Exam 1Chemistry 3332Febuary 19, 2011Name:_________________________________Signature:______________________________ID#___________________________________PLEASE CIRCLE CLASS TIME!10:00 AM1:00 PM4:00 [email protected][email protected]. Facts:18 points1. Place the following carbocations in order of increasing stability (1=least stable, 3=most stable)2. Place the following resonance contributors in order of increasing stability.(1=least stable, 3=most stable)4. Place the following compounds in order of increasing reactivity in a Diels-Alder reaction(1=least reactive,3=most reactive)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 Cb3.Place the following alkenes in order of increasing UV absorbance maxima (1=shortest wavelength, 3=longestwavelength)OOH OH OHNCH3OCH3NCH3OCH3NCH3OCH3O [email protected]. Reactions: Total = 36 points, 4 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-step reactionare shown below the reaction.1. Br2/ H2O2. NaOH3. HClCH31.3.1. (CH3)CO-K+2. BH3-THF3. H2O2/ NaOH4. Na2Cr2O7/H2SO4/H2O1. HgSO4/ H2SO4/ H2O2. CH3-C3. H2/ Pd(BaSO4)/quinoline2.C-Na+, then H3O+HC [email protected]. HBr / 0CMajor product Minor product5.1. Hg(OAc)2/2. NaBH43. HI (XS)[email protected]. Mechanism(10 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.OO1. CH3O-Na+2. [email protected]. Synthesis (10 points)Synthesize the molecule below using any of the following reagents: alcohols, alkanes,alkenes, and oralkynes of three carbons or less, cyclohexane, any inorganic reagents, any oxidizing or reducingagents, and any peroxyacids. (Your synthesis must account for the stereochemistry to get full [email protected] compound with the formula C9H12O exhibits the IR and1HMNR shown below. Please identify thiscompound and draw the structure in the box provided below. (6 pts)012345678PPM020406080100120140160PPM2H