First ExamChemistry 3332February 19, 2010Name:_________________________________Signature:______________________________ID#___________________________________PLEASE CIRCLE CLASS TIME!10:00 AM1:00 PM4:00 PMTotal:_____________NOTE: Present your ID when you return the exam bookletPage # Score1.16 pt2.18 pt3. 18 pt4. 12 pt5. 12 pt6. 12pt7. 12 [email protected]. Nomenclature: (16 Points)Give an acceptable name for each of the following compounds. Be sure to note stereochemistry whereappropriate.OHOClHOHH2C CHCH2OH [email protected]. Facts:18 points1. Place the following halides in order of increasing reactivity in an SN1 process. (1=least reactive, 3=mostreactive) 3 pts2. Place the following halides in order of increasing reactivity in an SN2 process. (1=least reactive, 3=mostreactive) 3 pts4. Place a Y in the box below any halide that will form useful Gringard reagent and an N below any that willnot (4 pts)6. Answer the following questions for the molecule shown below and place the answers in the appropriateboxes. (i) how many distinct proton types are present in the molecule. (ii) How many distinct carbons arepresent? (iii) and (iv) What are the theoretically predicted multiplicities (splitting patterns) of the signals forthe protons labeled a and b ? (v) What is the multiplicity of the signal for carbon c in the proton-coupled13C-NMR (5 pts)(i) number of proton types(ii) number of carbon types(iii) multiplicity of Ha(iv) multiplicity of Hb(v) multiplicity of CcOBrOBrOBrBr BrBr3. Place the following alkenes in order of increasing stability. (1=least stable, 3=most stable) 3 ptsOBr [email protected]. Reactions: Total = 30 points, 6 points eachPlease provide the major product or the reagents in the answer box. Be sure your drawing indicatesstereochemistry if applicable. Partial credit is awarded only when intermediate products in a multi-stepreaction are shown below the reaction.1.2.3.Br1.(CH3)CO-K+2. MCPBA3. HCl1. LiAlH4(2 eq)2. H3O+(xs)3. PCC/CH2Cl2OOCH3Br Br1. NaNH2/ 150°C2. H3O+3. Sia2BH4. H2O2/ [email protected] / light / 0 C4.1. PBr32. NaCN / acetone5.Major Product Minor [email protected]. Mechanism(12 points)Provide a clear mechanism to explain the formation of the product shown in the reaction below. Usecurved arrows to indicate "electron flow". Remember to show only one step at a time. Show allintermediates and all formal charges.OHOCH3OH / H2SO4100 [email protected]. Synthesis (12 points)Synthesize the molecule below using any of the following reagents: alcohols and/or alkanes of twocarbons or less, cyclohexane, any inorganic reagents, any oxidizing or reducing agents, and [email protected]. Spectroscopy:12 pointsAcompound with the formula C8H18O exhibits the IR,HNMR and proton coupled CNMR spectra shown below.Please identify this compound and draw the structure in the box provided below.01234PPM22