10_spectroscopy_NMR_class

10_spectroscopy_NMR_class - "#$&($"...

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Z#1C#1# induced magnetic field induced pi electron circulation creates a magnetic field which opposes B o H H deshielding therefore less energy needed to resonate - shifted down field. (to the left) B = B o + Bi Bo !"# 7.0 - 7.5 $* F F F F F F F F F F F 211#&.:)8&'0#1(.g.VE?`.""; (:2#,8#8. '+%#&.:)8&'0#1(.`?J.""; 8#(:2#,8#8 F F F F F F F RE`T.-11+,#1# g.VE?].""; (:2#,8#8 FLH FLH HFL HFL HFL g.L?].""; !"# $+ @,>)1#(. . 218+$#8. ;-01#%2$.72#,8. 218+$#8. ;-01#%2$.72#,8. @,8#:)8#(. 218+$#8. .#,#$%&'1(.$2&$+,-%2'1. $&#-%#(.-.;-01#%2$ 72#,8.O:2$:.'""'(#(.Z. ' F. H. H 218+$#8. .#,#$%&'1(.$2&$+,-%2'1.. $&#-%#(.-.;-01#%2$. 72#,8.O:2$:.'""'(#(.Z. ' 3 F H. F. 8#(:2#,8210.%:#&#7'&#.,#((. 1##8#8.%'.&#('1-%#.V.(:27%#8. 8'O1.72#,8?. (:2#,8210.%:#&#7'&#.;'&#.#1#&0). 1##8#8.%'.&#('1-%#.V (:27%#8 +"72#,8?. Z.P.Z. .V.Z. ' 2 .P.L?L.V.L?` Z. . ' Z.P.Z. .S.Z2 ' . P.JVE] Z. . ' @,('.'X)0#1.2(.#,#$%'1#0-%29#.-18.O2%:8&-O(. #,#$%&'1.8#1(2%).7&';.HVF.<'18.48#(:2#,82105. !"# $, @""&'X2;-%#.h&'%'1. H:#;2$-,.!:27% Type of Proton 1 Alkyl, RCH3 2 Alkyl, RCH2R 3 Alkyl, R3CH Allylic, R C C R R CH3 Type of Proton Alkyl bromide RCH2Br Alkyl chloride, RCH2Cl Vinylic, R2C=CH2 Vinylic R C C H R R Chemical Shift ( , ppm) 3.4 3.6 3.6 3.8 4.6 5.0 5.2 5.7 6.0 9.5 9.5 10.5 0.5 6.0 a 1.0 5.0 a 4.5 7.7 a 10 13a :)8&'0#1 <'18210 F N N Chemical Shift ( , ppm) 0.8 1.0 1.2 1.4 1.4 1.7 1.6 1.9 Aromatic, ArH Aldehyde, O RCH Ketone O RCCH3 2.1 2.6 2.2 2.5 2.5 3.0 3.1 3.3 3.3 3.9 3.3 4.0 3.3 4.0 !"# Benzylic, Ar-CH3 Acetylenic RCCH Alkyl iodide, RCH2I Ether, ROCH2R Alcohol, RCH2-OH Ester, RCOOCH2R Alcohol hydroxyl, ROH Amino R-NH2 Phenolic, Ar-OH Carboxylic, acid O RCOH N a D:#.$:#;2$-,.(:27%.'7 %:#(#."&'%'1(.9-&).21. 8277#&#1%.(',9#1%(.-18. O2%:.%#;"#&-%+&#.-18. $'1$#1%&-%2'1? F %N H:#;2$-,,).-18./-01#%2$-,,).\B+29-,#1%.:)8&'0#1[( h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i F i H HFLZ& F!"# 67.-1).F.2(.&#",-$#8.