CONTENT

 Alcohol

 Treatment

 Nomenclature

 Systematic names

 Alkyl chain variations in alcohols

 Simple alcohols

 Higher alcohols

 Etymology

 Physical and chemical properties

 Applications

 Alcoholic beverages

 Antifreeze

 Antiseptics

 Fuels

 Preservative

 Solvents

 Production

 Ziegler and oxo processes

 Hydration reactions

 Biological routes

 Laboratory synthesis

1
 Substitution

 Reduction

 Hydrolysis

 Reactions

 Deprotonation

 Nucleophilic substitution

 Dehydration

 Esterification

 Oxidation

 Serving measures

 Shot sizes

 Standard drinks

 Food energy

 Laws

 Ethanol considered as a drug

 Timeline

 Conclusion

2
 ALCOHOL

The hydroxyl (-OH) functional group with bond angle

In chemistry, an alcohol is any organic compound in which

the hydroxyl functional group(-O H) is bound to

a saturated carbon atom. The term alcohol originally referred to

the primary alcohol ethyl alcohol (ethanol), the predominant

alcohol in alcoholic beverages.

The suffix -ol appears in the IUPAC chemical name of all substances

where the hydroxyl group is the functional group with the highest

priority; in substances where a higher priority group is present the

prefix hydroxy- will appear in the IUPAC name. The suffix -ol in

non-systematic names (such as paracetamol or cholesterol) also

typically indicates that the substance includes a hydroxyl

functional group and, so, can be termed an alcohol. But many

substances, particularly sugars (examples glucose and sucrose)

contain hydroxyl functional groups without using the suffix. An

important class of alcohols are the simpleacyclic alcohols, the

general formula for which is CnH2n+1OH.

3
Occurrence in nature

Alcohols have been found outside the Solar System where they can be

found in low densities in star and planetary-system-forming regions

of space.

Toxicity

Ball-and-stick model of tert-Amyl alcohol, which is 20 times more

intoxicating than ethanol and like all tertiary alcohols, cannot be

metabolised to toxic aldehydes.

Ethanol is thought to cause harm partly as a result of direct

damage to DNA caused by its metabolites.

Most significant of the possible long-term effects of ethanol. In

addition, in pregnant women, it causes fetal alcohol syndrome.

4
Ethanol's toxicity is largely caused by its primary

metabolite, acetaldehyde(systematically ethanal) and secondary

metabolite, acetic acid. All primary alcohols are broken down into

aldehydes then to carboxylic acids whose toxicities are similar to

acetaldehyde and acetic acid. Metabolite toxicity is reduced in rats

fed N-acetylcysteine and thiamine.

Tertiary alcohols cannot be metabolized into aldehydes and as a

result they cause no hangover or toxicity through this mechanism.

Some secondary and tertiary alcohols are less poisonous than

ethanol because the liver is unable to metabolize them into toxic by-

products. This makes them more suitable for recreational and

medicinal use as the chronic harms are

lower. Ethchlorvynol and tert-amyl alcohol are tertiary alcohols

which have seen both medicinal and recreational use.

Isopropyl alcohol is oxidized to form acetone by alcohol

dehydrogenase in the liver but has occasionally been abused

byalcoholics, leading to a range of adverse health effects.

Treatment

An effective treatment to prevent toxicity after methanol or ethylene

glycol ingestion is to administer ethanol. Alcohol dehydrogenase

has a higher affinity for ethanol, thus preventing methanol from

binding and acting as a substrate. Any remaining methanol will

then have time to be excreted through the kidneys.

5
 Nomenclature

Systematic names

IUPAC nomenclature is used in scientific publications and where

precise identification of the substance is important, especially in

cases where the relative complexity of the molecule does not make

such a systematic name unwieldy. In the IUPAC system, in naming

simple alcohols, the name of the alkane chain loses the terminal "e"

and adds "ol", e.g., as in "methanol" and "ethanol". When necessary,

the position of the hydroxyl group is indicated by a number between

the alkane name and the "ol": propan-1-ol for

CH3CH2CH2OH, propan-2-ol for CH3CH(OH)CH3. If a higher priority

group is present (such as an aldehyde, ketone, or carboxylic acid),

then the prefix "hydroxy" is used, e.g., as in 1-hydroxy-2-propanone

(CH3C(O)CH2OH).

