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ORGANIC CHEMISTRY-2

PREPARATION OF THE ALCOHOL.

Ethanol is commercially produced using a process called fermentation. Many other alcohols can be made this way, but are more likely to be produced by synthetic routes - from natural gas, oil or coal.

Fermentation is the process in which yeast breaks down sugar into alcohol and carbon dioxide. Yeast is tiny. The process does not need oxygen, hence it is the form of anaerobic respiration.

These are two types of fermentation

a) Alcoholic fermentation – producing alcohol

b) Lactic acid fermentation – producing lactic acid

The word equation for this process is:

Glucose + yeast → alcohol + carbon dioxide

Carbon dioxide gas bubbles out of the fermenting solution into the air leaving a mixture of ethanol and water. It's important that no air is present or the yeast will produce ethanoic acid - the chemical found in vinegar.

Beer and lagers Barley, hops, water and live yeast produce beers and lagers. The sugar in the mix comes from the spouting barley. Bitter, stout and ale use top-fermenting yeast, while lager uses a variety that sinks to the bottom.

Wine In wine making the sugars come from the flesh of the crushed grapes. The type of wine produced depends on the type of grape used in the process.

Spirits and distillation

Yeast cannot survive in high levels of alcohol, so to create stronger spirits an additional process, distillation, is required. Fermented drinks are distilled to create vodka, rum and other spirits. Distillation relies on ethanol having a lower boiling point than water. When the fermented drink is heated the ethanol vaporizes at 78.5 degrees and the water is left behind (water boils or vaporizes at 100 degrees). The ethanol gas is caught and cooled so it condenses into a stronger concentration of ethanol liquid.

Alcohol can be prepared locally or in the industries

1. Local preparation of the alcohol; raw material – sugar beet, cereals such as (cassava, millet, maize)

b) Industrial preparation of the alcohol; Raw material – maltose sugar – C 12 H 22 O 11

The enzyme known as the diastase help to covert the starch to maltose; normally the starch containing food are crushed then treated with the steam to extract starch from them. The malt from Barley added in order to convert the starch to maltose, the mixture allowed to stay for about one hour also yeast can be added, and the yeast contains two enzymes maltose and zymase.

and the yeast contains two enzymes maltose and zymase. Definition: Fractional distillation – is the process

Definition: Fractional distillation – is the process used to separate the components of the homogeneous mixtures which differ in the boiling points 9BP) consider the diagram below

Where A – Stand for ethanol – C 2 H 5 OH B – Cold

Where

A – Stand for ethanol – C 2 H 5 OH

B – Cold water to distillate ethan ol vapors to liquid

C – Ethanol (78 0 c) and water (10 0 0 c)

D – Ethanol vapour

E – Ethanol drops

F – Thermometer record temper ature

G – Stand and clump

H – Cork

I – Condenser

K- Round bottom ed flask

A 1 - Ethanol(C 2H5OH)

A 0 -Beaker(Conta iner)

Note

1. The mixture boiled until temperature reach about 80 – 85 0 c then stopped at this point all ethanol become extracted from the mother solution

2. The yeast cells are killed by the high temperature

3. The yeast contains two enzymes known as Maltose, and Zymase

4. Alcohol can also prepared from the sugar cane

E.g. sugar cane + water yeast → Glucose + Fructose

Sucrose + water → Glucose + Fructose

C 12 H 22 O 11 + H 2 O → CH 12 O 6 + C 6 H 2 O 6

The invertase enzymes connect sucrose to glucose and fructose

PROPERTIES OF THE ALCOHOL

The following are the properties of the Alcohol

1. It is colorless and has odour taste

2. It is soluble in water and can from the homogeneous mixture water

3. It boils at 78 o c

4. Purely ethanol is non – electrolyte

REACTION IN ALCOHOL

They includes

1. Reaction with Carboxylic Acid

IN ALCOHOL They includes 1. Reaction with Carboxylic Acid  Alcohol reacts with carboxylic acid to

Alcohol reacts with carboxylic acid to form "Ester" and water, hence reaction called Esterification reaction