<).i.'1,). '1#.$';"'+18.2(.'<%-21#8 %$ H:#;2$-,,).-18./-01#%2$-,,).\B+29-,#1%.:)8&'0#1[( 67.&#",-$#;#1%.'7.#-$:.'7.%:#.%O'.:)8&'0#1.-%';(.<).%:#.(-;#.0&'+". )2#,8(.$';"'+18(.%:-%.-&#.#1-1%2';#&(A.%:#.%O'.:)8&'0#1(.-&#.$-,,#8. #1-1%2'%'"2$ -18.:-9#.%:#.(-;#.$:#;2$-,.(:27% %'."&'8+$#.'1,).'1#.(201-,. 21.-.EF.*/3?.D:#."&'%'1(.-&#.-,('.$-,,#8.:';'%'"2$? /-01#%2$-,,). #B+29-,#1% Z& F H HFG F &#",-$#;#1% <).i Z& F H HFG i Z& i H HFG F F FGH H F Z& #1-1%2';#&( 4#1-1%2';#&(.:-9#.%:#.(-;#.. ":)(2$-,."&'"#&%2#(.j 827?.<2','02$-,5 /-01#%2$-,,).#B+29-,#1%."&'%'1(.8'.1'%.:-9#.%'.<#.'1.%:#.(-;#. $-&<'1?.Z+%.;+(%.#X"#&2#1$#.%:#.(-;#.;-01#%2$.#192&'1;#1% HFGHFLNHFLHFG /-01#%2$-,,). #B+29-,#1% /-01#%2$-,,). #B+29-,#1% !"# %% H:#;2$-,,).-18./-01#%2$-,,).\B+29-,#1%.:)8&'0#1[( a2-(%#&#'%&'"2$ :)8&'0#1(.-&#.:)8&'0#1(.%:-%.27.&#",-$#8.<).-.0&'+". "&'8+$#(.82-(%#&#';#&(?.D:#(#."&'%'1(.8'.1'%.:-9#.%:#.(-;#.$:#;2$-,. (:27%.-18.029#.&2(#.%'.8277#&#1%.EF.*/3.(201-,(? H, F H H F F &#",-$#;#1% <).i H, F H H i F H, F H H F i a2-(%#&#';#&(.... Z#$-+(#.%:#&#.2(.1'.&'%-%2'1.-&'+18.%:#. 8'+<,#.<'18.%:#."&'%'1.cis %'.%:#.$:,'&21#. 482-(%#&#';#&(.:-9#.8277#&#1%.. ":)(2$-,."&'"#&%2#(5 2(.21.-.8277#&#1%.;-01#%2$.72#,8.7'&;.%:#. "&'%'1.trans %'.%:#.$:,'&21#.-%';? D:#."&'%'1(.'1.HVG. HFG HFG HFG :-9#.8277#&#1%. F H NF &#",-$#;#1% F H NF F H NF $:#;2$-,.(:27%(.-18. <).i O'+,8.029#.%O'. F H F H i H F F i (201-,(A.:'O#9#&. %:#.%O'.(201-,(.;-). HFG HFG HFG <#.9#&).$,'(#.-18. 4!5VLV<+%-1', '9#&,-" a2-(%#&#';#&( !"# %& W:-%.#77#$%.8'#(.-.1#20:<'&210.'&.92$21-,."&'%'1(.:-9#.'1. #-$:.'%:#&c D:#.1+$,#+(.'7.F- 7##,(.<'%:.%:#.-"",2#8.;-01#%2$.72#,8.4Z'5.-18.%:#. a'+<,#% F3 3 H H 3 3 ;-01#%2$.72#,8.'7.%:#.1#20:<'&210.1+$,#+(?..D:#.1#20:<'&210.1+$,#+(.$-1. #2%:#&.8#$&#-(#.'&.21$&#-(#.%:#.;-01#%2$.72#,8.7#,%.-%.%:#.1+$,#+(?..D:2(.2(. $-,,#8.("21V("21.$'+",210 (201-,.+1$'+",#8 7&';.F- (201-,.+1$'+",#8 7&';.F< F< F- F< F< a'+<,#% k-< ("21.F< -,201#8.O2%: ;-01#%2$.72#,8 Z.P.Z' l Z2 S.F< 8#$&#-(#(.(:2#,8210 -%.1+$,#+(.j #-(2#&. %'.7,2".j (:27%#8 8'O172#,8 -1%2"-&-,,#, Z.P.Z' l Z2 V F< 21$&#-(#(.(:2#,8210 -%.1+$,#+(.j :-&8#&. %'.7,2".j (:27%#8 +"72#,8 ("21.F- k<-&#-.+18#&. $+&9#.P.E -1%2"-&-,,#, Z.P.Z' l Z2 V F21$&#-(#(.(:2#,8210 -%.1+$,#+(.j :-&8#&. %'.7,2".j (:27%#8 +"72#,8 -,201#8.O2%: ;-01#%2$.72#,8 Z.P.Z' l Z2 S.F8#$&#-(#(.(:2#,8210 -%.1+$,#+(.j #-(2#&. %'.7,2".j (:27%#8 8'O172#,8 21$&#-(210.;-01#%2$.72#,8.Z' Z'%:.F- -18.F< O'+,8.7'&;.-.8'+<,#%.21(%#-8.'7.-.(210,#."#->. !"# <#$-+(#.%:#).-&#.("21V("21.$'+",#8.O2%:.#-$:.'%:#&? %' !"21V!"21.$'+",210 !"21V("21.(",2%%210.'&.$'+",210.2(.$-+(#8.<).%:#."&#(#1$#.'7. 1'1#B+29-,#1%.92$21-,A.'&.1#20:<'&210."&'%'1(? D:#.(",2%%210.<#%O##1.%:#.%O'."#->(.2(.$-,,#8.%:#.$'+",210.$'1(%-1%.k? Z#$-+(#.$'+",210.2(.$-+(#(.#1%2&#,).<).21%#&1-,.7'&$#(A.%:#.;-012%+8#.'7. %:#.$'+",210.$'1(%-1%.2(.1'%.8#"#18#1%.'1.%:#.;-012%+8#.'7.%:#.-"",2#8. 72#,8?.D:+(A.$'+",210.$'1(%-1%(.-&#.&#"'&%#8.21.:#&%C.-18.O2,,.<#.%:#.(-;#. 1'.;-%%#&.O:-%.%:#.;-012%+8#.'7.%:#.-"",2#8.72#,8.2(A.2?#?.M].'& ^]]./FC? F3 3 H H 3 3 a'+<,#% k-< K'&.-.7&##,).&'%-%210. 1#20:<'&210A.1'1#B+29-,#1%. "&'%'1(.%:#.k.9-,+#.2(. -""&'X2;-%#,)._.FC F< D:#.k-< ;#-1(.%:#. $'+",210.$'1(%-1%.7'&.F(",2%.<).F< '&.92(-.9#&(!"# %( D&2",#% 3 3 F- F< H H 3 F<[ F< -18.F<[ -&#.. ;-01#%2$-,,).#B+29-,#1% (201-,.+1$'+",#8 7&'; FF< F<[ (201-,.+1$'+",#8 7&';.F< F<[ F- k-< k-< ("21.F< -18 F<[ E L E ("21.F&#,-%29#.21%#1(2%) E k<- E 21$&#-(210.;-01#%2$.72#,8.Z' W:-%.O#.(## 1.S.E F- (##(.%O'.... F[(. %&2",#% FD&2",#%% F< F<[ a'+<,#% 1.S.E F< -18.F< (##(. '1#.F. 8'+<,#% -&#-.+18#&. $+&9#.P.E !"# -&#-.+18#&. $+&9#.P.L %) i+-&%#% 3 3 FH H F< F<[[ F<[ F< F<[ -18.F<[[ -&#. ;-01#%2$-,,).#B+29-,#1% (201-,.+1$'+",#8 7&';.F< F<[ F<[[ W#.!## Fi+-&%#% (201-,.+1$'+",#8 7&';.FFF< F<[ F<[[ W#.!## F< F<[ F<[[ a'+<,#% k-< ("21.F< F<[ -18 F<[[ -&#-.+18#&. $+&9#.P.E k-< k-< ("21.F- k<-&#-.+18#&. $+&9#.P.G &#,-%29#... 21%#1(2%) E G G E E E 1.S.E F- (##(.%:&##.... F[(. B+-&%#% 21$&#-(210.;-01#%2$.72#,8.Z' !"# 1.S.E F< F<[ -18. F<[[ (##(.'1#.............. F. 8'+<,#% %* D'."&#82$%.