Some examples of simple alcohols and how to name them

Common names

In other less formal contexts, an alcohol is often called with the

name of the corresponding alkyl group followed by the word

6
"alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl alcohol may

be n-propyl alcohol or isopropyl alcohol, depending on whether the

hydroxyl group is bonded to the end or middle carbon on the

straight propane chain. As described under systematic naming, if

another group on the molecule takes priority, the alcohol moiety is

often indicated using the "hydroxy-" prefix.

Alcohols are then classified into primary, secondary (sec-, s-), and

tertiary (tert-, t-), based upon the number of carbon atoms

connected to the carbon atom that bears the hydroxyl functional

group. (The respective numeric shorthands 1°, 2°, and 3° are also

sometimes used in informal settings.[citation needed]) The primary alcohols

have general formulas RCH2OH; methanol (CH3OH is the simplest

primary alcohol (R=H), and after it, ethanol (R=CH3). Secondary

alcohols can be referred to with the shorthand RR'CHOH; 2-propanol

is the simplest example (R=R'=CH3). Tertiary alcohols can be referred

to with the shorthand RR'R"COH; tert-butanol (2-methylpropan-2-

ol) is the simplest example (R=R'=R"=CH3). In these shorthands, R, R',

and R" represent substituents, alkyl or other attached, generally

organic groups.

Alkyl chain variations in alcohols

Short-chain alcohols have alkyl chains of 1-3 carbons. Medium-

chain alcohols have alkyl chains of 4-7 carbons. Long-chain

alcohols (also known as fatty alcohols) have alkyl chains of 8-21

carbons, and very long-chain alcohols have alkyl chains of 22

carbons or longer.

7
Simple alcohols

"Simple alcohols" appears to be a completely undefined term.

However, simple alcohols are often referred to by common names

derived by adding the word "alcohol" to the name of the appropriate

alkyl group. For instance, a chain consisting of one carbon (a

methyl group, CH3) with an OH group attached to the carbon is

called "methyl alcohol" while a chain of two carbons (an ethyl

group, CH2CH3) with an OH group connected to the CH2 is called

"ethyl alcohol." For more complex alcohols, the IUPAC nomenclature

must be used.

Simple alcohols, in particular ethanol and methanol,

possess denaturing and inert rendering properties, leading to their

use as anti-microbial agents in medicine, pharmacy, and industry.

Higher alcohols

Encyclopædia Britannica states, "The higher alcohols - those

containing 4 to 10 carbon atoms – are somewhat viscous, or oily,

and they have heavier fruity odours. Some of the highly branched

alcohols and many alcohols containing more than 12 carbon

atoms are solids at room temperature."

Like ethanol, butanol can be produced by fermentation processes.

Saccharomyces yeast are known to produce these higher alcohols at

temperatures above 75 °F (24 °C). The bacterium Clostridium

8
acetobutylicum can feeds on cellulose to produce butanol on an
industrial scale.

Etymology

The word alcohol appears in English as a term for a very fine powder

in the sixteenth century. It was borrowed from French, which took it

from medical Latin.

Ultimately the word is from the Arabic ‫( كحل‬al-kuḥl, "kohl, a powder

used as an eyeliner"). Al- is the Arabic definitive article, equivalent

to the in English; alcohol was originally used for the very fine

powder produced by the sublimation of the natural

mineral stibnite to form antimony sulfide Sb2S3 (hence the essence or

"spirit" of the substance), which was used as anantiseptic, eyeliner,

and cosmetic (see kohl (cosmetics)). Bartholomew Traheron, in his

1543 translation of John of Vigo, introduces the word as a term used

by "barbarous" (Moorish) authors for "fine powder." Vigo wrote: the

Physical and chemical properties

Alcohols have an odor that is often described as “biting” and as

“hanging” in the nasal passages. Ethanol has a slightly sweeter (or

more fruit-like) odor than the other alcohols.

In general, the hydroxyl group makes the alcohol molecule polar.

