Name _______________________Page 1I. (28 points)Complete the f ollowing reactions as directed. Transformations requiring sequential experimental stepsshould be numbered appropriately. Show the major organic product(s) unless otherwise specif ied.Abbreviations f or reagents are not allowed. If a product forms as a stereoisomeric mixture, draw oneand write "+enantiomer" or "+diastereomer" in the box.C C CH3CCCH3HHOHC C H+NaBr + H24only this product continues444CH3CH3CH3COKA.B.C.44HOOHH2Pd/COOOHCH2CH3PhH1) O32) H2O2OCH2CH3PhHCH2Phonly this alkenep roduct!41) NaH2) CH3Br1) Na, NH32) OsO4CH2CH2CH3BrOOHOOCH2CH3PhHOH+1) NaNH22) PhCH2IKEYCHH3CCH3Compound BName _______________________Page 2II. (24 points)Compound B undergoes bimolecular elimination when treated with NaOCH2CH3to f orm a single,major product.i) Draw the curved arrow mechanism for this reaction using the chair conformation that gives thefastest rate of elimination, andii) Draw the elimination product (Product C).8i) curved arrow mechanism for reaction with NaOCH2CH34A.i) Compound D is a stereoisomer of Compound B. The rate of bimolecular elimationof Compound D to f orm Product C (above) is expected t o bethesameas fasterthan slowerthan (circle one)the rate of bimolecular elimation of Compound B to form Product C.NaOCH2CH3CH3CH2OHB.2C.The f ollowing results in more than one product. Write all predicted products of this reaction in thebox provided. No rearrangements were observed.CH3CH2OH4ii) Major elimination product2CH2CH3BrCHH3CCH3Compound DCH2CH3BrProduct CHH3C CH3CH3Briii) Compound B and Compound D are best described as being _______________________________of each other.ii) In one or two sentences, explain why the rate would or would not change asindicated in part i above.4CH2CH3HHHHHCCH3H3CBrHCH3CH2OCHH3CCH3CH2CH3The isopropyl group would be equitorial on the ring in Compound D for theconformation that allows E2. Since that is a more stable conf ormation than theconformation shown f or Compound B, the molecule would spend more time in thatconformation and E2 would occur more rapidly.diastereomersHH3C CH3CH3OCH2CH3OCH2CH3H3C CH3CH3H+KEYName _______________________Page 3III. (34 points)Metolachlor is a potent herbacide used to control a variety of weeds. An almost 10-year-old study(Tetrahedron, 1997, 53, 10513) has shown that, under certain conditions, this compound undergoes anintramolecular SN2 reaction that produces a compound with a very good positive-oxygen leaving group(Compound J). One of the things observed in some intramolecular SN2 reactions is that typically pooroxygen nucleophiles, such as ethers, can participate in these reactions. Surprisingly, Compound J canparticipate in a second SN2 reaction with water.Compound JNClOOmetolachlorN OOarrows f or intramolecular SN2Structure of Compound J andarrows f or intermolecular SN2Complete the reaction, including curved arrow mechanisms f or each step and the structures ofCompounds J and K.HO Hother or ganic p r oduct+Compound KA.B.HCl3,3-dimethyl-1-butene2-chloro-2,3-dimethylbutane+i) Fill in the following boxes with the structures or names indicated.ii) In the space below, provide the complete, step-wise, curved arrow mechanism for the transformation of3,3-dimethylbutene to 2-chloro-2,3-dimethylbutane.CH3CH3CH3CCHCH3Cl+ enantiomerName the above molecule2644648N OOCH3CH3OHCH3CH3CH3CCHCHH(S)-2-chloro-3,3-dimethylbutaneClCH3CH3CCHCH3CH3ClCH3CH3CCHCH3CH3CH3CH3CH3CCHCHHHClCH3CH3CH3CCHCHHHClCH3CH3CCHCH3CH3KEYH2OWhen Compound A is treated with water in the presence of an acid catalyst, two unchargedstereoisomeric products result. Draw these products, showing appropriate stereochemistry.Compound Ai)H2SO4(cat)33The f ollowing reactions yield products that are stereoisomeric mixtures (ignore all byproducts) -complete these reactions, showing stereochemistry clearly f or one product. Also, answer the questionsabout the stereoisomers that form.drawthereactiveintermediatethatleadsto theprod uct you d raw in the next boxName _______________________Page 4IV. (28 points)1. BH32. H2O2/NaOHDescribe the products:( check all that apply)a diastereomeric paira mixture of >2 stereoisomersall are chiral moleculesa racemic mixture+Draw one of the stereoisomeric products66A.B.i)ii)iii)44at least one is achiralDescribe the products:(check all that apply)a diastereomeric paira mixture of >2 stereoisomersall are chiral moleculesa racemic mixtureat least one is achiralCH3ii) The two products of the above reaction are best described as being ___________________________of each other.CH3H3CCH3OBrHIOCH32CH3H3COHOHH3CCH3diastereomersH3C HH3CH2C OCH3HO HxxH3C CH2CH3H3CH2C CH3I HxxCH3BrCH3BrHH3COKEYName _______________________Page 5V. (26 points)When the Compound D was dissolved in ethanol many products resulted, however no evidence ofrearrangement was found. Using the information given, predict these product(s), drawing them in theappropriate spaces.all products having molecular f ormula C9H18O2all products with a molecular f ormula of C7H12OCompound D366+A.B.CH3CH2OHOBrCH2CH3Provide the missing inf ormation in the multi-step syntheses below. Include stereochemistry whereneeded. Also remember to number steps if more than one discrete transformation is represented by asingle arrow.CH3CCH2CH3HHOH3CH2CCNCH3Hsingle stereoisomerii)1. B2H62. H2O23.3H3CSOOClNNHi)single stereoisomerH3CSOOO+H3CCH3242O SOOCH3(CH3)2NHNaCNCH3CCH2CH3BrHH3CSOOClN1.2.