%:#.(",2%%210."-%%#&1.'7.-."&'%'1.'&.0&'+".'7.#B+29-,#1%. "&'%'1(.$'+1%.%:#.1+;<#&.'7.1#20:<'&210."&'%'1(.1'1#B+29-,#1%.%' %:#."&'%'1.21.B+#(%2'1.-18.-88.'1#.41.SE5 D'."&#82$%.%:#.21%#1(2%)."-%%#&1.-.h-($-,[(.%&2-10,#.$-1.<#.+(#8?.D:#. (+;.'7.%:#.1+;<#&(.-<'9#."&'928#(.%:#.21%#1(2%).'7.%:#.(",2%%210 "-%%#&1? (210,#% 8'+<,#% %&2",#% B+-&%#8 B+21%#% (#X%#% E #%$ !"# E E E E E I ^ G M E] E] L G ^ I E E E E E how many times a carbon splits depends on how many protons the adjacent carbons have. the time= protons+1 %+ D&##.82-0&-;( *'%#U !201-,.(",2%%210.2(.1'%.'<(#&9#8 7'&."&'%'1(.%:-%.-&#.$:#;2$-,,). #B+29-,#1%A.:';'%'"2$ '&.#1-1%2'%'"2$?.D:-%.2(A.(201-,.(",2%%210.8'#(.1'%. '$$+&.<#%O##1.$';"'+18(.%:#.:-9#.#X-$%,).%:#.(-;#.$:#;2$-,.(:27%? / / / / . . / / / / D&##.82-0&-;(.-&#.-.%'',.7'&.-1-,)C210.(",2%%210."-%%#&1( F- F< FH H Z& '1,).'1# &#('1-1$# -<('&"%2'1 "#-> k-< P._.FC D&2",#% F- k<- P._.FC i+-&%#% F< F- F< 1'.$'+",210 $'+",210.O2%:.'1#.F< #-$:."#->.7+&%:#&. (",2%.<).$'+",210.O2%:. %:#.'%:#&.F< &-%2' k-< k-< E L k-< E !"# &-%2' E G G E %, H'+",210.'7.*'1#B+29-,#1%.*#20:<'+&( FX F$ F; F$ H F; %&2",#% NHFLHFG H FX k$X k$X k ;X %&2",#% k;X k;X k $; k$; k$; k$; k-< k-< FX F$ F; B+-&%#% k-< k-< k-< k-< k-< k-< k-< k-< !"# &- i+#(%2'1U !:'+,81[%.%:#."&'%'1(.'1.-.$';"'+18.,2>#.#%:),.<&';28#.<#. 1'%.#B+29-,#1%.<#$-+(#.21.%:#.;'(%.(%-<,#.$'17'&;-%2'1.%:#."&'%'1(.O2,,. #X"#&2#1$#.8277#&#1%.;-01#%2$.72#,8( F F F F H H Z& F F F F Z& F F !:'+,81[%.%:#.&#8.:)8&'0#1(.<#.8#(:2#,8#8 ;'&#.%:-1.%:#.<,+#.:)8&'0#1c @%.&'';.%#;"#&-%+&#.%:#.$-&<'1V$-&<'1.(210,#.<'18.&'%-%#(.-""&'X2;-%#,).E. ;2,,2'1.%2;#(.-.(#$'18.-18.%:#.("#$%&';#%#&.2(.%''.(,'O.%'.d(##e %:#.8277#&#1%. $'17&'1%-%2'1(.'7.%:#.;',#$+,#?. 67.-.(',+%2'1.2(.$'',#8.('.%:-%.&'%-%2'1(.-&#.(,'O#8.8'O1.8277#&#1%. $'17'&;-%2'1(.$-1.<#.(##1?.K'&.#X-;",#.$)$,':#X-1#.-%.&'';.%#;"#&-%+&#. '1,).029#(.'1#."#->.<+%.-%.,'O#&.%#;"#&-%+&#(.-.$';",#X.(",2%%210."-%%#&1.2(. '<(#&9#8.<#$-+(#.-X2-,.-18.#B+-%'&2-,."&'%'1(.-&#.1'O.&#(',9#8.8+#.%'.(,'O. 21%#&$'19#&(2'1 <#%O##1.