Solutions_Manual_for_Organic_Chemistry_6th_Ed 278

Solutions_Manual_for_Organic_Chemistry_6th_Ed 278 - CHAPTER...

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Unformatted text preview: CHAPTER 13-NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY A b en zener ing canb e w tten with th ee alte ating dou leb on s o with a ci cle in ther ing. A l l of the ri r rn b dr r cab ons and h r ogens in an un su stitutedb en r yd b zener ing a e equivalent,r ega dless of which s m oli m is r r yb s used. equ va e to i l nt The Japanese web site listed at the bottom of p. 270 also gives proton and carbon NMR spectra. Reminder: The word "spectrum" is singular; the word "spectra" is plural. o 13 1 (a ) 650 Hz 6 300 x 1 0 Hz = 2. 17 x 1 0 6 = = 2. 17 ppm dow nfield r om TMS f = (b) D iffe ence in magnetic field r ( c T he chemical shift does not change w ith field st ength «52 . 17 atb oth 60 MHz a nd 300 MHz. ) r : 6z ( O ( d 2. 17 ppm x ( 60 MHz) = 2 . 17 x l -6 ) x ( 60 x 1 0 H ) = 130Hz )( ) Your predictions should be in the given range, or within 0.5 ppm o/the given value. 7 0,459 gauss x (2 . 17 x 1 0-6) 0 . 1 5 3 gauss 1 3- N um e s are chem cal sh ft values, in ppm, derived f om Tabl 1 3 -3 and the A ppendix in the text. 2 br i i r e CH3 ' c CH3 \ / b C= C b \ / CH3 H C.... a CH3 \ (a ) b .... .... CH3 � b b (b ) a b = = (c ) cp � (e ) H c � --uH H = = * a c H H � � .... C� «5 5-6 «5 0.9 CH3 b CH3 b b (d ) OC J � a b = = /) 7 2 . /) 3 .6 CH3-C-C::C-H c a c CH2-C-O-H b � ( f) a CH3 -C-CH Br 2 b * H a I � CH3 CH3 b h- a b = = «57 2 . «52 .3 H b a � H3 c a b em a b c = = = «5 2- 5 /)2 . 5 /) 1-2 �H3 I b a b = = «5 3- 4 «5 1- 2 Br a H c a b c "" c /) 10- 12 «5 3 ( between tw o deshielding g oups r ) /) 7 2 ( Th eh y ogens l a e ed "c" a e not equiva ent. . dr bl r l Th ey appea atr oughl the sa e che cal shift r y m mi b ecause the su stituent is neithe st ngly elect onb r ro r d onating no withd awing. r r ) 271 H ...
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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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