Organic Chemistry PKAs

Sulfuric Acid (H2SO4)

-9

Hydroiodic Acid (HI)

-9

Hydrobromic Acid (HBr)

-8

Hydrochloric Acid (HCl)

-7

HF

3.2

Carboxylic acid

4-5

Protonated carbonyls

-7

Protonated alcohols

-4

Protonated ethers

-3

Protonated water (hydronium) (H3O+)

-2

Protonated alcohol on alkene

-2

Thiol

10

Ammonium NH

10

Phenol

10

Water

15-16

Alcohols

16-18

Keton

20

Ester

25

Alkyne

25

Hydrogen (H2)

35

Amines NH2

38

Allylic

40-42

Benzylic

40-42

Aryl

45

Alkene

45

Alkane

50-60

HX

Add X to most substituted carbon

HBr, ROOR

Add Br to the least substituted carbon

H3O+

Add OH to most substituted carbon

1) Hg(OAc)2, H2O

2) NaBH4

Add OH to most substituted carbon

1) BH3 THF

2) H2O2, NaOH

Syn OH at least substituted carbon

H2 Pt High P

Alkene to Alkane

Br2

Anti Br on least and most substituted carbon

Br2, H2O

Anti OH on most substituted carbon and Br on least substituted carbon

1) RCO3H or MCPBA

2) H3O+

Anti Epoxide is made and then OH is on most and least substitued carbon t

KMnO4

NaOH, cold

Syn OH on most and least substituted carbon

1)OsO4

2) NaHSO3

H2O

Syn OH on most and least substituted carbon

1) O3

2) DMS

Unfold ketone and aldehyde

1) xs NaNH2

2) H2O

Alkyne

xs HX

alkyne to alkane and 2 X on most substituted carbon

1) xs NaNH2

2) H2O

Alkane to Alkyne

1) NaNH2

2)RX

Add R to alkyne

H2 Lindlar’s cat.

Cis alkene

H2 pt High P

trans

Na

NH3 (l)

Trans alkene

1) O3

2) H2O

Carboxylic acid and CO2

xs X2

CCl4

4 X two on most and least substituted carbons

X2 (one equiv.)

CCl4

2X one X on most and least substituted carbon alkene

1) R2BH

2) H2O2, NaOH

Aldehyde on least substituted carbon

HgSO4

H2SO4, H2O

Ketone at least substituted carbon and methyl at the end

HX

X on most substituted carbon and alkene

Polar

Uneven distribution of electron density

Nonpolar

Even distribution of electron density

Ionic

Metal vs nonmetal

Linear 180

Trigonal Planar 120

Bent <109.5

Tetrahedral 109.5

Trigonal Pyramidal <109.5