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STEM Chemistry Marathon

Carbon Chemistry



Essential Question:
What do detergents, proteins, hormones, plastics,
most of food, dyes and pigments, soaps, fertilizers,,
insecticides, smells, tastes, addictive substances,
genetics, bitumen(road surface), perfumes, fuels,
cosmetics, tires, drugs, liquors, anesthetics,
preservatives, beer, win, and digestive enzymes,
nicotine, fibers,…etc. have in common?

Distinguish between organic and inorganic compounds
Differentiate between molecular and structural formulas
Using IUPAC nomenclature
Experimentally determine the carbon and hydrogen in organic
Identify aromatic compounds

1. Isomers (geometric and optical)
• 2. Simple preparation of methane (dry distillation of sodium
• 3. Reactions of hydrocarbons:
o a. combustion in limited and excess amount of oxygen for
o b. halogenation of alkane and alkene by free radical
mechanism (Methane and propane)
o c. catalytic hydration of alkene

o d. addition of HX (alkene only)
o e. polymerization of ethene
o f. catalytic hydration of alkyne
o g. polymerization- trimerization, aromaticity, and
benzene structure
o h. preparation of aromatic benzene (from acetylene –
• 4. Reactions of Benzene
o a. mono substituted benzene
o b. di-substituted benzene
• 5. Distinguish practically between Ethane, Ethene and

Importance of carbon in living organism

• 25 elements make up all living things
• About 97% of your body’s mass is made of just 4
elements: oxygen, carbon, hydrogen, & nitrogen
• If you take away the water, the rest of the human body
is 53% carbon, because of its ability to bond with
other atoms
• Silicon is similar to carbon-tetravalent-. Why are
there no life forms based on silicon like carbon?
Because silicon-silicon covalent bond is not strong
enough for it to form long stable chains. So, it can not
form molecules of the complexity needed to make up
cells like carbon can!




Brezelius considered that organic compounds are formed by vital processes that are found in living cells of the body and it is impossible to be synthesized in the lab. . 2) Inorganic Compounds: They are the compounds that originate from mineral sources in Earth. Vital force theory ■ The scientist Brezelius divided all the compounds into two categories: 1) Organic compounds: They are the compounds that are extracted from animal or plant origin.

. This is because most of organic compounds which were prepared in laboratories are not formed in living organisms.The destroy of the vital force theory ■ In 1828 the German scientist ‘Wöhler’ destroyed the vital force theory when he prepared organic compound (Urea) by heating an aqueous solution of two inorganic compounds (silver cyanate and ammonium chloride) ■ The organic materials become known according to their structure not according to their sources.

homocyclic or heterocyclic. branched chains. either straight chains. Carbon atoms can join together with different methods. What are the reasons of the abundance of organic compounds? ■ The abundance of organic compounds is due to Carbon is tetravalent element can bind with 4 bonds 1.carbon combines together or with others elements (H – N – O – S …) by different kinds of bond forming endless chains. 2. .

Comparison between the organic and inorganic compounds .









1.The Saturated aliphatic acyclic Hydrocarbons (Alkanes) They have general molecular formula CnH2n+2 .





-yl R .

location. . • The prefix tells us the identity. and number of substituents attached to the carbon chain. Nomenclature of Alkanes The parent name indicates the number of carbons in the longest continuous carbon chain in the molecule. • The suffix indicates what functional group is present.

HOW TO Name an Alkane Using the IUPAC System ■ Step 1: Find the parent carbon chain and add the suffix. All of the following representations are equivalent. and name the molecule using the parent name for that number of carbons. add the suffix -ane for an alkane. . • The longest chain may not be written horizontally across the page. • Find the longest continuous carbon chain. Each functional group has its own suffix. Remember that it does not matter if the chain is straight or has bends.

.■ Step 2: Number the atoms in the carbon chain to give the first substituent the lower number. • Name the substituents as alkyl groups. ■ Step 3: Name and number the substituents. and use the numbers from step [2] to designate their location.

For example. • Precede the name of each substituent by the number that indicates its location.for three groups. use prefixes to indicate how many: di. tetra. ■ Step 4: Combine substituent names and numbers + parent + suffix. ignoring any prefixes like di-.■ NOTE → If two or more identical substituents are bonded to the longest chain. triethyl precedes dimethyl because the e of ethyl comes before the m of methyl in the alphabet. and so forth. There must be one number for each substituent. • Precede the name of the parent by the names of the substituents. • Separate numbers by commas and separate numbers from letters by dashes.for two groups. .for four groups. Alphabetize the names of the substituents. tri.