Those groups can form hydrogen bonds to one another and to other

compounds (except in certain large molecules where the hydroxyl is

protected by steric hindrance of adjacent groups[34]). This hydrogen

bonding means that alcohols can be used as protic solvents. Two

9
opposing solubility trends in alcohols are: the tendency of the polar

OH to promote solubility in water, and the tendency of the carbon

chain to resist it. Thus, methanol, ethanol, and propanol are

miscible in water because the hydroxyl group wins out over the short

carbon chain. Butanol, with a four-carbon chain, is moderately

soluble because of a balance between the two trends. Alcohols of five

or more carbons (pentanol and higher) are effectively insoluble in

water because of the hydrocarbon chain's dominance. All simple

alcohols are miscible in organic solvents.

Because of hydrogen bonding, alcohols tend to have higher boiling

points than comparable hydrocarbons and ethers. The boiling point

of the alcohol ethanol is 78.29 °C, compared to 69 °C for the

hydrocarbon hexane (a common constituent ofgasoline), and

34.6 °C for diethyl ether.

Alcohols, like water, can show either acidic or basic properties at the

-OH group. With a pKa of around 16-19, they are, in general, slightly

Alcohols can also undergo oxidation to give aldehydes, ketones,

or carboxylic acids, or they can be dehydrated to alkenes. They can

react to form ester compounds, and they can (if activated first)

undergo nucleophilic substitution reactions. The lone pairs of

electrons on the oxygen of the hydroxyl group also makes alcohols

10
nucleophiles. For more details, see thereactions of alcohols section

below.

As one moves from primary to secondary to tertiary alcohols with the

same backbone, the hydrogen bond strength, the boiling point, and

the acidity typically decrease.

Applications

Total recorded alcohol per capita consumption (15+), in litres of

pure alcohol

Alcohol has a long history of several uses worldwide. It is found in

alcoholic beverages sold to adults, as fuel, and also has many

scientific, medical, and industrial uses. The term alcohol-free is

often used to describe a product that does not contain alcohol. Some

consumers of some commercially prepared products may view

alcohol as an undesirable ingredient, particularly in products

intended for children.

Alcoholic beverages

Alcoholic beverages, typically containing 3–40% ethanol by volume,

have been produced and consumed by humans since pre-historic

times. Other alcohols such as 2-methyl-2-butanol (found in beer)

and γ-hydroxybutyric acid are also consumed by humans for their

psychoactive effects.

11
Antifreeze

A 50% v/v (by volume) solution of ethylene glycol in water is

commonly used as an antifreeze.

Antiseptics

Ethanol can be used as an antiseptic to disinfect the skin before

injections are given, often along with iodine. Ethanol-

basedsoaps are becoming common in restaurants and are

convenient because they do not require drying due to the volatility

of the compound. Alcohol based gels have become common as hand

sanitizers.

Fuels

Some alcohols, mainly ethanol and methanol, can be used as

an alcohol fuel. Fuel performance can be increased in forced

induction internal combustion engines by injecting alcohol into the

air intake after the turbocharger or supercharger has pressurized

the air. This cools the pressurized air, providing a denser air

charge, which allows for more fuel, and therefore more power.

Preservative

Alcohol is often used as a preservative for specimens in the fields of

science and medicine.

Solvents

Hydroxyl groups (-OH), found in alcohols, are polar and

therefore hydrophilic (water loving) but their carbon chain portion

isnon-polar which make them hydrophobic. The molecule

12
increasingly becomes overall more nonpolar and therefore less

soluble in the polar water as the carbon chain becomes

Production

Ziegler and oxo processes

In the Ziegler process, linear alcohols are produced from ethylene

and triethylaluminium followed by oxidation and hydrolysis. An

idealized synthesis of 1-octanol is shown:

Al(C2H5)3 + 9 C2H4 → Al(C8H17)3

Al(C8H17)3 + 3 O + 3 H2O → 3 HOC8H17 + Al(OH)3

The process generates a range of alcohols that are separated

by distillation.

Many higher alcohols are produced by hydroformylation of alkenes

followed by hydrogenation. When applied to a terminal alkene, as is

common, one typically obtains a linear alcohol:[37]

RCH=CH2 + H2 + CO → RCH2CH2CHO

RCH2CH2CHO + 3 H2 → RCH2CH2CH2OH

Such processes give fatty alcohols, which are useful for detergents.

Hydration reactions

Low molecular weight alcohols of industrial importance are

produced by the addition of water to alkenes. Ethanol, isopropanol,

2-butanol, and tert-butanol are produced by this general method.

