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UT Knoxville CHEM 360 - exam 2 answer key sprin 2013

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Chern 360 Exam 2 Spring 2013 NAMEY.QHj ~f"!\:!<V\OIC'Prof Bartmess (Carey8) ~- This is a 55 min exam. Please think your a swersl. (14) through before committing them to paper.- Be legible; if I can't read it, it's wrong.2. (12) - Don't put any answers on the back of the pages(although you can use the backs for scratch paper);3. (34) material on the back of pages will not be graded.- BE SURE THAT YOU HAVB FOUR DIFFERENT PAGES4. (16)5. (24)l.(14) Give the correct substitutive nomenclature for the following structures. You can ignoreRlS stereochemisotry~(£J(YOCH3CIHo2.(12) For each of the following horizontal groups of3 acids, indicate which is the strongest acidon each line by writing "strongest" under it, and which is the weakest by writing "weakest"under it.N&+~t-\-tl{€A. ~~~ +S3#Fillin the missing reagent/reactant/product(s). Showallorganic products.Pay attention toregiochemistry and stereochemistry. One arrow may mean morethanone set of reagents; be sureto make clear which reagents are in discrete steps.-t ~a. ~EtH~/o\ HBr _f-k,_ ~.r- - ~.-Z-LtJ.-o"j·r~;()(i3Vh.o6@)clt~-:\jS~OH+?...~oC'I'D3>\' Pcc.I( ~+I?~~•••H-CQ~\pJ?C)rd.~-t-\0°-------_.H2NOH/" t01JH•••~ -r-~e.0t-~.h::rL'~ .,'IV'~M:0Et2NH0-tL{CJU'-~•••.:r1-(ilnPrBr~~-+LCH3CH2CH2CH2OH~0c\.{"L:-U*"'L..~) ~-{30++~g.~~PhMgBrH2O-+~~CN~~Et20 H2SO4Dh.-j-1...-t1....-aaM1~a~CI~NH2••4.(16) Present a high-yield synthesis of one of the following molecules, starting from whateverof the following are needed: non-cyclic mono-functional alcohols of four or fewer carbons,benzene, and any necessary inorganic reagents, including cyanide and CO2. You need not givethe mechanism for each step, but all necessary reagents and solvents must be shown, and eachchemical step (different reagents) must be clearly indicated as a separate step.Me OH~y~~~®O~@y6H~Ok.---\-~~:---~-C--:--C- )S5u..~~\.J+\'L'fV\CJJ'f--5. (24) a. Give a complete curved-arrow mechanism for formation of this ester from thehydroxyl-acid shown. Show all intermediate structures and any important resonance forms of~m~~~r~0=0°+l2 5-t(J!(.U\,~OHH2S04HOII •o .}-\ heat~H~HCO'-H)D<) \Lri~7f2}/()~r<1J-tl ~\~~~\~OHl--YJ ~.-t1S0~-\:~ c. Circle the straight arrow corresponding to the rate-determining step.--('\Jl-This is inherently an unfavorable equilibrium for forming the product «50%). However, thereare ways to get a reasonable amount of product from this specific reaction. State one viable


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UT Knoxville CHEM 360 - exam 2 answer key sprin 2013

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