Question

For each of the following pairs of organic molecules, circle the one that would react with a given nucleophile at a faster rate in the Sw1 reaction, and briefly explain your choice. нссн, vs. H₂C CH₂ CH Hoc tots vs. Ho C^ots 6. Each of the following carbocations can undergo a rearrangement to give a more stable carbocation. In each case, draw the structure of the rearranged carbocation, and show the mechanism of the 1,2 hydride shift or 1,2-alkyl shift leading to its formation. H3 CH3 CH3 X OH c. Hint: Think about ring strain. H ct's CH3

Answer 1

(a) H30 - Hzc a cha and (Hgc сна ing group than that Because cle) is a betrea leaving group than OF F(-) and as a gesult Crenegation of Carbocation forms easily and for this season 3N1 geachow will occur at faster rate. от - This compound will reach -CH₂ pašter sate for SNI seaction ең НА С ОТ, and Hoc- От 3 In this case we can see that both the compound have same leaving group lie. Oosts Otor сүз - Ors'-) не сиз ОТ 3 уп взе 3, аЫle 20. co5 SocAKohy Forms - от 3 (-) +3 Не — ен, на с оту — Те 43 3} able .. C43 bo. сH3 Codon Fo33 That's why . H₂C O TS This compound will seach Fo3 }е. Але fo5 5 1 3 еасhоn.

and In this case also we the compound have le. Bpr) Bess - can bee that both same leaning group - Вт (-) This compound foams more stable Ben2ytic co9 Боса Но Forms - Art-> Phenyl carbocation is very unstable and not Easily forms tha} 3 usky - Br This compound will 2eac} [о}ел за }e Fon Зм еасhоn.

cas #sc. (CH3 CH3 на 1, 2- енз азоор Shirts Нас CHO G CH₂ н.е. Those 3+aЬle 3. Caboca How forms ОН b) H3C сиз 1, 2. hydside shift occurs This casbocation 15 3 Fabilized by 2e3on once with the lone paias op oxy-gen atom. о Hoe

(+) енз Ring Expansion бессо CH₂ formation of CH₃ море 5+able 3°, саз Locahow Oce D33,