Two implementations are employed, the direct and indirect

methods. The direct method avoids the formation of stable

13
intermediates, typically using acid catalysts. In the indirect

method, the alkene is converted to the sulfate ester, which is

subsequently hydrolyzed. The

direct hydrationusing ethylene (ethylene hydration)[38] or other

alkenes from cracking of fractions of distilled crude oil.

Hydration is also used industrially to produce the diol ethylene

glycol from ethylene oxide.

Biological routes

Ethanol is obtained by fermentation using glucose produced from

sugar from the hydrolysis of starch, in the presence of yeast and

temperature of less than 37 °C to produce ethanol. For instance, such

a process might proceed by the conversion of sucrose by the

enzyme inverts into glucose and fructose, then the conversion

of glucose by the enzymezymase into ethanol (and carbon dioxide).

Several of the benign bacteria in the intestine use fermentation as

a form of anaerobic metabolism. This metabolic reaction

produces ethanol as a waste product, just like aerobic

respiration produces carbon dioxide and water. Thus, human

bodies contain some quantity of alcohol endogenously produced by

these bacteria. In rare cases, this can be sufficient to cause "auto-

brewery syndrome" in which intoxicating quantities of alcohol are

produced.

Laboratory synthesis

14
Several methods exist for the preparation of alcohols in the

laboratory.

Substitution

Primary alkyl halides react with aqueous NaOH or KOH mainly to

primary alcohols in nucleophilic aliphatic substitution. (Secondary

and especially tertiary alkyl halides will give the elimination

(alkene) product instead). Grignard reagents react

with carbonyl groups to secondary and tertiary alcohols. Related

reactions are the Barbier reaction and the Nozaki-Hiyama

reaction.

Reduction

Aldehydes or ketones are reduced with sodium

borohydride or lithium aluminium hydride (after an acidic

workup). Another reduction by aluminiumisopropylates is

the Meerwein-Ponndorf-Verley reduction. Noyori asymmetric

hydrogenation is the asymmetric reduction of β-keto-esters.

Hydrolysis

Alkenes engage in an acid catalysed hydration reaction using

concentrated sulfuric acid as a catalyst that gives usually

secondary or tertiary alcohols. The hydroboration-

oxidation and oxymercuration-reduction of alkenes are more

reliable in organic synthesis. Alkenes react with NBS and water

15
in halohydrin formation reaction. Amines can be converted

todiazonium salts, which are then hydrolyzed.

The formation of a secondary alcohol via reduction and hydration

is shown:

Reactions

Deprotonation

Alcohols can behave as weak acids, undergoing deprotonation. The

deprotonation reaction to produce an alkoxide salt is performed

either with a strong base such as sodium hydride or n-

butyllithium or with sodium or potassium metal.

2 R-OH + 2 NaH → 2 R-O-Na+ + 2H2↑

2 R-OH + 2 Na → 2 R-O−Na+ + H2

2 CH3CH2-OH + 2 Na → 2 CH3-CH2-O-Na+ + H2↑

Water is similar in pKa to many alcohols, so with sodium

hydroxide there is an equilibrium set-up, which usually lies to the

left:

R-OH + NaOH ⇌ R-O-Na+ + H2O (equilibrium to the left)

16
It should be noted, however, that the bases used to deprotonate

alcohols are strong themselves. The bases used and the alkoxides

created are both highly moisture-sensitive chemical reagents.

The acidity of alcohols is also affected by the overall stability of the

alkoxide ion. Electron-withdrawing groups attached to the carbon

containing the hydroxyl group will serve to stabilize the alkoxide

when formed, thus resulting in greater acidity. On the other hand,

the presence of electron-donating group will result in a less stable

alkoxide ion formed. This will result in a scenario whereby the

unstable alkoxide ion formed will tend to accept a proton to reform

the original alcohol.

With alkyl halides alkoxides give rise to ethers in the Williamson

ether synthesis.

Nucleophilic substitution

The OH group is not a good leaving group in nucleophilic

substitution reactions, so neutral alcohols do not react in such

reactions. However, if the oxygen is first protonated to give R−OH2+,

the leaving group (water) is much more stable, and the nucleophilic

substitution can take place. For instance, tertiary alcohols react

with hydrochloric acid to produce tertiary alkyl halides, where

the hydroxyl group is replaced by a chlorine atom by unimolecular

nucleophilic substitution. If primary or secondary alcohols are to be

reacted with hydrochloric acid, an activator such as zinc

chloride is needed. In alternative fashion, the conversion may be

performed directly using thionyl chloride.

