Prepared by: Lau Tiing Kiek Teoh Wenjia 2PPRP4T-SN

hydroxyl group makes the alcohol molecule polar. forms hydrogen bonds to one another and to other compounds. Methanol, ethanol, and propanol miscible in water hydroxyl group wins out over the short carbon chain. Butanol moderately soluble theres a balance between the two trends. Alcohols of five or more carbons (Pentanol and higher) effectively insoluble in water because of the hydrocarbon chain's dominance. All simple alcohols are miscible in organic solvents.

hydrogen bonding alcohols tend to have higher boiling points than comparable hydrocarbons and ethers. Can show either acidic or basic properties at the O-H group. Alcohols can also undergo oxidation: aldehydes, ketones, carboxylic acids. dehydration: alkenes. nucleophilic substitution reactions: after enzymatic activation. (the lone pairs of electrons on the oxygen of the hydroxyl group also makes alcohols nucleophiles.) other reactions: form ester compounds.

PREPARATION OF ALCOHOL
1. Fermentation
Ethanol for use in alcoholic beverages, and the vast majority of ethanol for use as fuel, is produced by fermentation. When certain species of yeast, most importantly, Saccharomyces cerevisiae, metabolize sugar in the absence of oxygen, they produce ethanol and carbon dioxide. The chemical equation below summarizes the conversion: C6H12O6
Zymase

2CH3 CH2 OH + 2CO2

Industrial Preparation of Ethanol

Ethene and steam are passed over phosphoric acid catalyst at 330C under high pressure of 6 Mpa to produce ethanol.
H3PO4 acid

CH2 = CH2 + H2O

CH3CH2OH

2. Hydration of alkenes
CH2 C CH3 CH3

+ H

CH 3 HOH CH3

electrophilic addtion:
OH

C
CH 3

Markovnikov rule

3. Reduction from
NaBH 4

(1) Aldehyde (2) ketone

RCHO

( or LiAlH4 ) NaBH 4

RCH 2 OH

RCOR'

RCH(OH)R'

( or LiAlH4 ) (3) Carboxylic acid O H+ LiAlH 4 (19-11) R C OH

O LiAlH 4 / (CH 3 CH2 ) 2 O H

R C H2OH

OH

+ H ,

H2 O

Isopropyl alcohol solvent for paints and chemical processes. used as a beverage (ethanol only), as fuel and for many scientific, medical, and industrial utilities. ethanol and methanol, can be used as an Alcohol fuel ethanol can be used as a solvent in medical drugs, perfumes, and vegetable essences such as vanilla

Ethanol antiseptic to disinfect the skin before injections are given, often along with iodine. Ethanol-based soaps are becoming common in restaurants and are convenient because they do not require drying due to the volatility of the compound. Alcohol preservative for specimens. Glycerol possesses good moisturizing properties, so about 50% of the amount produced goes into foods and cosmetics.

Ether is a class of organic compounds which contain an ether group an oxygen atom connected to two (substituted) alkyl or aryl groups of general formula ROR'.

Simple ethers are volatile, flammable liquids. Slightly soluble (low MW) in water Dipolar, so - tend to be higher boiling than hydrocarbons of the same mass. - good at dissolving many organic compounds. Low reactivity towards many reagents makes them good solvents for chemical reactions.

Cyclic ethers such as tetrahydrofuran and 1,4-dioxane are totally miscible in water because of the more exposed oxygen atom for hydrogen bonding as compared to aliphatic ethers.

Preparation of Ethers
The Williamson Synthesis of Ethers
- prepare unsymmetrical ethers where the alkyl groups are not the same. -The reaction involves an SN2 reaction in which an alkoxide ion replaces a halogen,sulfonyl, or sulfate group. Usually, alkyl halides are used. -The alkoxide can be prepared by the reaction of the corresponding alcohol with an active metal such as metallic Sodium or the use of a metal hydride like NaH acting upon the alcohol. The resulting alkoxide salt is then reacted with the alkyl halide (sulfonate or sulfate) to produce the ether in an SN2 reaction. See Fig 3 below)

MECHANISM FOR ALCOHOL CONDENSATION TO GIVE AN ETHER

Step 1: An acid/base reaction. Proton donation of the alcoholic oxygen to make a better leaving group. This step is very fast and reversible. The lone pairs on the oxygen make it a Lewis base. Step 2: The O of the second alcohol molecule functions as the nucleophile and attacks to displace the good leaving group, a neutral water molecule, by cleaving the C-O bond. This creates an oxonium ion intermediate. Step 3: Another acid / base reaction. The proton is removed by a suitable base (here a water molecule, ROH is another alternative) to give the ether product.