Examples Use punctuation .use commas to separate numbers -hyphens to separate numbers with words. .

3-Trimethylpentane . ■ Example: 2. and the suffix tells us the functional group. number the carbon chain from either end and add the substituents. add enough H’s to give each C four bonds.3. ■ From the parent we know the number of C’s in the longest chain. ■ Then.■ To derive a structure from a name. first look at the end of the name to find the parent name and suffix. the suffix -ane = an alkane. ■ Finally.







The carbon from which the substituent attaches to the main chain is automatically number 1 . ■ (those which are Complex alky groups branched themselves) are named as if they were alkanes. . but the name ends in -yl and is enclosed in parenthesis.


A secondary carbon is one attached to two other carbons. A primary carbon is one that is covalently attached to only one other carbon. A tertiary carbon is attached to three other carbons. . this terminology applies only to sp3 carbons. In the following examples the carbons in question are indicated as dots. since it consists of only one carbon atom. Other types are not defined in this way. ■ Another bit of terminology associated with common names refers to the connectivity of sp3 carbons in alkanes and alkyl groups. Likewise. Secondary. And Tertiary Carbons. This definition implies that methane cannot have any such carbons.Primary.


secondary.How many primary. tertiary carbon atom? .

That is. a trivial name such as white metal can mean various things. neo only are alphabetic order . iso. an accepted part of the nomenclature. A trivial name is not a formal name and is usually a common name eg. Trivial Nomenclature(common) ■ In chemistry. trivial names can be ambiguous or will carry different meanings in different industries or in different geographic regions. neo. Properties such as the molecular structure of a chemical compound are not indicated. ■ Iso. Sec. (For example. the name is not recognized according to the rules of any formal system of chemical nomenclature such as IUPAC inorganic or IUPAC organic nomenclature. tert. in some cases. a trivial name is a nonsystematic name for a chemical substance.) On the other hand. As a result. trivial names are not useful in describing the essential properties of the thing being named. a limited number of trivial chemical names are retained names. And. systematic names can be so convoluted and difficult to parse that their trivial names are preferred.… are trivial naming ■ Generally.


Branching in Alkyl Groups ■ Sec. There will be more than one option! ..WHY? ■ Bec.WHY? ■ Tert.. and butyl only. is used with propyl. is used with butyl and pentyl only.


Collection! .



It can take twists and turns.Take Care!! ■ Make sure you’ve identified the longest continuous carbon chain correctly. Otherwise you might end up with the wrong name. . That’s why one must get used to visualize molecules from different angles and perspectives. The following example illustrates the correct name and an incorrect name based on a horizontal row of carbons. The longest continuous carbon chain doesn’t always have to be a horizontal row of carbons.

Give another name! 5-ISO-BUTYL NONANE .





. and (b) The name has the lowest set of numbers indicating the substituent positions. choose the one that yields the simplest name. That means: (a) The longest continuous carbon chain has the greatest number of substituents.■ If there are several options for choosing the longest continuous carbon chain.





Alkanes: Common Names. . ■ Like alkyl groups. ■ ISOALKANES and ISOALKYL GROUPS: The iso structural unit consists of two methyl groups attached to a common carbon. When this unit is present in an alkane or alky group. Common. but are frequently used for branched alkanes. the common name starts with the prefix iso. alkanes can also have common names. or “trivial” names are rarely used for straight chain alkanes.

■ The same rules apply to isoalkyl groups. .■ When this unit is present in alkanes. The smallest possible isoalkane is then isobutane. but the name starts with the prefix iso. because alkyl groups are always attached to another carbon chain. the molecule is named according to the total number of carbon atoms present. but their names end in -yl. The smallest possible isoalkyl group is the isopropyl group.

. and these two carbons are part of a terminal tert-butyl group. Neo Alkanes ■ The prefix "neo" is used when all but two carbons form a continuous chain.

The most common example for alkanes is Methane (CH4) ■ Methane is the first member. it is found in cool mines that may be exposed to an explosion as a result of its illumination . ■ Preparation of Methane in lab. . it is considered as the simplest organic compound and forms about 90 % of natural gas found under the earth’s crust or accompanied to crude petroleum. BY dry distillation of anhydrous sodium acetate with soda lime is a mixture of NaOH and quick lime CaO Soda lime doesn’t take part in the reaction. Also.It is sometimes called the Gas of swamps because it goes out as bubbles from the bottom of these swamps as a result of decaying of the organic matters.

