Solutions_Manual_for_Organic_Chemistry_6th_Ed 347

Solutions_Manual_for_Organic_Chemistry_6th_Ed 347 - CHAPTER...

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Unformatted text preview: CHAPTER 16-AROMATIC COMPOUNDS Note: The representation of benzene w ith a circle to represent the 1t s ystem is fine for questions of nomenclature, properties, i somers, and reactions. For questions of mechanism or reacti vity, however, the representation with three alternating double bonds (the Kekule picture) is more informative. For c l arity and consi stency , thi s Solutions Manual will use the Kekule form exc lusively. K ekule form used i n the Solutions M anual 16- 1 o • � e quivalent representati ons of henzene c::::> © H H • • • H C. • • • C· • ' -C . • H H. • C· C • • C,, . H .C. ' 'C . C· • • C CH ' ' .. C · H H' • . H H 1 6-2 All values are per mole . (a) benzene 1 ,4-cyclohexadiene MI = H -208 kJ + -240 kJ 32 kJ - 49. 8 kcal - 57.4 kcal + 7 .6 kcal (b) - benzene cyclohexene -208 kJ - 49.8 kcal - 28.6 kcal - 2 1 . 2 kcal - 55 .4 kcal - 28.6 kcal -26 . 8 kcal f.,}{ f.,}{ - 1 20 kJ = - 88 kJ -232 kJ - 1 20 kJ - 1 1 2 kJ (c) - 1 ,3-cyc lohexadiene cyc lohexene = 1 6-3 (a) H .... C,..C.::::-C' H II H I H H 1---I H 'c-:::' 'c' II I H C I ..... C, -:::.C .... H H C I ..... C.::::- ,..C .... H H C { H H "- H / H "H "H "C-C C=C ---- II II I I C-C C=C , , / H H H } 3 41 ...
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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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