OIl O1 OH

1

C it

3067 Quit stretch1717 do stretch

Bose Ce Brs I i

ti H79

Ents Yunis

Motcoat 152 15445

Fok107 ft t109 135 137J f f f 153155

Isotopeeffect lil ratio 2units apart Br

pg t 152

Rule 13

CnHuta CuH2o 27313 152143 CeltzBr 6 7

9 JIEityciaos27879ps Cult't

cytsozBrcheck

units of unsalorationCzH5OzBr 152 T 75

222 1unitof insaf

Irie triplet

0Holt9.9

I gsdxent

AMMI Chemical Environments 3

ppm_ Int Mutt Heofneighborse assignments3 O Z E 2 Ewa Cher

3 7 Z t 2 Ewa CA

g 3 I sfexchanged KottNo cars

O

Hodt cttz cttz B.ir

ECHECHI

011 solventd OH 2

CMR chemical Environments 3

ppg unit H'smC_ Assignment24.3 t 2A CHz

38.6 t 2h cha

178.8 s of Q OH

NSpece.cz sOzBr 152m121 unit of unsaf

Loss OH 17

CO 28

CGH 45

Br 79 81

Ire

F of 3500cm

1717cm I

HNMR3Enx.ae

Hz CHz EwciQ oltexchanges

C 3 Env

0

EWG CHECHEEWG at

g groatsellCHz d O H HHot Kit Ito Br

Br E H HX t

Fits formula Fits formulaC Env C Env

H Env H H Env

IR IRx Hotrar Integration HNMR IntAnwar Mutt Hairarmult

x Conrath Mutt CNrarmult

Spectroscopy*RubricSpectroscopy*RubricSpectroscopy*RubricSpectroscopy*RubricSpectroscopy*RubricSpectroscopy*RubricSpectroscopy*Rubric

Beginning*(0) Developing*(2.6) Adequate*(3) Accomplished*(3.4) Mastery*(4)Mass*Spec

Rule%13/13C%isotope Not*used Rule*13*or*13C*used,*however*error*resulting*in*>±2*carbons*obtained

Rule*13*or*13C*used,*however*error*resulting*in*±2*carbons*obtained*

Rule*13*or*13C*used,*however*error*resulting*in*±1*carbon*obtained Number*of*carbons*calculated*correctly

Mass*Spec

MW Not*Found Incorrect*number*of*carbons*identified,*molecular*formula*does*not*match*molecular*ion*mass

Incorrect*number*of*carbons*identified,*however*molecular*formula*matches*molecular*ion*mass

Correct*number*of*carbons*found,*and*formula*matches*the*molecular*ion*mass,*however*molecular*formula*

incorrect*for*other*reasonsCorrect*Molecular*Formula*Found

Mass*Spec

Isotope%N,X Not*Found Significant*isotope*effects*correctly*interpreted

Mass*Spec

Decomposition%Products Not*Found Few*decomposition*products*calculated,*no*structural*significance*noted

Few*decomposition*products*calculated,*however*significant*misinterpretations*present,*leading*to*significant*

errors*in*corresponding*substructures

Some*decomposition*signals*correctly*identified,*however*minor*misinterpretations*present,*leading*to*minor*errors*

in*corresponding*substructures

Significant*decomposition*signals*correctly*identified*with*corresponding*substructure

IR

Functional%Groups No*determinations*made*or*all*determinations*incorrect Some*functional*groups*determined,*however*significant*misinterpretations*present,*leading*to*significant*errors

Most*functional*groups*determined,*however*significant*misinterpretations*present,*leading*to*significant*errors

Most*functional*groups*determined,*however*minor*misinterpretations*present,*leading*to*minor*errors

All*significant*functional*groups*correctly*identified.**Functional*groups*not*present*identified*as*such.