CaO is a drying agent that helps in reducing the melting points of the reaction mixture and helps in decomposition of sodium acetate. .

Physical properties of alkanes 1) They are all non. C1 to C4 : gases C5 to 17 : liquids as kerosene and gasoline (fuel). 2) Usually. but it may undergo the following reactions: . or by regular oxidizing agents such as potassium permanganate or potassium dichromate . mineral (inorganic) acids at room temp .polar compounds (pure covalent bonds) they are insoluble in water (but soluble in organic solvents) & also have low b.p. Longer chains greater than C17 : solids Chemical properties Alkanes are less reactive than unsaturated compounds because of the strong sigma bond therefore alkanes are not affected by conc.

1-Burning ■ All hydrocarbon burn in excess of O2 produce CO2 and H2O through an exothermic reactions. .


Write the name(s) of each compound. 2-A Halogenation of methane: ■ In indirect sunlight : Alkanes react with halogens by heating to 400ºC or in presence of U.V in a series of reactions called substitution reactions. and their uses? . The product of reaction depends on % (Percentage) of methane and halogen in reaction mixture.

.•The function of ultraviolet light is to provide energy for the homolytic cleavage of halogen (Cl-Cl or Br-Br) to form free radicals •The products are haloalkanes (RX) and hydrogen halides (HX) •The halogenation of alkanes is a free radical substitution reaction •The mono substitution of alkanes refers to the substitution reaction where there is only one hydrogen atom in alkanes substituted by halogen free radical.


Chlorine in the halogenation of propane “Why is bromine more “selective” for the secondary carbon than chlorine?”. 2-B Halogenation of propane: Selectivity in Free Radical Reactions: Bromine vs. .


Uses of halogenated derivatives of alkanes: 1) Chloroform was used for a long time as anesthetic substance but its uses stopped because the inaccurate estimation of the dose for each patient causes the death. Halothane (its common name) is used now as anesthetic substance with safety and its formula 2) The compound 1. .1 trichloro ethane is used in the dry cleaning.1.

3) Freons were used in air conditions and fridges. also as a rushed substance to liquid and perfumes and as a cleaner of electronic sets Freons are considered as halogenated derivative of alkanes as CH4 .tetra flouro methane. non poisonous and non corrosive for metals However Freon’s cause the decay of the ozone layer which protect the earth against harmful effect of ultra violet rays There is an international agreement to prevent their uses starting from 2020. easily to be liquefied. diflouromethane CF2Cl2. . Freons are used by large quantities due to its sheep price. but the famous one is dichloro.

Exercise: Write the skeletal formula of 7-(1.2-diflurobutyl)-5-ethyl tri decane. Is it right? .

3. . 2) Short chain alkenes: as ethene and propene which are used in many chemical industries such as manufacture of polymers . 1) Short chain alkanes: which are used with gasoline to fulfill the permanent world needs.Thermal Catalytic Cracking ■ This process takes place by heating the heavy petroleum products under high pressure and temperature in the presence of a catalyst to produce two kind of products.

2.Home fuel in houses Propane & butane are used as fuel in butagas cylinders. The black carbon is produced by heating methane to 1000˚C in the absence of air. Black carbon is used in the manufacture of car tires. and printing ink .The Economic Importance of Alkanes: 1. black painting.To obtain finely divided carbon. polishes. 3. . (black carbon ). This is a mixture of hydrogen and carbon monoxide which is used as reducing agent or as a flammable fuel.To obtain “water gas”.

. The general form of Cycloalkanes is CnH2n which is the same as the molecular formula of aliphatic alkenes. So we have to differentiate between them on writing their structural formula. Saturated cyclic hydrocarbons (Cycloalkanes) ■ Hydrocarbons which contain three or more carbon atoms may found in cyclic structure.

for example. Therefore . They are very active compared with linear alkanes. These small angles lead to weak overlap between the atomic orbitals. so the overlap between the atomic orbitals becomes more strong therefore a strong sigma bonds are formed. . Cyclopentane and cyclohexane are stable because the angles between the bonds near 109˚.■ Nomenclature of cyclic alkanes is similar to open chain alkane but we put the prefix “cyclo” in case of cyclic alkanes. ■ It is observed that the angles between the bonds in cyclopropane equal 60˚ while they are 90˚ in cyclobutane. while normal propane ( linear propane ) is less active. cyclopropane forms with air an extremely burning mixture . They are less than 109 ˚ which is found in open chain alkanes.the combination between carbon atoms is very weak.

