Final Exam For Organic II 200pts(Weighted As 300)

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Final Exam for Organic II200pts(Weighted as 300)NameGood luck all round!1) Identify the class of compounds each of the following molecules belongto (15pts).R O HOR C HOR CNR O ROR C NR2OR C O-RHNC OOOR C O C ROR C O-H2) For each of the amides and amines state whether they are primary,secondary or tertiary (4pts).3) Circle one of the above compounds that is reactive enough to react withneutral water (2pts).4) Give two characteristic physical or chemical properties of aromaticcompounds (4pts).Final Exam for Organic IIPage 1

5) Indicate which of the following molecules are aromatic, non-aromatic oranti-aromatic. (Assume all the molecules are planar). (15pts)OH3CH3CCH3CH3H3CCH3H HN ONO2SNNN NO26) Pick one of the above antiaromatic molecules, and use the polygon ruleto demonstrate its antiaromaticity. (8pts)Final Exam for Organic IIPage 2

7) Give the products in six of the following reactions, paying attention toregio/stereochemistry where applicable. (18pts)heatNCCNO CH2CH2CH3PhC CH2Br2, H2OExcess HBrKOHABPhExcess HIOHOFCO, HClCuCl, AlCl3CNOheatCH3Br2, FeBr3NHCOCH3Final Exam for Organic IIPage 3

8) The below heterocycle contains two Nitrogen atoms, and is 6π Hückelaromatic.CH3NNThe lone pairs on the two Nitrogens play different roles in the aromaticity ofthe molecule, and consequently one Nitrogen will get protonated before theother.Describe which one gets protonated first, and explain their differing basicity.(10pts)Final Exam for Organic IIPage 4

9) Give reagents and conditions to accomplish five of the followingtransformations. (15pts)CH3CH3OCH2-OHCH2-O-CH2O2NO2NNO2HO HOH3CH3CHPh PhPh H2CH3(no marks for A)!!!Final Exam for Organic IIPage 5

10) The addition of (1 equivalent of) HBr to cis-1,2-dimethyl-3,5cyclohexadiene generates a mixture of products.H3CH3CHBrmixtureDraw the products, predict their approximate ratio, and mechanisticallyaccount for the mixture of products. (10pts)Final Exam for Organic IIPage 6

11) Circle the stronger base in the following pairs, and in a sentence explainyour choice. (6pts)(a)O2NNH2NH2O(b)F3C NHCCH3H3C NHH2CCF312) Circle the stronger acid in the following pairs, and in a sentence explainyour answer. (12pts)(a)OH3C C OHCO2HCF3CH2 OHCO2H(b)CNO(c)OCl3C C OHBr3C C OHOO(d)H C OHH3C C OHFinal Exam for Organic IIPage 7

13) Name five of the following compounds in IUPAC acceptable terms.(15pts)OOOOOOClONHO14)ORank methanal (formaldehyde), propanone and propanal inincreasing reactivity with nucleophiles, and explain their differingreactivities. (12pts)Final Exam for Organic IIPage 8

15) Fill in the blanks for five of the following reactions. (25pts)Br1) excess Mg?(a)Br2) excess CO2 3) H3ONH21) NaNO2, HCl?(b)2) H3PO2, 5?(d)CH2CH2CNOC Ph?(e)CH2CH2Ph?OC Cl(f)?SOCl2OC?Final Exam for Organic IIHPage 9

16) Give the mechanism for one of the below conversions (10pts)1) BuLiSHSHO2) CH3CH2Br3) H3O , HgCl2CH3CH2CCH2CH3orCH3CH2CH2CH2Cl, AlCl3Final Exam for Organic IIPage 10

17) Give the starting material and mechanism for one of the followingschemes. (19pts)(a)Cl2, KOHNH2H2OO(b)ONa, NH3HC2H5OHH(c)1) CH3Br, Ph3P2) BuLi3) WarmPhC CH2PhFinal Exam for Organic IIPage 11

*Bonus question* (1pt for within 5k, 2 pts within 1k)What is the base rate 10 month salary (i.e. excluding summer compensationand consultancy, etc) for an assistant chemistry professor at Rutgers?Final Exam for Organic IIPage 12

Final Exam for Organic II 200pts(Weighted as 300) Name Good luck all round! 1) Identify the class of compounds each of the following molecules belong to (15pts). ROH ROR O R C O H R C O O-H R C O O C O C R O O-R RCN R C O NR 2 C H N O 2) For each of the amides and amines state whether they are primary, secondary or tertiary (4pts).

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