HNMR

#%Chemical%Environ. No*determination*made Number*of*chemical*environments*incorrectly*identified,*±2*units

Minor*error*in*determination*of*chemical*environments,*±1*unit

Number*of*chemical*environments*determined,*however*determination*is*incorrect*due*to*overlapping*signals*that*

are*difficult*to*interpretNumber*of*chemical*environments*correctly*identified

HNMR

SpinESpin%Coupling No*determinations*made*or*all*determinations*incorrectSome*indication*that*spinOspin*coupling*determinations*

were*used,*however*no*systematic*approach*used,*leading*to*significant*errors

Systematic*determination*of*spinOspin*coupling*used,*however*significant*misinterpretations*present,*leading*to*

significant*errors

Systematic*determination*of*spinOspin*coupling*used,*however*minor*misinterpretations*present,*leading*to*

minor*errors

Splitting*patterns*correctly*identified*and*number*of*neighbors*correctly*determined

HNMR

Integration No*determinations*made*or*all*determinations*incorrectSome*indication*that*integration*values*were*used,*however*no*systematic*approach*used,*leading*to*

significant*errors

Systematic*determination*of*integration*values*used,*however*significant*misinterpretations*present,*leading*to*

significant*errors

Systematic*determination*of*integration*values*used,*however*minor*misinterpretations*present,*leading*to*

minor*errors

Integration*Values*used*to*correctly*determine*the*number*of*hydrogens*giving*rise*to*each*signal

Assignment No*determinations*made*or*all*determinations*incorrectSome*substructure*identification*performed,*no*systematic*

approach*used,*significant*major*errors*made*in*assignments

Systematic*approach*used*in*substructure*identification,*however*significant*misinterpretations*present,*leading*to*

significant*errors*in*assignments

Systematic*approach*used*in*substructure*identification,*however*minor*misinterpretations*present,*leading*to*

minor*errors*in*assignments

All*chemical*signals*correctly*interpreted*into*structural*subunits

CNMR

#%Chemical%Environ. No*determination*made Number*of*chemical*environments*incorrectly*identified,*±2*units

Minor*error*in*determination*of*chemical*environments,*±1*unit

Number*of*chemical*environments*determined,*however*determination*is*incorrect*due*to*overlapping*signals*that*

are*difficult*to*interpretNumber*of*chemical*environments*correctly*identified

CNMR

Assignment No*determinations*made*or*all*determinations*incorrectSome*substructure*identification*performed,*no*systematic*

approach*used,*significant*major*errors*made*in*assignments

Systematic*approach*used*in*substructure*identification,*however*significant*misinterpretations*present,*leading*to*

significant*errors*in*assignments

Systematic*approach*used*in*substructure*identification,*however*minor*misinterpretations*present,*leading*to*

minor*errors*in*assignments

All*chemical*signals*correctly*interpreted*into*structural*subunits

Analysis

Units%of%Unsaturation Not*found Major*error*in*calculation*of*units*of*unsaturation,*±2*units Minor*error*in*calculation*of*units*of*unsaturation,*±1*unit Units*of*unsaturation*determined,*however*a*mathematical *error*results*in*an*incorrect*determination Units*of*unsaturation*correctly*determined

Analysis

Propose%Structures No*structures*proposed A*single*compound*proposed At*least*two*structural*isomers*considered More*than*two*structural*isomers*considered All*reasonable*structural*isomers*considered

Analysis

Structure%determination No*analysis*completed*on*proposed*structuresAnalysis*performed*on*single*compound*overlooking*major*

flaws*in*proposed*structure*leading*to*an*incorrect*determination

Analysis*performed*on*multiple*structural*isomers,*however*major*inconsistencies*between*spectroscopic*data *and*proposed*structures*overlooked*leading*to*an*incorrect*

determination

Analysis*performed*on*multiple*structural*isomers,*however*minor*inconsistencies*between*spectroscopic*data*and*proposed*structures*overlooked*leading*to*an*incorrect*

determination

Proposed*structures*analyzed*to*correctly*determine*the*compound*in*question

tropylium 206M 208ion 79t

EI EI Aa

Hat90m12 Aromatic

I

put 206

Base 206Molecule aromatic

3Isotope Br

forJason

Riders15 Cis 26 JBL31206 6h7195 206I CgHigBrzIzH 79867120

CHzBr KLx 86 to

CioltzBr

no oh

NO0

Hydrocarbon 4

S d d tid t's

I 4 6 4DetailanisetEt

it NMR

Ar

gµ

of H's 7 of Enea 6

7 25 ZH ZEN Mutt Ar

7 3 IH d Ar7.48 IH d Ar7 50 l It Ar

Ar7 58 IH o

7.78 IH S Ar

detail

of C Env to yNosymmetry

ppm_ Assignment119.4 C Br

7126.2

i far129 2129 429 9131 7 Ar EWG134 y

GoltzBr

21

7142L7 units ofunsafe

IF GoHoo

tBr

ii