Alkenes (olefins) ■ Unsaturated hydrocarbons that contains double bonds.the longest continuous carbon chain + (ene) . proceeding by the number of the carbon atom nearest to the double bond. 2.Numbering starts from the nearest side to the double bond . ■ Nomenclature of alkenes: 1.

the acidic remains removed by NaOH .preparation of ethylene from alcohol by dehydration ■ Ethene can be prepared by removing water (dehydration) from ethyl alcohol by using hot concentrated (H2SO4) at 180˚C or aluminum ■ Before collecting the gas.


.■ This reaction takes place in two steps: 1.Ethyl hydrogen sulphate thermally decomposed to give ethene . 2. heated sulphuric acid . to form ethyl hydrogen sulphate .Ethanol reacts with conc.

2.Alkene from C1 to C4 are gases and from C5 to C15 are liquids.Alkene are non polar insoluble in water and dissolve in organic compounds as ether and CCl4 Chemical reactions .Physical Properties ■ 1.

■ Bayer’s reaction: Is used to test for double bond or pi bond where purple KMnO4 (in alkaline medium) is decolorized through the reaction(differentiate between ethane and ethylene) . By burning: b. Oxidation: a. This reaction is called Bayer’s reaction. By using an oxidizing agent (Bayer’ reaction) ■ Oxidizing agent Such as purple potassium permanganate KMnO4 oxidizes ethylene into glycol which is alcohol contains two OH groups on two adjacent carbon atoms and the colour of permanganate is discharged.

Hydrogenation: Is adding of hydrogen to produce corresponding alkane each pi bond needs one mole of hydrogen gas to be broken. Addition Reactions ■ a. .

this reaction is used to detect unsaturated alkenes. b. the red color of bromine is removed and a colorless 1.Halogenation : ■ Halogens react with alkenes by additions. When bromine in carbon tetrachloride is added to ethene. 2 dibromo – ethane(ethene dibromide) is formed .

With hydrogen halides (H . the two carbon atoms which are attached to the double bond carry the same number of hydrogen atoms. giving the corresponding alkyl halide.X ): ■ Alkenes react by addition with hydrogen halides where the (Pi) bond break down. a) If the alkene is symmetrical i. The hydrogen atom is added to one carbon atom of the double bond and the halogen atom is added to the other one. c. The addition products depend on the type of alkene.e. the hydrogen atom is added to any carbon atom and the halogen atom is added to other one . .

. whereas the halogen atom is added to the other carbon poor in hydrogen. the positive part of the reagent is added to the carbon atom which carries a large number of hydrogen atoms and the negative part is added to the carbon atom which carries less number of hydrogen atoms “.b) If the alkene is asymmetrical ■ (the two carbon atoms which attached to the double bond carries different number of hydrogen atoms) the hydrogen atom is added to the carbon atom rich in hydrogen atoms. ■ Markownikoff’s rule : “On adding an asymmetric reagent (HX) or (H – OSO3H) to an asymmetric alkene. This rule is known as “Markownikoff’s Rule”.


This method is considered as industrial method for preparation of ethanol from petroleum: that is why ethanol is petrochemical compound . Addition of water(catalytic hydration): ■ Water is a weak electrolyte contains very small ratio of proton can’t break down the double bond so water is added to alkene in the presence of strong acid as sulphuric acid??? Sulphuric acid reacts with ethylene forming ethyl hydrogen sulphate which hydrolyze into ethanol and sulphuric acid.d.

. The Chemical properties.TO be continued. In part-2 .

2. Polymerization ■ Combination of a large number of small unsaturated molecules called monomers to form a large molecule called polymer. ■ Number of monomers forming the polymer ranges from 100 to 1000000 units. The copolymer formed is considered as the basic unit which continues the polymerization process.Condensation polymerization : Condensation takes place between two different monomers and accompanied by losing a simple molecule such as water .Addition polymerization : It takes place by adding a huge number of unsaturated small molecules to each other to form a very large molecule such as formation of polyethylene. Both monomer and polymer have the same empirical formula. ■ There are two principal methods for polymerization process: 1. .


