Solutions_Manual_for_Organic_Chemistry_6th_Ed 263

Solutions_Manual_for_Organic_Chemistry_6th_Ed 263 - 11-61...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

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,up.ht 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 ...
View Full Document

This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

Ask a homework question - tutors are online