First Exam Name PRINT Chemistry 3332 Signature February 17 2006 ID Last First Please circle class time Dr Bean s 10 00 AM Dr Bean s 1 00 PM Page Score 1 12 pts 2 20 pts 3 18 pts 4 18 pts 5 11 pts 6 11 pts 7 10 pts TOTAL Note Present your student ID when you return the exam booklet A Nomenclature 12 points 4 points each Give an acceptable name for each of the following compounds Be sure to note stereochemistry where appropriate 1 H O 2 H 3 H O OH B Facts Total Points 20 1 Place the following carbocations in order of increasing stability 1 least stable 3 most stable 3 pts OH OH OH 2 Place the following compounds in order of increasing reactivity in an SN2 process 1 least reactive 3 most reactive 3 pts Br Br Br 3 Place the following molecules in order of increasing reactivity in a Diels Alder reaction 1 least reactive 3 most reactive 3 pts O CH3O C CH3O O CH3 C O 4 Place the following compounds in order of increasing reactivity with HI 1 least reactive 3 most reactive 3 pts O O CH3CH2 O CH2CH3 5 Answer the following questions about the compound below Place the answers in the appropriately labeled boxes a How many distinct types of protons does the compound have b What is the theoretically predicted multiplicity splitting pattern of the signal for the proton labeled a c How many distinct types of carbons does the compound have d What is the multiplicity of the signal in the proton coupled 13C NMR spectrum for the carbon labeled b 8 pts a number of proton types O CH2 C CH3 CH3CH2 b CH a b Ha multiplicity c number of carbon types CH2CH3 d Cb multiplicity C Reactions Total 36 points 6 points each Please provide the major product unless otherwise indicated in the answer box Be sure your drawing indicates stereochemistry if applicable Partial credit is awarded only when intermediate products are shown below the reaction 1 Br2 H 2O 1 2 NaOH 3 MgBr 4 H3 O 2 1 O3 2 CH 3 2 S 3 NaBH4 EtOH 4 H 2SO4 heat 3 O 1 HBr excess 2 CH 3 3CO K CH3 4 NBS 80 C Major Product 5 OCH3 CH3 Heat CH3 O 6 1 CH 3 C O CH3 C H 2 C H 3 PCC CH2 Cl2 4 heat Na Minor Product D Mechanisms 11 points Please provide a clear mechanism for the reaction below Use curved arrow notation to indicate electron flow Show all intermediates and all formal charges O H3CO O 1 Br2 CCl4 2 CH 3O Na CH 3OH Br E Synthesis 11 points Synthesize the molecule below using any of the following reagents cyclohexane and alkanes alkenes alkynes or alcohols of two carbons or less any oxidizing or reducing agents and any peroxyacids OCH2CH3 CH3 O F Spectroscopy 10 points A compound with the formula C9H8O exhibits the IR 1H NMR and proton decoupled 13C NMR spectra shown below Please identify this compound and draw the structure in the box provided below