■ Example for addition polymerization (polyethylene) when ethene is heated under high pressure (about 1000 atmosphere) in the presence of oxygen or hydrogen peroxide as initiator. In the addition polymerization of ethene (pi) bond is broken. then the carbon atoms of each molecule combine by their free electrons with those of other molecules by a single covalent bond to form a long chain of the polymer molecules . poly ethylene is formed its molecular mass reach to about 30.Each carbon atom now has a free electron. . the electrons of this bond are liberated .000 ( notice that the molecular mass of ethene = 28 only).


which will act on unripe fruit. a ripe tomato placed in a sealed bag with green tomatoes will help ripen them.■ Ethylene is the gas that ripens fruit. . Thus. and a ripe fruit emits the gas.

What is an isomer? ■ In organic chemistry.Lots of carbon compounds seem to be isomers. ■ But different arrangements (structures) of the atoms in their molecules. ■ These are called isomers. there are many examples of different compounds which have the same molecular formula as each other. .

.What is an isomer? ■ These compounds are said to be isomers of one another. ■ Isomerism also occurs in inorganic chemistry. but it is less common.





can be used by a living cell. ■ This is because the enzyme in the cell which recognizes glucose is sensitive to only one form. surely they have the same properties. it is important to realize that this can have significant effects in a living system. these small changes in structure can have significant effects on the properties of the substance! ■ But. for example. ■ One optical isomer of glucose. . but the other isomer cannot.If isomers have the same atoms in them. so what's the point? ■ In fact.

■ This can come about in one of three ways: . structural isomerism ■ Which have the atoms of their molecules linked in a different order.There are two types of isomerism common in organic chemistry: 1.




■ Their chemistry is likely to be identical.Chain Isomerism ■ Chain isomers of the same compound are very similar. . ■ There may be small difference in physical properties such as melting or boiling point due to different strengths of intermolecular bonding.

but the chemical properties are usually very similar. positional isomers can have quite different properties .Positional Isomers ■ Positional isomers are also usually similar. ■ There are slight physical differences. ■ However. occasionally.

. for example the next largest alcohol. has four different structural isomers. Positional Isomers ■ A simple example of isomerism is given by propanol: ■ it has the formula C3H8O (or C3H7OH) and two isomers propan-1-ol (n-propyl alcohol. and to the center carbon in the second. ■ The number of possible isomers increases rapidly as the number of atoms increases. I) and propan-2-ol (isopropyl alcohol. II) ■ Note that the position of the oxygen atom differs between the two: it is attached to an end carbon in the first isomer. named butanol (C4H10O).

.Functional Group Isomers ■ Functional group isomers are likely to be both physically and chemically dissimilar.





You Try It! .

How did you do? .







A.P.U. ■ Alkynes are characterized by the following: 1) Unsaturated hydrocarbons.C from corresponding alkanes .Alkynes (acetylenes) ■ They are unsaturated hydrocarbons containing triple bonds (one is strong sigma and the others are weak pi bonds). by Replacing “ane“ by “yne“ numbering carbon atom from the terminal nearer to the triple bond . between carbon atoms. its general formulae ( CnH2n-2 ) 2) Named according to the I.

4) Chemically more active than alkanes due to presence of two weak pi bonds which can be easily broken.3) First member are gases. then liquids. therefore it reacts by addition. 5) Alkynes are insoluble in water. but dissolve in organic solvents. .

Preparation of acetylene (Ethyne)(C2H2) in lab: 1. In lab: From calcium carbide CaC2. The role of copper sulphate is to remove hydrogen sulphide and phosphine which are produced from the impurities in calcium carbide . by dropping water on calcium carbide.

.■ 2. In industry: From natural gas which contains high % of methan by heating to more 1400ºC and cooling suddenly .

Reactions of Alkynes .

Combustion ■ Alkynes are highly inflammable in oxygen producing heat energy. ■ This reaction is used in welding and cutting metals and called oxy acetylene flame . its amount depends on quantity of oxygen (oxy acetylene flame).

Oxy acetylene .

of hydrogen ] : .Addition reactions 1) Hydrogenation [ add.

I2) Acetylene (ethyne) reacts vigorously with halogen . the red colour of bromine is reduced so this reaction is used to test unsaturation (pi bond) in ethyne. the reaction is accompanied with heat and flame in case of chlorine but with bromine water dissolved in carbon tetrachloride. .2) Halogenation :add of halogen (Cl2 –Br2 .

3) With halogen acids [ HCl .HBr .HI ] • Addition of halogen acids to acetylene takes place according to MarkoniKoff’s rule .

■ This reaction is used to prepare acetic acid (ethanoic) from acetaldehyde (Ethanal)by oxidation .Addition of water (catalytic hydration) ■ Catalytic hydration of acetylene gives acetaldehyde.

