{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

SCAN0006 - \‘ H THa C 50 H2804 H2:C 0“ c=cH...

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

View Full Document Right Arrow Icon
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: //\‘ H THa C\ / 50% H2804 H2 /:C/ 0“ c=cH ————> ch—c—c —CH3 \ 50% H20 l 90% d9 o a in \.\ 50AH2804 CH2 ———-—-—-—-——> CH \/ 50% H20 3 OH 80% Mechanism involves a carbocation intermediate; it is the reverse of acid-catalyzed dehydration of alcohols to alkenes Wright 3 The Mmmw—Hm Gmm, inc. Wmms‘er; £00m bf weaken-1m 6| diwayi The overall reaction: (cagzcgcag + ago 3m: {CH3)3COH y/\\ $154531)!!thme Water tarhfiutyi alcohol The meshanifin; stable carbonation: H C H ch H X 7% i \ + CmHEOZ: ~———> /C=n-CH3 + zoi: 1136/ H 53c H ZsMeghyjpmpene Hydwninm ion few-Howl cation Step 2: Water acts as a, nucleophiie to sapmrc ten-bum cation: CH H3C\ m/ ‘10“ ‘ 3+ /H swam + 0:5} Hicm‘FSOK H36 H CH3 :1 (eI‘IeEutyl cation Water tert—Bntylsmrtium ion Step 3: Deprotonation of ter=t=butyloxenium ion. Water acts as a Brfinsted base: CH3 H at, l .. / £1“ H3C=$EQH + Ian-43K CH3 H IgneBmyloxanSum inn Water rentrfimy! ajmhoi Hydmnium ion ...
View Full Document

{[ snackBarMessage ]}