{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Solutions_Manual_for_Organic_Chemistry_6th_Ed 112

Solutions_Manual_for_Organic_Chemistry_6th_Ed 112 - lEaviNg...

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

View Full Document Right Arrow Icon
6-22 slow planar carbocation .. - :Br: + + CH3CH20H2 Be (or simply HBr) 6-23 The structure that can form the more stable carbocation will undergo S N 1 faster. (a) 2-bromopropane: will form a 2° carbocation (b) 2-bromo-2-methylbutane: will form a 3° carbocation (c) allyl bromide is faster than n-propyl bromide: allyl bromide can form a resonance-stabilized intermediate. (d) 2-bromopropane: will form a 2° carbocation (e) 2-iodo-2-methylbutane is faster than t-butyl chloride (iodide is a better leaving group than chloride) (f) 2-bromo-2-methylbutane (3°) is faster than ethyl iodide (1°); although iodide is a somewhat better
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: lEaviNg group, thE diFfErEncE bEtwEEn 3° and 1  carbocatioN stabiLity doMiNatEs 6Ã24 ÄoniZatioN is thE ratE±dEtE·iniNg stEp ¾n S ² l. Anyt¶ing that stabilizEs thE intE·EdiatE wiÅl spEEd thE rEactioƽ Both oF thEsE compounds ForÇ rEsoNaÆcE±stabilizEd intERMEdiatEsÈ H ( H I ±² H H H V H allylic bEnzylic + ( ) CH2 -² O CHz ³ < } H± 6±25 H H I t± + I ± CH³ ´ T ´ t HCH³ • BrÉ + CH³ µ C ¶ CHCH³ + H µ R-CH±CH³ ( B r C H H cH3 ¶ ± CHCH3 ·¸ ¹ f--² ·h3 ² Chch3 / I I .. ±²³´ (i. i :?: C ¸ 3 CH³CH±´ 9 : H ¹ + ? CH3 CH±CH3 H Ch±CH³ 105...
View Full Document

{[ snackBarMessage ]}