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Final_D - A Nomenclature 91 points Please provide an...

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Unformatted text preview: - A Nomenclature { 91 points) Please provide an acceptable IUPAG name forthe following compounds. CHSCH2\ ’H -‘ 1. xC=G‘%{ . H 'CHQEOCHa 0 CI 5 a. O 9 ’ ('3; CH . Hal, 3 r H H H 8' 9/ 3 ‘ O H E. 2. Reactions (7 points each, total: 35 points) - Please give the major pmduct, or necessary reagents, er surfing materiai for each 01 the following reactions in the box provided. Be sure your drawing indicates the relative orieniaflon of the substituents (5e, stereochemisiry) in the molecule. CH3 ' CchHQBr 1. {CHgCi-{fizfiwfi 2. H3O® 3. exfiéss: 'LjJMH4 4.‘§[email protected] _ 0 fl . 4‘ {CHacHQQCHGOH 5, CHSCHZCH‘QCHZOH 1. 80012 2. (CHfléGUU - 1:529EW‘ I CHacOEH WW 2. SH; ' THF 3. H3 (Note: THF - tetrahydreiufai‘: ' T7 c. MECHANisM': (13 points) _ Provide a detaiied step-by—aep mechanism for the transformation below. Draw an intermediates and Show movement of an electrons with "curved arrows". {#3 Spectroscopy (30 points) Molecule A whose formula is quHmN has the following IR, TH NMR and 134:) NMH spectra (see next page "A"). In the 1H NMR spectrum the numbers above (near) the signals refer to the relative proton integration ratios- Please give ihe structure of g in t: a box provided. ugh :52: x 2.0 r'rr‘r F’Pfl I 5.0 mj—l'Y—T—SY 'TE’" Prater: HEP: "LC 5 m1 0 ED PPH 40 50 BO . T r I IfiTr-rI—rrrr—fi—ITTHW—m—J‘rrfi‘mfiTV‘T—W £03 E. Synthésis : (18 points) Starting [email protected]; any one or two carbon alcohol, and any inorganic reagents. synthesize the foliowing compound: U F. Professof‘s Pot Luck :(10 points) The following seb’lTo‘ffi'éomains three questions, each wozth 10 points. The questions may or may not contain multiple parts. Answer one question only! Omit the other two. Only one'queszion will be graded. if you attempt more than one, be sure to mark out the question you do not want graded. Otherwise. the first question answered will be graded and the second question will be ignored. F1. A. Give [email protected] for each of the following reactions (3 pts. each): 1) I \ . Bré.’ acetio acid . __»-——-———-3.— ' / H2?“ I I N NHQ CF3 H30 \ (CHQscLi {THF 2) __~__._+ N/ 5" Nl-i2 _ __..w___w._.._,.. O B. 01‘ the three staffing mate ‘ale"above. which is the most reactive in electroghiiic aroma: eu stitution reactions? Place yOULanSWEE' in the box provided. (‘l pt.) " _ If f i141. Specie} Question (10 points) - Unlike mammaiian coils, bacteria can uiiiize Ill-amino acids. Since natural amino acids have the L—oonfiguraiion bacteria mus! convert the L-amino acids to their enantiomers. This process is accomplished with the aid of a biological cofaotor (caiaiysi) called pyridoxyl 5'-phosphate (PL?) and is add catalyzed. An abbreviated structure of PLP is given as 1 below‘ Fiease draw a detaiied, step-by»etep mechanism forthe interconversion of one enamiomer of ejanine to another using 1 in water. HR 9&0 H\. 40 C C / + 020 CH3 H ® / + H30 \ Y \ Y N NH2 N NH2 .1. 1 ...
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