Diethyl ether is a common laboratory solvent. has a high cetane number of 85 - 96 and is used as a starting fluid for diesel and gasoline engines because of its high volatility and low autoignition temperature.

Modern anesthetic agents, such as methyl propyl ether (Neothyl) and methoxyflurane (Penthrane) reduce side effects such as postanesthetic nausea and vomiting.

Ether, mixed with ethanol, was marketed in the 19th century as a cure-all and recreational drug, during one of Western society's temperance movements. At the time, it was considered improper for women to consume alcoholic beverages at social functions, and sometimes ethercontaining drugs would be consumed instead Due to its immiscibility with water and the fact that non-polar organic compounds are highly soluble in it, ether is also used in the production of freebase cocaine.

Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups.

The boiling point of amines is higher than those of the corresponding phosphines, but generally lower than those of the corresponding alcohols. Methyl-, dimethyl-, trimethyl-, and ethylamine are gases under standard conditions, whereas diethylamine and triethylamine are liquids. Most other common alkyl amines are liquids; highmolecular-weight amines are, of course, solids.

Gaseous amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" smell. Most aliphatic amines display some solubility in water, reflecting their ability to form hydrogen bonds. Solubility decreases with the increase in the number of carbon atoms, especially when the carbon atom number is greater than 6. Aliphatic amines display significant solubility in organic solvents, especially polar organic solvents. Primary amines react with ketones such as acetone, and most amines are incompatible with chloroform and carbon tetrachloride.

Preparation of Amine
(1) Alkylation from ammonia or other amines
C H3 N H2 C H3 Br
(C H ) NH 3 2

C H3 Br
(C H ) N 3 3

C H3 Br

(C H ) N Br 3 4

(2) From alkyl halide:

RX

+ CN

RC

+X

RC

LiAlH4

R C H2 NH 2

(3) Reduction from amides:

O LiAlH 4 NH CH 3 NH CH 3

H H

24

1. Hofmann's method This reaction takes place in a sealed tube at a temperature of about 100C and a mixture of primary, secondary and tertiary amines is obtained. CH3I + NH3 CH3NH2 + HI CH3NH2 + CH3I( CH3)2NH+ HI (CH3)2NH+ CH3I( CH3)3N+ HI (CH3)3N + CH3I(CH3)4NIIf excess of alcoholic ammonia is used in the reaction, primary amine is the main product and if alkyl halide is used in excess, tertiary amine is the main product.

2. From alcohol A mixture of primary, secondary and tertiary amines is obtained when a mixture of alcohol vapour and ammonia is passed over heated Alumunia or Thoria at 350C. C2H5OH+ NH3 C2H5NH2 + H2O C2H5NH2 + C2H5OH (C2H5)2NH + H2O (C2H5)2NH + C2H5OH(C2H5)3N + H2O

Dyes Primary aromatic amines are used as a starting material for the manufacture of azo dyes. It reacts with nitric(III) acid to form diazonium salt, which can undergo coupling reaction to form azo compound. As azo-compounds are highly coloured, they are widely used in dyeing industries, such as: Methyl orange Direct brown 138 Sunset yellow FCF Ponceau

Drugs Chlorpheniramine antihistamine that helps to relieve allergic disorders due to cold, hay fever, itchy skin, insect bites and stings. Chlorpromazine tranquillizer that sedates without inducing sleep. It is used to relieve anxiety, excitement, restlessness or even mental disorder.

Product Name : Heineken (alcoholic beverages) Name of Chemicals : Ethanol Chemical Type : Alcohol

Product Name : Spray duster (aerosol propellants)

Name of Chemicals : Dimethyl Ether (DME) Chemical Type : Ethers

Product Name : Hayleve (drugs) Name of Chemicals : Chlorphenamine maleate

(CPM; Chlor- Trimeton, Piriton, Chlor-Tripolon)

Chemical Type : Amine