B. Alcohols R—OH

Functional Group = hydroxyl group = OH

Alcohol names all end in –ol. Numbers tell which C atom the OH is attached to.

Ex: 1-propanol

OHH

H

H

C

H

H

C

H

H

C

The OH group makes alcohols polar.

Alcohols dissolve in water because H2O is polar:

parent: propanemolecular: C3H7OHempirical: C3H8Ostructural: CH3CH2CH2OH

HO

H

-+

OH+

Because it has 1 OH, it is a monohydroxy alcohol

Compare: Alcohols BasesOH group: covalently attached an ion in solutionelectrolyte: no yeswater soluble… yes yesbecause…. OH is polar OH- is ion

Ex. 1,2-ethanediol is a dihydroxy alcohol (two OH groups)

Ex. 1,2,3-propanetriol is a trihydroxy alcohol (three OH groups)

OH

OH

H

H

C

H

C H

OH

OH

(akaethyleneglycol)

(akaglycerol)

OH

H

H

C

H

C H

H

C

ethylene glycol

Ethylene glycol is widely used as an automotive antifreeze and a precursor to polymers. In its pure form, it is an odorless, colorless, syrupy, sweet-tasting liquid. Ethylene glycol is toxic, and ingestion can result in death.

OH

OH

H

H

C

H

C H

Glycerin (glycerol):--> clear, sweet tasting, oily liquid--> used to keep dried fruits and pastry fillings moist, in toothpaste, hand creams, eye and ear drops,suppositories (for laxatives, eg), and as an antifreeze

H2SO4 for drying

aka nitroglycerin(dynamite)Also:

glycerin + nitric acid --> glycerol trinitrate

Ex. ethanol (ethyl alcohol) = drug, solvent, fuelparent: ethanemolecular: C2H5OHempirical: C2H6Ocondensed: CH3CH2OH

OHH

H

H

C

H

H

C

Ex. Alcohols can also be classified as:

1/ primary: OH attached to an end C as in ethanol

2/ secondary: OH is attached to a C that is directly attached to two other C atoms. At right: 2-butanol

3/ tertiary: OH is attached to a C that is directly attached to threeother C atoms At right: 2-methyl, 2-propanol

HH

H

H

C

H

H

C

H

C

H

H

C

OH

H

H

H

C

H

H

C

H

C

OH

H

C HH

Ex. For each example below, give the name. Circle if a mono-, di-, or trihydroxy and if a primary, secondary or tertiary alcohol.

1/ 3/

name: _________________ name: ________________

type: mono- di- tri- type: mono- di- tri-

class: prim. sec. tert. class: prim. sec. tert.

2/ 4/

name: _________________ name: ________________

type: mono- di- tri- type: mono- di- tri-

class: prim. sec. tert. class: prim. sec. tert.

OHH

H

H

C

K OH K OHOH K OH KK OH K OH

OH K OH K

HH

H

H

C

H

H

C

H

C

H

H

C

OH

H

C

H

C

OH

OH

H

H

H

C C

H

C

H

OH

H

C HH

H

H

H

C

H

H

C

methanol

3-methyl, 2-pentanol

KOH

2,3,4-hexanetriol

C. Ethers - two C chains joined by an oxygen O “bridge”Formula: R—O—R‘

Name: (name R without -ane) + oxy + name of R‘

Ex. methoxymethane aka: dimethyl ethermolecular: C2H6Ocondensed: CH3OCH3

Ex. methoxyethane aka: methyl ethyl ethermolecular: C3H8Ocondensed: CH3OCH2CH3

O HH

H

H

C

H

H

C

O

H

H

C HH

H

H

C

H

H

C

Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages in carbohydrates and lignin.

HH

H

H

C HH

O

C

HH

H

H

C

H

H

C

H

O

C

D. Aldehydes: When a carbonyl group (—C=O) replaces the CH2 at the end of a hydrocarbon

Formula R—C—H Name: replace –e with –al

Ex. methane: methanal: aka: formaldehyde molecular: CH2O

structural: HCOH

Ex. ethane: ethanal: aka: acetaldehyde molecular:

C2H4O

structural: CH3COH

or: CH3

O

O

CH

H

H

C H

Formaldehyde was the first polyatomic organic molecule detected in the interstellar medium[6] and since its initial detection has been observed in many regions of the galaxy.

Carbonyl group:C=O

Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part of their normal metabolism. It is also produced by oxidation of ethanol and is popularly believed to be a cause of hangovers.[2]

Carbonyl group:C=O

E. Ketones: When a carbonyl group (—C=O) replaces a C in the interior of a hydrocarbon:

Formula: R—C—R' Name: replace –e with –oneEx. propane: propanone: aka: acetone

molecular: C3H6Ocondensed: CH3COCH3

or: CH3CCH3

Ex. Isomers: 2-pentanone and 3-pentanone:

condensed: CH3CHOCH2CH2CH3 CH3CH2CHOCH2CH3

C

O

HH

H

H

C

H

H

C

H

H

C H

H

H

C H

H

H

CO

HH

H

H

C

H

H

C

H

H

C

H

H

H

C C

O

HH

H

H

H

H

C

H

H

C

H

C

H

H

C C

O

O

The word ketone comes from the word: acetone

Ketones are produced on massive scales in industry as solvents, polymer precursors, and pharmaceuticals.

F. Organic Acids are formed by adding the carboxyl group –COOH to a hydrocarbon chain. They are weak acids andweak electrolytes, and are known as carboxylic acids

Functional group = --COOH = —C—OH

Name: replace –e with –oic acid

Ex. ethanoic acid (aka acetic acid in vinegar):

molecular: HC2H3O2

condensed: CH3COOH

or:CH3

O

HH

H

H

C

H

H

C H

H

H

C C —OH

O

ethane: ethanoicacid:

OC—OH

Ex. A fatty acid is a carboxylic acid –COOH with a long unbranched hydrocarbon chain “tail.”

Saturated fatty acids:-single C-C bonds -pack closely-solids at room temp-animal “fats”

Unsaturated fatty acids:-double C=C bonds bend up the tail-liquids at room temp-vegetable “oils”

the “fatty” tail the acid

Fats and oils are triglycerides. They are formed when the alcohol glycerol combines with 3 fatty acids by condensing out water.

benzoic acid

Used in toothpastes, mouthwashes,cosmetics and deodorants for its antimicrobial properties

--COOH

ascorbic acid – Vitamin C

--COOH

G. Esters have the functional group: General formula:

They are the result of an esterification reaction: organic + alcohol water + ester

acidEx.

Sulfuric acid (H2SO4) is used as a catalyst and as a dehydrating agent to remove the water, which is why this is sometimes called condensation reaction.

H2SO4

alcohol + acid…es terrifying!

+

Notice: In the general formula:

Naming: The alkyl name of the alcohol is added to the acid group modified to end in –oate or -ate

Esters have strong, fragrant aromas and are thecause of the odors and flavors of pineapple, banana,wintergreen and oranges.

Ex. The smell of pineapples is due to ethyl butyrate

ethanol + butanoic acid water + ethyl butyrate(alcohol) (ester)

this part comesfrom the acid

this part is from the alcohol

ethanol + butanoic acid water + ethyl butyrate(alcohol) (ester)

From the acid:

From the alcohol:

acid:

alcohol:

octanol + acetic acid water + octyl acetate(alcohol) (ester)

From the acid:

From the alcohol:acid:

alcohol: