Assign the peak groups for the structure below:


Below is a portion the spectrum of 2-methyl-3-buten-2-ol:

Use the table of data below:

Substituent Effects on Chemical Shifts of Protons on a C=C

This is an abbreviated list taken from the very robust database at

http://www.chem.wisc.edu/areas/reich/handouts/nmr-h/hdata%7B05%7D.gif

accessed on November 27, 2012.

All credit for this work goes to Hans J. Reich. The intent of this selection is to give learners a feel for how the proton environment effects the chemical shift. This particular set applies to protons on a C=C double bond. The base shift of 5.25 is from a proton in unsubstituted ethene. Substituent effects to the chemical shift are added or subtracted to 5.25 per the data below. Be aware, for the most part these are empirical calculations. There are many compounds that are exceptional to such calculations and give very different chemical shifts. Although frustrating, that's what makes science fun!

Substituent	geminal	cis	trans
OR	1.22	-1.07	-1.21
Cl	1.08	0.18	0.13
OC(O)-R	2.11	-0.35	-0.64
CH2X (X=F,Cl,Br)	0.70	0.11	-0.04
R (alkyl)	0.45	-0.22	-0.28
CH2OH	0.64	-0.01	-0.02
CMe2OH	0.74	-0.05	-0.22
CH2NR2	0.58	-0.10	-0.08
NR2	0.80	-1.26	-1.21
CN	0.27	0.75	0.55

Assign the peak groups for the structure below:


Below is a portion the spectrum of ethyl vinyl ether:

Use the table of data below:

Substituent Effects on Chemical Shifts of Protons on a C=C

This is an abbreviated list taken from the very robust database at

http://www.chem.wisc.edu/areas/reich/handouts/nmr-h/hdata%7B05%7D.gif

accessed on November 27, 2012.

All credit for this data goes to Hans J. Reich. The intent of this selection is to give learners a feel for how the proton environment effects the chemical shift. This particular set applies to protons on a C=C double bond. The base shift of 5.25 is from a proton in unsubstituted ethene. Substituent effects to the chemical shift are added or subtracted to 5.25 per the data below. Be aware, for the most part these are empirical calculations. There are many compounds that are exceptional to such calculations and give very different chemical shifts. Although frustrating, that's what makes science fun!

Substituent	geminal	cis	trans
OR	1.22	-1.07	-1.21
Cl	1.08	0.18	0.13
OC(O)-R	2.11	-0.35	-0.64
CH2X (X=F,Cl,Br)	0.70	0.11	-0.04
R (alkyl)	0.45	-0.22	-0.28
CH2OH	0.64	-0.01	-0.02
CMe2OH	0.74	-0.05	-0.22
CH2NR2	0.58	-0.10	-0.08
NR2	0.80	-1.26	-1.21
CN	0.27	0.75	0.55

Assign the peak groups for the structure below:


Below is a portion the spectrum of isoprenyl methyl ether:

Use the table of data below:

Substituent Effects on Chemical Shifts of Protons on a C=C

This is an abbreviated list taken from the very robust database at

http://www.chem.wisc.edu/areas/reich/handouts/nmr-h/hdata%7B05%7D.gif

accessed on November 27, 2012.

All credit for this data goes to Hans J. Reich. The intent of this selection is to give learners a feel for how the proton environment effects the chemical shift. This particular set applies to protons on a C=C double bond. The base shift of 5.25 is from a proton in unsubstituted ethene. Substituent effects to the chemical shift are added or subtracted to 5.25 per the data below. Be aware, for the most part these are empirical calculations. There are many compounds that are exceptional to such calculations and give very different chemical shifts. Although frustrating, that's what makes science fun!

Substituent	geminal	cis	trans
OR	1.22	-1.07	-1.21
Cl	1.08	0.18	0.13
OC(O)-R	2.11	-0.35	-0.64
CH2X (X=F,Cl,Br)	0.70	0.11	-0.04
R (alkyl)	0.45	-0.22	-0.28
CH2OH	0.64	-0.01	-0.02
CMe2OH	0.74	-0.05	-0.22
CH2NR2	0.58	-0.10	-0.08
NR2	0.80	-1.26	-1.21
CN	0.27	0.75	0.55

Assign the peak groups for the structure below:


Below is a portion the spectrum of vinyl acetate:

Use the table of data below:

Substituent Effects on Chemical Shifts of Protons on a C=C

This is an abbreviated list taken from the very robust database at

http://www.chem.wisc.edu/areas/reich/handouts/nmr-h/hdata%7B05%7D.gif

accessed on November 27, 2012.

All credit for this data goes to Hans J. Reich. The intent of this selection is to give learners a feel for how the proton environment effects the chemical shift. This particular set applies to protons on a C=C double bond. The base shift of 5.25 is from a proton in unsubstituted ethene. Substituent effects to the chemical shift are added or subtracted to 5.25 per the data below. Be aware, for the most part these are empirical calculations. There are many compounds that are exceptional to such calculations and give very different chemical shifts. Although frustrating, that's what makes science fun!

Substituent	geminal	cis	trans
OR	1.22	-1.07	-1.21
Cl	1.08	0.18	0.13
OC(O)-R	2.11	-0.35	-0.64
CH2X (X=F,Cl,Br)	0.70	0.11	-0.04
R (alkyl)	0.45	-0.22	-0.28
CH2OH	0.64	-0.01	-0.02
CMe2OH	0.74	-0.05	-0.22
CH2NR2	0.58	-0.10	-0.08
NR2	0.80	-1.26	-1.21
CN	0.27	0.75	0.55

Assign the peak groups for the structure below:




Below is a portion the proton NMR spectrum of trans-1,3-dichloropropene:


Use the table of data below:

Substituent Effects on Chemical Shifts of Protons on a C=C

This is an abbreviated list taken from the very robust database at

http://www.chem.wisc.edu/areas/reich/handouts/nmr-h/hdata%7B05%7D.gif

accessed on November 27, 2012.

All credit for this data goes to Hans J. Reich. The intent of this selection is to give learners a feel for how the proton environment effects the chemical shift. This particular set applies to protons on a C=C double bond. The base shift of 5.25 is from a proton in unsubstituted ethene. Substituent effects to the chemical shift are added or subtracted to 5.25 per the data below. Be aware, for the most part these are empirical calculations. There are many compounds that are exceptional to such calculations and give very different chemical shifts. Although frustrating, that's what makes science fun!

Substituent	geminal	cis	trans
OR	1.22	-1.07	-1.21
Cl	1.08	0.18	0.13
OC(O)-R	2.11	-0.35	-0.64
CH2X (X=F,Cl,Br)	0.70	0.11	-0.04
R (alkyl)	0.45	-0.22	-0.28
CH2OH	0.64	-0.01	-0.02
CMe2OH	0.74	-0.05	-0.22
CH2NR2	0.58	-0.10	-0.08
NR2	0.80	-1.26	-1.21
CN	0.27	0.75	0.55