17
Alcohols may, likewise, be converted to alkyl bromides

using hydrobromic acid or phosphorus tribromide, for example:

3 R-OH + PBr3 → 3 RBr + H3PO3

Dehydration

Alcohols are themselves nucleophilic, so R−OH2+ can react with ROH

to produce ethers and water in a dehydration reaction, although

this reaction is rarely used except in the manufacture of diethyl

ether.

This is a diagram of acid catalysed dehydration of ethanol to

produce ethene:

A more controlled elimination reaction is the Chugaev

elimination with carbon disulfide and iodomethane.

Esterification

To form an ester from an alcohol and a carboxylic acid the

reaction, known as Fischer esterification, is usually performed

atreflux with a catalyst of concentrated sulfuric acid:

R-OH + R'-COOH → R'-COOR + H2O

In order to drive the equilibrium to the right and produce a

good yield of ester, water is usually removed, either by an excess of

H2SO4 or by using a Dean-Stark apparatus. Esters may also be

18
prepared by reaction of the alcohol with an acid chloride in the

presence of a base such as pyridine.

Other types of ester are prepared in a similar manner – for

example, tosyl (tosylate) esters are made by reaction of the alcohol

with p-toluenesulfonyl chloride in pyridine.

Oxidation

Primary alcohols (R-CH2-OH) can be oxidized either

to aldehydes (R-CHO) or to carboxylic acids (R-CO2H), while the

oxidation of secondary alcohols (R1R2CH-OH) normally terminates

at the ketone (R1R2C=O) stage. Tertiary alcohols (R1R2R3C-OH) are

resistant to oxidation.

The direct oxidation of primary alcohols to carboxylic

acids normally proceeds via the corresponding aldehyde, which is

transformed via an aldehyde hydrate (R-CH(OH)2) by reaction with

water before it can be further oxidized to the carboxylic acid.

Mechanism of oxidation of primary alcohols to carboxylic acids via

aldehydes and aldehyde hydrates

Reagents useful for the transformation of primary alcohols to

aldehydes are normally also suitable for the oxidation of secondary

alcohols to ketones. These include Collins reagent and Dess-Martin

periodinane. The direct oxidation of primary alcohols to carboxylic

19
acids can be carried out using potassium permanganate or

the Jones reagent.

Serving measures

Shot sizes

Shot sizes varies significantly from country to country. In the United

Kingdom, serving size in licensed premises is regulated under

the Weights and Measures Act (1985). A single serving size of spirits

(gin, whisky, rum, and vodka) are sold in 25 ml or 35 ml quantities

or multiples thereof.[19] Beer is typically served in pints (568 ml), but

is also served in half-pints or third-pints. In Israel, a single serving

size of spirits is about twice as much, 50 or 60 mL.

The shape of a glass can have a significant effect on how much one

pours. A Cornell University study of students and bartenders'

pouring showed both groups pour more into short, wide glasses than

into tall, slender glasses.[20] Aiming to pour one shot of alcohol (1.5

ounces or 44.3 ml), students on average poured 45.5 ml & 59.6 ml

(30% more) respectively into the tall and short glasses. The

bartenders scored similarly, on average pouring 20.5% more into

the short glasses. More experienced bartenders were more accurate,

pouring 10.3% less alcohol than less experienced bartenders.

Practice reduced the tendency of both groups to over pour for tall,

slender glasses but not for short, wide glasses. These misperceptions

are attributed to two perceptual biases: (1) Estimating that tall,

slender glasses have more volume than shorter, wider glasses; and

20
 Standard drinks

Standard Drink

A standard drink is a notional drink that contains a specified

amount of pure alcohol. The standard drink is used in many

countries to quantify alcohol intake. It is usually expressed as a

measure of beer, wine, or spirits. One standard drink always

contains the same amount of alcohol regardless of serving size or

the type of alcoholic beverage.

The standard drink varies significantly from country to country. For

example, it is 7.62 ml (6 grams) of alcohol in Austria, but

in Japan it is 25 ml (19.75 grams).