$:-2&.$'17'&;-%2'1(.. F a a a a a a a a F a a a a aE] aE] !"# F a &$ +18#$-8#+%#&2'$)$,':#X-1# &'';.%#;"#&-%+&#.029#(.'1#."#-> VE]]'H.%O'.(201-,(.'7.#B+-,.21%#1(2%).O:2$:. $'&&#("'18(.%'.%:#.-X2-,.-18.#B+-%'&2-,.:)8&'0#1( EAEALV%&2$:,'&'#%:-1#. HFH,LHFLH, H, FF< H H, H FHb H, W:2$:."&'%'1(. ;-01#%2$-,,).#B+29-,#1%c -&#-.&-%2'.+18#&. %:#."#->(.LUE Ha 8'+<,#% L %&2",#% E Hb W:2$:."&'%'1(.-&#. 8#(:2#,8#8 %:#.;'(%c W:-%.2(.%:#.(",2%%210. "-%%#&1c Hb sees 2 protons--> triplet n +1=3 n=2 n +1=2 Ha sees 2 proton---> doublet 8'O1.72#,8 desheilde d +".72#,8 !"# sheilde d &% EV<&';'#%:-1# F- F< FH H Z& HFGHFLZ& -&#-.&-%2'.+18#&. %:#."#->(.GUL G %&2",#% F- F< W:2$:."&'%'1(.-&#. 8#(:2#,8#8 %:#.;'(%c W:-%.2(.%:#.(",2%%210. "-%%#&1c B+-&%#% L !"# && LV$:,'&'"&'"-1# FFFFH F< H H FH, F- 4HFG5LHFH, -&#-.&-%2'.+18#&. %:#."#->(.MUE 8'+<,#% M W:2$:."&'%'1(.-&#. 8#(:2#,8#8 %:#.;'(%c W:-%.2(.%:#.(",2%%210. "-%%#&1c (#"%#% E !"# &' !';#.H'+",210.H'1(%-1%( FX H H m FF< 0#;21-, k-< P.].V G.FC $2( k-X P.M.V E^.FC %&-1( k<X P.EE.V E`.FC H H -,,),2$ H F- k-< P.M.FC F< FF< FX F) '&%:' k-< P.M.V `.FC ;#%- k-X PEVG.FC "-&- k-) P.]VEFC H H F- F< K&##.3'%-%2'1 k-< P._.FC !"# &( \X-;",#( HFGHFLHFLZ& F- F< F$ FH H H Z& -&#-.&-%2'.+18#&. %:#."#->(.GULUL %&2",#% G F- F< F$ W:2$:."&'%'1(.-&#. 8#(:2#,8#8 %:#.;'(%c W:-%.2(.%:#.(",2%%210. "-%%#&1c %&2",#% L (#X%#% L !"# &) H,LFHHFH,HFH,L 8'+<,#% L -&#-.&-%2'.+18#&. %:#."#->(.LUE H, F< H, W:2$:."&'%'1(.-&#. 8#(:2#,8#8 %:#.;'(%c W:-%.2(.%:#.(",2%%210. "-%%#&1c %&2",#% E the side carbons have 2 clorine hence they are more delta positive, so the sidecarbons are more deshelded F- H H H F- H, H, H, !"# &* F- F< F$ N FH H H H NF -&#-.&-%2'.+18#&. %:#."#->(.LULULUE H, F< F$ W:2$:."&'%'1(.-&#. 8#(:2#,8#8 %:#.;'(%c W:-%.2(.%:#.(",2%%210. 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This note was uploaded on 09/15/2010 for the course SCIENCE 267 taught by Professor Sjdifoa during the Winter '09 term at University of Warsaw.

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