Example

2. Reaction with Electropositive metals E.g. Alcohol + Electropositive metals Examples salt + hydrogen Ethanol

2. Reaction with Electropositive metals

E.g. Alcohol + Electropositive metals

Examples

salt + hydrogen

Ethanol + sodium → sodiumethoxide + hydrogen

C 2 H 5 OH + Na → C 2 H 5 ONa + H 2 O

Ethanol + Potassium → potassiumethoxide + hydrogen

C 2 H 5 OH + K → C 2 H 5 OK + H 2

3. Oxidizing agent reaction e.g. potassium permanganate – KmnO 4 or (O)

E.g. Alcohol + oxidizing agent → Carboxylic acid

Example

Ethanol + (O) → Ethanoic acid

C 2 H 5 OH + (O) → CH 3 COOH

4. Reaction with concentrated sulphuric acid Con. H 2 SO 4 at 180 0 c/ 140 0 c

Example

Con. H 2 SO 4 at 180 0 c/ 140 0 c Example In this reaction

In this reaction acid acts or behave as dehydrating since removed water from the Alcohol

5. Reaction with PCl 5 , PCl 3 , SOCl 2 E.g. ROH + PCl

5. Reaction with PCl 5 , PCl 3 , SOCl 2

E.g.

ROH + PCl 5 → RCl + POCl 3 + HCl

C 2 H 5 OH + PCl 5 → C 2 H 5 Cl + pOCl 3 + HCl

ROH + PCl 3 → RCl + H 3 PO 4 + HCl

C 2 H 5 OH +PCl 3 → C 2 H 5 Cl + H 3 PO 4 + HCl

ROH + SOCl 2 → RCl + SO 4 + HCl

C 2 H 5 OH + SOCl 2 → C 2 H 5 Cl + SO 2 + HCl

Where

PCl 5 – phosphorus pentachloride, PCl3 – phosphorus trichloride

SOCl 2 – sulphuric trichloride or vinyl chloride

Note

SOCl 2 – sulphuric trichloride or vinyl chloride Note COMMERCIAL USES OF ETHANOL – C 2

COMMERCIAL USES OF ETHANOL – C 2 H 5 OH

(sterilization). E.g. Methanol (5%) extracted by the dry distillation of the wood mixed with 95%- ethanol then we obtain methylated spirit which is coloured before being sold to the public this is to avoid the ethanol from being consumed as the drink.

2. They can be used for

Preservation of the specimen and food

Fuel and light

Varnishes, polishes, paint making and removing

Temporary solvent in the manufacture of the soap, medicine, also to precipitate the chemicals from their aqueous solutions

Raw materials for the manufacture of the chemical such as trichloromethane and ethane

3. Manufacture of the Alcoholic drinks egg beer contains 2 – 6% ethanol, made by

fermenting mash barley. Wines are made grapes, and yeast for the fermentation grows on

the skin of the grapes. Wines contains 10% ethanol

Note: sugar beet molasses – Are the remains of sugarcane

HARMFUL EFFECT OF ALCOHOL

Alcohols have much harmful effects to the body, if taken as a drink. However, the effect of a given amount of ethanol depends on the rate of drinking, the size of the drinker, the alcoholic content of the drink, health and diet of the drinker and other factors.

The noticeable harmful effects of alcohols including:

1)

abstract reasoning and destroys liver cells.

Heavy drinking of alcohol causes shrinkage of the brain cells, reduces power of

2)

Heavy drinking can cause cancer of the liver, stomach and gullet.

3)

Heavy drinking can upset digestion and reduce blood cell formation thus causing

anaemia.

4)

Some of car accidents by drivers is due to heavy alcohol drinking. Don’t drink and

drive.

5)

Alcohol drinking can be one of the sources of family conflicts, misunderstandings,

misuse of money and even divorce.

6)

permanent blindness or death.

Methanol(methyl alcohol) is quite toxic. Ingestion of as little as 30ml can cause

CARBOXYLIC ACID

A carboxylic acid is an organic compound that contains a carboxyl group (C(O)OH). The general

formula of a carboxylic acid is R-C(O)OH with R referring to the rest of the (possibly quite large) molecule. Carboxylic acids occur widely, and include the amino acids and acetic acid (active ingredient in vinegar).

