Organic Functional Groups. Functional Groups See CD-ROM Screens 11.5 & 11.6 Alcohols Ethers Aldehydes Ketones Acids Amines.

OrganicFunctional

Groups

Functional Groups

See CD-ROM Screens 11.5 & 11.6See CD-ROM Screens 11.5 & 11.6See CD-ROM Screens 11.5 & 11.6See CD-ROM Screens 11.5 & 11.6

AlcoholsEthersAldehydesKetonesAcidsAmines

Alcohols are a derivative of water Many alcohols dissolve in water

Methanol dissolves in

water.

Methanol dissolves in

water.

Butanol is NOT soluble in water.

Butanol is NOT soluble in water.

O

HH

methyl alcohol (methanol)

O

CH3H

ethyl alcohol (ethanol)

O

CH2CH3H

n-propyl alcohol (1-propanol)

O

CH2CH2CH3H

O

CHHCH3

H3C

2-propyl alcohol (isopropanol)

an ALCOHOLR – OH

Name: add – ol to name of hydrocarbon

Indicate position of -OH with number

TYPES OF ALCOHOLSTYPES OF ALCOHOLS

R C OH

H

H

R C OH

R

H

R C OH

R

R

CH3CH2OH, ethanol

rubbing alcohol H3C C OH

CH3

H

Primary

Secondary

Tertiary

GLYCOLSGLYCOLSAlcohols with Two OH GroupsAlcohols with Two OH Groups

Propylene Propylene glycolglycol

EthyleneEthylene glycolglycol

Sugars: Related to AlcoholsSugars: Related to AlcoholsSugars are carbohydrates, cmpds

with the formula Cx(H2O)y.

O

H

HO

H

HO

HOHH

OH

OHCHO

OHH

HHO

OHH

OHH

CH2OH

O

H

HO

H

HO

OHOHH

H

OH

1

23

4 5

12

3

45

1

2

3

4

5

-D-glucose -D-glucose

Open chain form

H H

Ethers are another derivative of water

Many ethers dissolve in water

diethyl ether

O

CH2CH3H3CH2C

ethylmethyl ether

O

CH2CH3H3C

an ETHER

R - O - R’

Compounds with Compounds with Carbonyl GroupCarbonyl Group

AldehydeAldehydeAldehydeAldehyde Carboxylic acidCarboxylic acidCarboxylic acidCarboxylic acid KetoneKetoneKetoneKetone

O

C

methanalFORMALDEHYDE

O

C

HH

propanal

O

C

CH2CH3H

O

C

HR

an ALDEHYDEName: add – al to name of hydrocarbon

O

C

HR

CinnamaldehydeCinnamaldehyde

Odors from Odors from aldehydes and aldehydes and

ketonesketones

O

C

CH3H3C

dimethylketonepropanoneACETONE

2-pentanone

O

C

CH2CH2CH3H3C

3-pentanone

O

C

CH2CH3H3CH2C

O

C

R’R

O

C

R'R

a KETONEName: add – one to name of hydrocarbonIndicate position of =O with number

Carboxylic AcidsCarboxylic Acids

Benzoic Benzoic acidacid

Carboxylic acid Carboxylic acid group with acidic group with acidic

HH++

All are All are WEAKWEAK acids acids

Acetic acidAcetic acid

Acids are found in Acids are found in many natural many natural substances: bread, substances: bread, fruits, milk, winefruits, milk, wine

Acids are found in Acids are found in many natural many natural substances: bread, substances: bread, fruits, milk, winefruits, milk, wine

methanoic acidFORMIC ACID

HCOOH, HCOOH, gives the gives the sting to sting to

ants.ants.

HCOOH, HCOOH, gives the gives the sting to sting to

ants.ants.

O

C

HHO

ethanoic acidACETIC ACID

O

C

OHH3C

butanoic acidBUTYRIC ACID

O

C

CH2CH2CH3HO

a CARBOXYLIC ACIDName: add – oic to name of

hydrocarbon + acid

O

C

RHO

While alcohols are derivatives of H2O

(R–OH), amines are derivatives of NH3.

Methylamine

Dimethylamine

Trimethylamine

NH

HH

Amines generally have Amines generally have terrible odors!terrible odors!

Cadaverine

PyridinePyridine

Amines, like NH3, are bases

2 C6H5NH2(aq) + H2SO4(aq) 2 C6H5NH3+(aq) + SO4

2- (aq)

NH2

+ H2SO4

NH3+

+ SO42-

aniline anilinium ion

Many natural products and drugs (such as nicotine and cocaine)

are bases.

