Chem 212 Survey of Organic and Biochemistry Spring 2006 _____________________________ Print your full name legibly in the space above. Exam 1: Ch. 1-5 23 February 2006 Instructions: 1. If you leave the room for any reason you may not return to continue the exam. 2. No books or notes of any kind are permitted. You may borrow a model kit. 3. Put all your answers on this exam paper. If you want something graded which is written on scratch paper, you must indicate so in the regular space for the answer. Good Luck! 1. Draw a reasonable Lewis structure for each of the following, showing all lone pairs and formal charges where relevant: a. CH3BH2 b. HCN c. HNO3 nitric acid (hint: 3 O’s attached to N, H attached to one O) 2. State whether the structures in each pair below are the same molecule, cis-trans isomers, constitutional isomers, or not related. H3C CH3 H3C H3C CH3 CH3 (CH 3)3CCH 2CH 2CH 2C(CH 3)2CH 2CH 2CH 3 CH3 CH3 CH3 CH3 H3C CH3 H3C CH3 CH3 H3C CH3 CH3 Br Br CH3 Page 1 Chem 212 Survey of Organic and Biochemistry Spring 2006 3. Answer the following questions about the structure below, which is RU-486, also known as Mifeprex or “the abortion pill”. CH3 H3C N a CH3 b 2 CH3 4 d 3 e O c OH 1 f a. How many carbon atoms are in the structure? ___________ b. What is the degree of hydrogen deficiency (unsaturation) of the structure? __________ c. How many hydrogen atoms are in the structure? __________ d. On the structure above, indicate with an arrow one bond that can freely rotate around 360°. Do not point to an atom!!!!!! e. Circle and name three functional groups in the structure above. f. Use the VSEPR method to predict the geometry around each of the following atoms (linear, triangular planar, triangular planar/bent, tetrahedral, tetrahedral/triangular pyramidal, tetrahedral/bent, triangular bipyramidal, octahedral, octahedral/square planar) a ____________ d ____________ b ____________ e ____________ c ____________ f ____________ g. Give approximations for the angles around each of the numbered atoms in Mifeprex: 1 3 2 4 4. Draw a Newman projection for a staggered and eclipsed conformation of 2-phenyl-3chloropentane looking down the C2-C3 bond: Page 2 Chem 212 Survey of Organic and Biochemistry 5. Give the chemical name for the following molecules: CH3 CH3 H3C H3C CH CH3 3 HO OH H3C CH3 O H3C OH H3C NH2 Br H3C OH CH3 HS CH3 H3C H3C Page 3 Spring 2006 Chem 212 Survey of Organic and Biochemistry 6. Next to each name, draw the correct line-bond structure: 2-isopropyl-5-methyl-cyclohexanol trans-1,4-cyclohexanediol 1-chloro-2-propanol m-bromostyrene 3-methylcyclohexene 3-cis-5-cis-2,4-dimethyl-3,5-decadiene Page 4 Spring 2006 Chem 212 Survey of Organic and Biochemistry Spring 2006 7. For each example, draw three different line angle structures: a. C5H10, with an alkene (may have other functional groups as well) Draw three different structures! b. C8H12O2, with an acid (may have other functional groups as well) Draw three different structures! c. C6H14O with a tertiary alcohol (may have other functional groups as well) Draw three different structures! Page 5 Chem 212 Survey of Organic and Biochemistry Spring 2006 8. Draw the structure of the starting materials and the organic products for each of the following reactions. If more than one product can forms, draw only one structure for each. a. 1-Methylcyclopentene treated with hydrogen and a metal catalyst b. cyclopentane treated with bromine and light c. 1,4-Dichlorobenzene treated with sulfuric acid (H2SO4) and nitric acid (HNO3) d. o-chlorophenol treated with sodium hydroxide e. 1-Pentanol treated with K2Cr2O7 f. trans-2-hexene treated with bromine g. 1-pentene treated with water and sulfuric acid h. 2-methyl-2-butanol treated with sulfuric acid and heat Page 6 Chem 212 Survey of Organic and Biochemistry Spring 2006 9. Show how each of the following multi-step transformations can be accomplished. Be sure to draw the structure of the intermediates and all reagents in each case. O H3C OH CH3 H3C O OH CH3 CH3 10. Draw two molecules of ethanol that have a hydrogen bond between them. Use a dashed line for the hydrogen bond 11. Draw the structure of a compound with the formula C5H10O2 that reacts with bromine and is soluble in water. Page 7