Solutions_Manual_for_Organic_Chemistry_6th_Ed 263

Solutions_Manual_for_Organic_Chemistry_6th_Ed 263 - 11-61...

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Unformatted text preview: 11-61 Lethe'saxialnalbyohol isidoxidnigzedhetefnacttism. es as fast the equatorial alcohol. (In the olden days, this Tobserbegiioncwasconsederias evitdence suggesting the stereochemistry of a ring alcohol.) vat us as A EQU TORI L A A HO Second,ofitHisand chrothmattehteooxiordmattihoen Coccur. sLinett'ws loookts epsat:each) fomechaninsofm.the chromate ester; and known at f =O 1 rmatio 2) loss ::7'.( H( � Step2.0� FASTER � ; ��� 0\.,Cr03H X I A OH H H about So what we ion an in axi becaus the areal poseitisotan equataolriinadolteposctitiknow.thSo whatht theieseStaseylpsposet mstiweri?oenWee knoweetar -lanyhtimiattigrnsguobssuptetip?tatuentWesaxiwoulmorexpectblhastehattthhee diequatorial chra omatnse ester woulfd form faster tthhan the axial chromate ester; sindce this is contrary to axi r o whatar tethliemdatti inag,shwe woulepd expect tlhikeelapprtoobe raofte-tlhime basiti neg.(pHow about Stere)pt2?the equateloimriainl ation ihydrogen (axial ow,oStmate estisenot)r wouldybe fachster than the apprroobablyofwate basoe to thteheaxial s chr hydrrets icogen (equatnoassociaotematwietestsuch)re . aMorrgaeovero, e axiasl iestconsiissmorntthewimotht itvhate erdelatotivleeavear tedueofto rial chr d h la e gr Thi s each te congesmtiexperiment. Thus, it is reasonable to conclude thrat the second step of the s rmechanin sfrmo is roate-limiting. eactio 11-)a(<0H1 ° �'Clp 0 (y'H C-p/,O Oo 62 I Cl H Cl O :CI:- H O-P=O Cl1 oo O O <00-P= QVO Cl o0 o Cl - 'Cl O CI (Cl Ell H H Cl o Cl (';( H �H :o-f=o o-p= CI LiZ \.fin H � > CI continued on next page 1 1 If in � H 1 ,3- 0 __ 00 � 00 \/ I 0 0 � + I") 00 � 1 00 00 " 00 00 � 00 00 1 1 __ + H H 256 �:N ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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