Functional Groups, PKA and IR Spectra

HI

Hydroiodic acid (Hydrogen Iodide):

 

[image]

 

pKa: -10

 

 

HCl

Hydrochloric Acid:

 

pKa: -8

Benzene sulfonic acid
[image] pKa: -6.5
Sulfuric Acid
[image] pKa: -3
Hydronium Ion

H+

 

pKa: -1.7

HF

Hydrofluoric Acid

 

pKA: 3.2

H2S

Hydrogen Sulfide

 

pKa: 7

HCN

Hydrogen cyanide

 

[image] Nitrile functional group

PKA: 9.3

methanethiol

CH3SH

 

pKa: 10.3

menthanol

CH3

pKa: 16

Ammonia

NH3

 

pKa: 36

alkene

carbon-carbon double bond

 

one degree of unsaturation

 

pKa: ~ 43

HBr

Hydrobromic Acid

 

pKa: -9

Conjugate acid of acetic acid

[image]

 

 

pKa: -6

Conjugate acid of dimethyl ether
pKa: -3.5
Conjugate acid of ethanol
pKa: -2.4
HNO3

Nitric Acid

 

pKa: -1.5

NH4+

Ammonium ion

 

pKa 9.3

phenol
[image] pKa: 10
pKa of water
15.7
Alkyne

[image]

pKa: 25

 

2 degrees of unsaturation

hydrogen gas
pka: 40
alkane

pka: ~ 60

 

 

OH group

Carboxyl group

 

Alcohol

Amine
[image]
Structure of ether functional group
[image]
Thiol
[image]
Sulfide
[image]
Aryl
Phenol
[image]
Epoxide
[image]
Aldehyde
[image]
Ketone
[image]
Carboxylic Acid
[image]
Ester
[image]
Acid chloride
[image]
Anhydride
[image]
Amide
[image]
thioester
[image]
Nitrile
[image]
Peroxide
[image]
peracid
[image]
What is the method for determining the structure from an IR?
determine the functional groups
what is the fingerprint region?
0-1500

Where do we find a carbonyl?

[image]

1600-1800 cm-1
Where will you find an sp2-H bond?

an alkene or a beneze:

[image]3100

What is an sp-H bond and where will you find it?

An alkyne

 

3200-3300

 

What is an sp3-H bond and where will you find it?

An alkane

3000-3100

 

Where is an OH group located?
3300-3500
Where is an NH group located?
3300-3500
How do you determine the difference between an OH group and an NH group?

Both are found in 3300-3500

 

The OH is broad and smoothly curved; the NH is jagged

What is the Index of Hydrogen Deficiency?
1/2{([2 x #C] – [#H + #X]) – #N +2}
What is the degree of unsaturation for a benzene ring?
1
What is the degree of unsaturation for an alkene

C=C

1 degree of unsaturation

CnH2n

What is the degree of unsaturation for an alkyne?

2 degrees of unsaturation

 

CnH2n-n

x

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