NicotineNicotineH+

C C

H

H2N

R

OH

O

an AMINO ACID

GlycerolGlycerolAlcohol with 3 OH GroupsAlcohol with 3 OH Groups

Combine this with long chain acids Combine this with long chain acids ??? ???Fatty acids Fatty acids fats and oils fats and oils

Combine this with long chain acids Combine this with long chain acids ??? ???Fatty acids Fatty acids fats and oils fats and oils

Fats and OilsFats and Oils

R = organic group R = organic group with with NONO C=C bonds C=C bondsCC1212 = Lauric acid = Lauric acid

CC1616 = Palmitic acid = Palmitic acid

CC1818 = Stearic acid = Stearic acid

R = organic group R = organic group with with NONO C=C bonds C=C bondsCC1212 = Lauric acid = Lauric acid

CC1616 = Palmitic acid = Palmitic acid

CC1818 = Stearic acid = Stearic acid

O

O

O

H2C

HC

H2C

CRO

CRO

CR

O

R = organic R = organic group with C=C group with C=C

bondsbondsCC1818 = oleic acid = oleic acid

R = organic R = organic group with C=C group with C=C

bondsbondsCC1818 = oleic acid = oleic acid

What is the What is the functional functional

groupgroup in a fat in a fat or oil?or oil?

What is the What is the functional functional

groupgroup in a fat in a fat or oil?or oil?

Fats and OilsFats and OilsO

O

O

H2C

HC

H2C

CRO

CRO

CR

O

Fats with C=C bonds are usually Fats with C=C bonds are usually LIQUDSLIQUDS

Fats with C=C bonds are usually Fats with C=C bonds are usually LIQUDSLIQUDS

Oleic acid: a Oleic acid: a monounsaturatmonounsaturated fatty acid ed fatty acid

Oleic acid: a Oleic acid: a monounsaturatmonounsaturated fatty acid ed fatty acid

C=C bondC=C bondC=C bondC=C bond

Fats and OilsFats and Oils

Fats with saturated acids Fats with saturated acids (no C=C bonds) are (no C=C bonds) are

SOLIDS.SOLIDS.

Fats with saturated acids Fats with saturated acids (no C=C bonds) are (no C=C bonds) are

SOLIDS.SOLIDS.

O

O

O

H2C

HC

H2C

CRO

CRO

CR

O

Saturated fats Saturated fats are more are more

common in common in animals. animals.

Saturated fats Saturated fats are more are more

common in common in animals. animals.

Fats and Polar Fats and Polar BearsBears

•Bears gorge on blubber in the Bears gorge on blubber in the winter.winter.•During the summer bears rely on During the summer bears rely on stored fat for energy.stored fat for energy.•Burn 1-1.5 kg of fat per day.Burn 1-1.5 kg of fat per day.•Water for metabolism comes Water for metabolism comes from fat burning.from fat burning.

•Bears gorge on blubber in the Bears gorge on blubber in the winter.winter.•During the summer bears rely on During the summer bears rely on stored fat for energy.stored fat for energy.•Burn 1-1.5 kg of fat per day.Burn 1-1.5 kg of fat per day.•Water for metabolism comes Water for metabolism comes from fat burning.from fat burning.

Trans Fatty AcidsTrans Fatty Acids•Oleic acid is a mono–Oleic acid is a mono–unsaturated unsaturated cis-cis-fatty acidfatty acid•Trans fatty acids have Trans fatty acids have deleterious health effects. deleterious health effects. •Trans fatty acids raise plasma Trans fatty acids raise plasma LDL cholesterol and lower HDL LDL cholesterol and lower HDL levels.levels.

CHCH33(CH(CH22))77CH=CH(CHCH=CH(CH22))77COCO22H H

Trans Fatty AcidsTrans Fatty Acids

Food Percentages of Food Percentages of Trans-Fatty AcidsTrans-Fatty Acids

ButterButter 3.63.6

Soft MargarineSoft Margarine 5.25.2

Hard MargarineHard Margarine 12.412.4

Vegetable Oils, Including Vegetable Oils, Including Safflower, Sunflower, and Safflower, Sunflower, and SoySoy

00

Beefburger, Fried or Beefburger, Fried or GrilledGrilled

0.80.8

Chocolate Cake with IcingChocolate Cake with Icing 7.17.1