. (20 points) Draw complete structural formulas for products of the reaction sequence shown below. You may write either fully or partially condensed formulas as long as the molecular structure, including the positions of functional group, is clearly shown. [Note that it is often helpful to show all atoms, including at the site of the reaction.] [] C 3 C 2 A C 6 10 B C C C excess " 2 " - 2 C 3 N F C 7 13 N D C 6 12 E C acetic acid G C 6 10 C 6 12 I C excess Br [] No Reaction Na J C 6 11 Br and L

5 Chemistry 1304 Name (please print) Exam 6 (105 points) May 2, 2018 n my honor, I have neither given nor received unauthorized aid on this exam. Signed Date 1. (6 points) A triglyceride has functional groups and is made from long chain and a trialcohol called. 2. (8 points) Draw semi-condensed structural formulas for all possible isomers of C 3 5 Br. 3. Consider the molecule on the right. The numbers refer to the individual carbon atoms in the following questions C C C 2 C 4. a. (2 point) Insert any lone electron pairs that are not shown b. (2 points) List the atoms that have sp hybridization c. (2 points) List the atoms that have sp 2 hybridization d. (2 points) What is the C 9 C angle at C-9? e. (2 points) What is the C 10 angle at C-10? 5. (6 points) Polyethylene is encountered daily in many common items such as grocery bags and milk bottles. Another useful polymer with very hydrophobic properties that make it a useful surface coating is Teflon. Draw the structure of polyethylene and Teflon.

6 2 6. (18 points) Write the clear, semicondensed structural formula (e.g., see previous problem) for each of the following compounds acetone cyclohexyl acetate 3-methylbutanamide 2-nitropropanal 3-chlorobenzoic acid 3-phenyl-trans-2-pentene 7. Consider the three organic compounds shown below. a. (9 points) Write the systematic name of each compound below its structure. b. (4 points) Circle any carbon atoms which are chiral centers (asymmetric carbons) in these structures. Br C 2 C 3 N C C C C C 3 C 2 C 3

7 3 8. (9 points) Write complete structural formulas of the missing monomers or the missing polymers in the following reactions. In the blank, indicate whether the polymerization process is addition, condensation, or ring-opening. C 2 2 N C C C C 2 C 2 C 2 C + n 9. (4 points) In the structures drawn or that you drew in the problem above, circle the peptide bond. 10. (6 points) Draw the fully expanded structure of 1,4-diethylbenzene and the product of its reaction with nitric acid, N 3

8 4 11. (20 points) Draw complete structural formulas for products of the reaction sequence shown below. You may write either fully or partially condensed formulas as long as the molecular structure, including the positions of functional group, is clearly shown. [Note that it is often helpful to show all atoms, including at the site of the reaction.] [] C 3 C 2 A C 6 10 B C C C excess " 2 " - 2 C 3 N F C 7 13 N D C 6 12 E C acetic acid G C 6 10 C 6 12 I C excess Br [] No Reaction Na J C 6 11 Br and L

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