The general formula

acid (active ingredient in vinegar). The general formula Where R = CH 3 or C 2

Where

R = CH 3 or C 2 H 5 = alky group

Example

R

= CH 3 = CH 3 COOH

R

= C 2 H 5 = C 2 H 5 COOH

Note: Function Group – COOH of carboxylic acid can’t move from the first or last carbon ( c ) atom, this mean functional group is fixed but that of alcohol can move

NO OF

   

CARBON

NAME OF ACID

MOLECULAR FORMULA

n

= 1

Methanoic (formic)

CH 2

O

n

= 2

Ethanoic acid

C

2

H

4 O

2

 

n

= 3

Propanoic acid

C

3

H

6 O

2

n

= 4

Botanic acid

C

4

H

8 O

2

n

= 5

Pentanoic acid

C

5

H

10

O

2

n

= 6

Hexanoic acid

C

6

H

12

O

2

n

= 7

Heptanoic acid

C

7

H

14

O

2

n

= 8

Octanoic acid

C

8

H

16

O

2

n

= 9

Nonanoic acid

C

9 H 18 O 2

n

= 10

Decanoic acid

C

10 H 20 O 2

CARBOXYLIC ACID

Carboxylic acids are organic aci ds that are characterized by R-COOH group. Th e R is an alkyl group. The functional group is

group. Th e R is an alkyl group. The functional group is Organic acids have the

Organic acids have the general f ormula

Where n = 1, 2, 3,

Organic acids have the general f ormula Where n = 1, 2, 3, From the general
Organic acids have the general f ormula Where n = 1, 2, 3, From the general

From the general formula the fir st five members of homologous series are show n in table below.

Ho mologous series of carboxylic acid.

n in table below. Ho mologous series of carboxylic acid. NB It seems that homologous se

NB It seems that homologous se ries of carboxylic acid that the carboxylic acid c an be

represented by using the general molecular formula of

an be represented by using the general molecular formula of . where n = number of

.

where n = number of carbon atoms in the compound.

STRUCTURAL FORMULA OF

Condensed and open structural f ormula of carboxylic acid.

SOME CARBOXYLIC ACIDS

NOMENCLATURE OF CAR BOXYLIC ACIDS In naming carboxylic acids, all r ules of naming alkenes

NOMENCLATURE OF CAR BOXYLIC ACIDS

In naming carboxylic acids, all r ules of naming alkenes are used except the mod ifications that follows:

(i) The suffix ‘e” of alkanes is re placed by suffix ‘oic” of carboxylic acid.

eg; Alkane

Carboxylic acid

1. Methane

-Methanoic acid

2. Ethane

-Ethanoic acid

3. Propane

-Propanoic acid

(ii) The longest chain of carbox ylic acid must includes the carboxylic group

must includes the carboxylic gro up

eg: (i) CH 3 CH 2 CH 2 CH 2 COOH – Pentanoic acid (ii)CH

eg: (i) CH 3 CH 2 CH 2 CH 2 COOH – Pentanoic acid

(ii)CH 3 CH 2 COOH – Propanoic acid

(iii) If the substituent groups are attached to the parental chain of the Carboxyli c acid, their

position must be indicated. Num bering starts the side where by carboxylic grou p (COOH) is

early attached.

eg:

where by carboxylic grou p (COOH) is early attached. eg: Trichlonobutanoic acid 4, 4,4 - R-5.7.1.2

Trichlonobutanoic acid

4, 4,4 -

R-5.7.1.2 Substituted carboxyl ic acids

Hydroxy, alkoxy, and oxo acids. Some trivial names for hydroxyl and alkoxy ac ids are retained. The names of carboxylic acids c ontaining an aldehydic group attached to, or a k etonic group

contained in the principal chain

the corresponding simple carbox ylic acids by adding prefixes such as "oxo-", "d ioxo-", etc.,

denoting =O substituents, or "for myl-", demoting a -CHO substituent.

or parent ring system, are generally derived from

the names of

Example

or "for myl-", demoting a -CHO substituent. or parent ring system, are generally derived from the

The carboxylic acid also has common which people they know due to daily uses of such carboxylic acid

people they know due to daily uses of such carboxylic acid Give the IUPAC names of

Give the IUPAC names of the following compounds

acid Give the IUPAC names of the following compounds IUPAC name: 2, 3 – dibromobutanoic acid

IUPAC name: 2, 3 – dibromobutanoic acid

the following compounds IUPAC name: 2, 3 – dibromobutanoic acid IUPAC name 2 – Chloro, 4,

IUPAC name

2 – Chloro, 4, 5 – dimethylhexanoic acid

iii)

Name

iii) Name 2,2 – dimethylpropanoic acid PROPERTIES OF THE CARBOXYLIC ACID  They are Acidic in

