Organic Chemistry 2 Exam 1

chemical shift for CH, CH2, and CH3

1.5 / 1.2 / 0.9

chemical shift for allylic hydrogen (beta to double bond)

1.5-2

chemical shift for hydrogen alpha to C=O carbonyl

2-2.5

chemical shift for benzylic hydrogen

2.2-3

chemical shift for alkynyl (hydrogen next to triple bond)

2-3

chemical shift for hydrogen of alcohol

1-5

chemical shift of hydrogen alpha to a halogen

3-5

chemical shift for hydrogen alpha to oxygen

3.3-5

chemical shift of vinyl hydrogen (alpha to double bond)

4.5-6.5

chemical shift of aryl (alpha to benzene)

6.5-8

chemical shift of aldehyde

9.7

chemical shift of carboxylic acid

10-13

effect on chemical shift for alpha to carbonyl or next to benzene ring

+1.3

effect on chemical shift for alpha to chlorine or bromine

+2.2

effect on chemical shift for alpha to oxygen of alcohol or ether

+2.5

effect on chemical shift for alpha to oxygen of ester

+3

splitting pattern for ethyl

triplet with 3 integration upfield from quartet with 2 integration

splitting pattern for isopropyl

doublet with 6 integration upfield from septet with 1 integration

splitting pattern for tert-butyl

singlet with integration 9

singlet at 9.7 indicates

aldehyde

broad singlet 10-13 indicates

carboxylic acid

chemical shift of methyl for carbon13

10-30 ppm

chemical shift of methylene (secondary carbon) for carbon13

15-55

chemical shift for tertiary or quaternary carbon for carbon13

20-60 ppm

chemical shift for carbon connected to halogen carbon13

20-80

chemical shift for carbon attached to nitrogen carbon13

40-60

chemical shift for carbon attached to oxygen carbon13

40-80

chemical shift for alkynyl (triple bond carbons) carbon13

65-90

chemical shift for alkenyl (double bond carbons) carbon13

100-150

chemical shift for aromatic carbon13

110-170

chemical shift for carbonyl group of carboxylic acid, ester, or amide carbon13

165-185

chemical shift for carbonyl group of aldehyde or ketone carbond13

185-220