In the United Kingdom, there is a system of units of alcohol which

serves as a guideline for alcohol consumption. A single unit of

alcohol is defined as 10 ml. The number of units present in a typical

drink is sometimes printed on bottles. The system is intended as an

aid to people who are regulating the amount of alcohol they drink;

it is not used to determine serving sizes.

21
In the United States, the standard drink contains 0.6 US fluid

ounces (18 ml) of alcohol. This is approximately the amount of

alcohol in a 12-US-fluid-ounce (350 ml) glass of beer, a 5-US-fluid-

ounce (150 ml) glass of wine, or a 1.5-US-fluid-ounce (44 ml) glass

of a 40% ABV (80 US proof) spirit.

Food energy

Alcoholic beverages are a source of food energy. The USDA uses a

figure of 6.93 kcal per gram of alcohol (5.47 kcal perml) for

calculating food energy.[21] In addition to alcohol, many alcoholic

beverages contain carbohydrates. For example, beer usually

contains 10–15 g of carbohydrates (40–60 kcal) per 12 US fluid

ounces (350 ml) which may contribute to an increase in body

weight and beer belly.

However, aside from the direct effect of its caloric content, alcohol is

known to potentiate the insulin response of the human body

to glucose, which, in essence, "instructs" the body to convert

consumed carbohydrates into fat and to suppress carbohydrate and

fat oxidation.

Laws

Alcohol laws regulate the manufacture, sale, and consumption of

alcoholic beverages. Such laws seek to reduce the health and social

effects of their consumption.

In particular, alcohol laws specify the legal drinking age, which

usually varies between 16 and 25 years, sometimes depending upon

22
the type of beverage. Some countries do not have a legal drinking or

purchasing age, but most set the minimum age at 18 years.[1] Such

laws may take the form of permitting distribution only to licensed

stores or monopoly stores, and they are often combined with

taxation.

In some jurisdictions, alcoholic beverages are totally prohibited for

reasons of religion (e.g., Islamic countries with sharia law) or for

reasons of public health and morals (e.g., Prohibition in the United

States from 1920 to 1933). In jurisdictions which enforce sharia law,

the consumption of alcoholic beverages is a legal offense, although

such laws may exempt non-Muslims.

Ethanol considered as a drug

Ethanol (commonly called alcohol) is a psychoactive drug that is

found in alcoholic beverages. Ethanol is one of the most commonly

abused drugs (Meropol, 1996)[28] and is often used for self-

medication and as recreational drug.

23
 Timeline

Members of a German Student Corps(Duchy of Brunswick) shown

drinking in a picture from 1837.

 10,000 BC: Discovery of late Stone Age jugs suggest that

intentionally fermented beverages existed at least as early as

the Neolithic period (cir. 10,000 BC).

 7000–5600 BC: Examination and analysis of

ancient pottery jars from the neolithic village of Jiahu in

the Henan province of northern China revealed residue left

behind by the alcoholic beverages they had once contained.

According to a study published in the Proceedings of the

National Academy of Sciences, chemical analysis of the residue

confirmed that a fermented drink made of grape and

hawthorn fruit wine, honey mead and rice beer was being

produced in 7000–5600 BC (McGovern et al., 2005; McGovern

2009). The results of this analysis were published in December

2004.

24
 Conclusion

Alcohol is not an ordinary commodity. While it carries connotations

of pleasure and sociability in the minds of many, harmful

consequences of its use are diverse and widespread

From a global perspective, in order to reduce the harm caused

by alcohol, policies need to take into account specific situations in

different societies. Average volumes consumed and patterns of

drinking are two dimensions of alcohol consumption that need to

be considered in efforts to reduce the burden of alcohol-related

problems. Avoiding the combination of drinking and driving is an

example of measures that can reduce the health burden of alcohol.

Worlwide, alcohol takes an enormous toll on lives and communities,

especially in developing countries and its contribution to the overall

burden of disease is expected to increase in the future. Particularly

worrying trends are the increases in the average amount of alcohol

consumed per person in countries such as China and India and the

more harmful and risky drinking patterns among young people.

National monitoring systems need to be developed to keep track

of alcohol consumption and its consequences, and to raise

awareness amongst the public and policy-makers. It is up to both

governments and concerned citizens to encourage debate and

formulate effective public health policies that minimize the harm

caused by alcohol.

25