front cover.doctest_01.docFirst Exam Name (PRINT) . Last, First Chemistry 3332 Signature February 16, 2007 ID# Please circle class time. TOTAL Note: Present your student ID when you return the exam booklet Page # . Score 1. 12 pts. 2. 18 pts. 3. 18 pts. 4. 12 pts. 5. 14 pts. 6. 14 pts. 7. 12 pts. Dr. Bean’s 10:00 AM Dr. Bean’s 1:00 PMA. Nomenclature: (12 points) Give an acceptable name for each of the following compounds. Be sure to indicate the stereochemistry where appropriate. 1 BrOCH3 2 OOHCH2CH3 3 OOB. Facts: Total Points = 18 1. Place the following alkenes in order of increasing stability. (1=least stable, 3=most stable) (3 pts.) 2. Place the following carbocations in order of increasing stability. (1=least stable, 3=most stable) (3 pts.) OCH3CH2CHCH2CH3 OCH2CH2CHCH3CH3 OCH3CH2CCH3CH3 3. Place the following molecules in order of increasing reactivity in a Diels-Alder reaction. (1=least reactive, 3=most) (3 pts.) OCH3HOCH3H HOCH3HCH3O HOCH3OCH3H 4. Put the letter of the reaction with the faster rate in the box. (4 pts.) Cl CNNaCNCl CNNaCNab 5. Answer the following questions for the molecule below and place the answers in the appropriate boxes. (i)How many distinct types of protons are present in the molecule? (ii) How many distinct carbons are present? (iii) & (iv) What are the theoretically predicted multiplicities (splitting patterns) of the signal for protons b and c? (v) What is the multiplicity of carbon a in the proton-coupled 13C NMR? (5 pts.) (i) # of proton types (ii) # of carbon types (iii) multiplicity of Hb (iv) multiplicity of Hc abcOHH3CHCH3CHCH2CH2CH3 (v) multiplicity of CaC. Reactions: Total = 30 points, 6 points each Please provide the major product in the answer box unless indicated otherwise. Indicate stereochemistry with wedges and dashes if applicable. Partial credit is awarded only when intermediate products in a multi-step reaction are shown below the reaction. 1. 2. Na / NH31. KOH / 200°CCH2Br3. Br2/H2O4. NaOHCHCH2CH3Br 2. 2. O33. (CH3)2S1. CH3O-Na+4. NaBH4/EtOH(H3C)3CBrCH3 3. HeatCH3O+OO4. NBS / light / 0°CNote: NBS=N-bromosuccinimideMajor Product Minor Product+ 5. 1. MCPBA2.CH3CH2CH C3. H2SO4/HeatCH3CH3MgBrD. Mechanisms: (14 points) Provide a clear mechanism to explain the formation of the product. Use curved arrows to indicate “electron flow”. Remember to show only one step at a time. Show all intermediates and all formal charges. Do not show transition states! OHBrBr2/H2OE. Synthesis: (14 points) Synthesize the molecule below using any of the following reagents: alcohols, alkanes, alkenes and/or alkynes of three carbons or less, any inorganic reagents, any oxidizing or reducing agents, and any peroxyacids. CH3CH2OF(a). Spectroscopy (12 points) A compound with the formula C10H10O exhibits the IR, 1H NMR and proton decoupled 13C NMR spectra shown below. Please identify this compound d and draw the structure in the box provided