2,2 – dimethylpropanoic acid

PROPERTIES OF THE CARBOXYLIC ACID

They are Acidic in nature so they can react with base then form salt and water

They have carboxylic group as their functional group – COOH

They end up with suffix – "oic"

E.g. Methanoic, Ethanoic

Where

n

= 0… methanoic

n

= 1… ethanoic

n

= 3, 4, 5, 6, 7….10

C

n H 2 nO 2 where n = 1, 2, 3, 4,

REACTION OF CARBOXYLIC ACID – C00H

Carboxylic acid are acidic in nature so they can react with base then form salt and water as other acid (mineral acid)

1. CARBOXYLIC ACID AND BASE (Alkali)

E.g. Acid + base → salt + water

Example

Ethanoic + sodium → sodium + water

Acid

hydroxide →

Ethanoate

CH 3 COOH + NaOH → CH 3 COOHNa + H 2 O

Acetic acid + sodium hydroxide → Sodium Acetate

+ Water

CH 3 COOH + NaOH

→ CH 3 COONa + H2O

Formic Acid + potassium hydroxide

→ Potassium methanoate +

H 2

HCOH + KOH

HCOOK +

water

2. CARBOXYLIC ACID AND METAL (K, Na)

Acid + metal

Example

Acetic Acid + sodium

→ Salt + hydrogen

→ Sodium Acetate + Hydrogen

CH 3 COOH + Na

→ CH 3 COOHNa + H 2

CH 3 COOH + K

CH 3 COOK + H 2

ESTERIFICATION AND NEUTRALIZATION

ESTERIFICATION – Is the reaction between the Alcohol and carboxylic acid under control of concentrated sulphuric acid (H 2 SO 4 ) and heat (Δ)

sulphuric acid (H 2 SO 4 ) and heat (Δ) Acid provide – H- which shift

Acid provide – H- which shift equilibrium position than ester produced

CONDITION FOR ESTERIFICATION

They include

1.

Concentrated sulphuric acid (H 2 SO 4 ) as catalyst. The concentrated sulphuric acid is used as the catalyst to speed up the rate of the chemical reaction.

2. Heat.

PRODUCTS OF ESTERIFICATION

They include

1. Ester

2. water

ESTER – Are the organic compounds with the smell (sweet smell) like fruits and have structure

Example

smell (sweet smell) like fruits and have structure Example NEUTRALIZATION This is the reaction between acid

NEUTRALIZATION

This is the reaction between acid and base (Alkali) to form salt and water

Acid + Base → salt + water

Esterification and neutralization have differences as shown below.

DIFFERENCE BETWEEN ESTERIFICATION AND NEUTRALIZATION

 

ESTERIFICATION

 

NEUTRALIZATION

a)

Is the reaction between carboxylic acid to form salt and water

a)

Is the reaction between acid and base Alcohol and form Ester and water

b)

Is reversible reaction

b)

Is not reversible (Irreversible)

c

Produce "Ester"

 

Produce "salt"

d)

Catalyst used e.g. Acid

d)

catalyst is not used

e)

Produces covalent compound

e)

Produces the Ionic compound

DIFFERENCES BETWEEN ALCOHOL AND CARBOXYLIC ACID

ALCOHOL – OH

Are organic compound with hydroxyl group as functional group e.g. R – OH

Functional group not fixed

as functional group e.g. R – OH Functional group not fixed CARBOXYLIC ACID – COOH Are

CARBOXYLIC ACID – COOH

Are organic compound with carboxylic as group – COOH as functional group R – COOH

Functional group is fixed

– COOH Are organic compound with carboxylic as group – COOH as functional group R –

SAPONIFICATIONS

Saponification is a process that produces soap, usually from fats and lye. It involves a reaction between a base, usually sodium hydroxide (caustic soda), and an ester group on a compound. Triglycerides are an example, which is an ester of a fatty acid. The triglycerides are hydrolyzed to form the sodium salt of a carboxylate. In addition to soap, such traditional saponification processes produce glycerol. "Saponifiable substances" are those that can be converted into soap

substances" are those that can be converted into soap APPLICATION OF THE SAPONIFICATION The knowledge of

APPLICATION OF THE SAPONIFICATION

The knowledge of the saponification is applied in the industries to manufacture soap , Ester such as oil is mixed with the base then salt hence heated (boiled), then soap particles precipitates to form the down ward (boiled), then soap particles.