■ Also is used in preparation ethyl alcohol .









For example. Ether and secondary amines are the best examples of metamerism. ethoxypropane and 1- ethoxypropane are metamers of each other. Metamerism In this type of isomerism. 4. isomers differ in structure because of differences in the distribution of carbon atoms about the functional group. CH3CH2CH2-O-CH2CH3 and CH3-CH2-O-CH2-CH2-CH3 Ethoxypropane 1-Ethoxypropane 5. isomers are in dynamic equilibrium and converts in keto and enol form due to . Tautomerism It is also called as keto-enol isomers as in this type of isomerism.




the rings are planar. unlike the boat or table structures typical of cycloalkanes. due to their aromaticity.Aromatic Compounds ■ Aromatic compounds. . ■ Aromatic compounds are cyclic structures in which each ring atom is a participant in a π bond. including unusual stability. are unsaturated hydrocarbon ring structures that exhibit special properties. They are often represented as resonance structures containing single and double bonds. the bonding is stronger than expected for a conjugated structure. originally named because of their fragrant properties. However. resulting in delocalized π electron density on both sides of the ring. and it is more accurately depicted as delocalized electron density shared between all the atoms in the ring. Due to this connected network of π bonds.

Due to their high ratio of carbon to hydrogen. As they are often unreactive. they are useful as solvents for other nonpolar compounds.Physical properties of aromatic compounds ■ Aromatic compounds are generally nonpolar and immiscible with water. aromatic compounds are characterized by a sooty yellow flame. .

. This stability is lost in electrophilic addition because the product is not aromatic. Instead. the product retains the stability associated with the aromatic π electron system.Reactivity of aromatic compounds ■ The double bonds in aromatic compounds are less likely to participate in addition reactions than those found in typical alkenes. cyclic aromatic compounds undergo electrophilic substitution reactions (reactions in which the ring acts as an nucleophile to a suitable electrophile). When benzene participates in such substitution reactions.

2- dichlorobenzene existed as two isomeric forms. Whilst this is reasonably close to accurate. Structure of Benzene ■ Kekulé Structure Kekulé (1866) bravely proposed that benzene had a cyclic structure with three alternating C=C double and three C-C single bonds. yet it was known that it did not . it cannot be exactly correct since this would require that 1.

. with all the carbon- carbon bond distances the same 1. and thus an irregular hexagonal shape.Resonance structure ■ The Kekulé structure would have the single bonds of longer length than the double bonds.48Å. ■ But spectroscopy had shown that benzene had a planar ring. ■ Since the atoms are the same distance apart.397Å (C-C typically 1. and the only difference is the location of the pi electrons in the two Kekulé structures. C=C typically 1. they are in fact resonance structures of one another.34Å).

■ Because of the delocalization of the π electrons. often the double bonds are represented by a circle in the middle of the hexagon. .

with 6 sp2 hybrid carbons. ■ All the carbon-carbon bonds are of equal length. ■ These p orbitals each have 1 electron inside. ■ Each carbon has an unhybridized p orbital. and all the bond angles are 120°. which lies perpendicular to the plane of the ring.■ This resonance description lets us draw a more realistic representation of benzene. each bonded to one hydrogen atom. . ■ There are therefore 6 electrons in the circle of p orbitals.

. we know alkenes can be oxidized to syn diols (KmnO4) and undergo electrophilic additions with halogens (Br2). ■ Yet the same reactions do not work with benzene. Unusual behavior of Benzene ■ Benzene has much more stability than predicted by the simple resonance delocalized structure. For example. ■ Benzene does not react .benzene is more stable than normal cyclo-alkenes.

■ All three double bonds are retained in the product.■ When a catalyst is added to the benzene bromination reaction. but the reaction is not an addition. . but rather a substitution (a ring hydrogen is substituted for a ring bromine). reaction does occur.

Failures of the Resonance Picture for Aromatics ■ If having these identical resonance structures were the sole cause of this pronounced stability. ■ These cyclic hydrocarbons with alternating double and single carbon carbon bonds are called Annulenes . then ALL structures with conjugated systems of alternating double and single bonds should show analogous enhanced stabilities.

■ Cyclo-octatetraene has been shown to not exist in a planar structure. It exists like this .in fact quite the opposite! ■ Cyclobutadiene has never been isolated and purified because it is so unstable . but instead it adopts a 'tub' like conformation. Rather. molecules like cyclobutadiene and a planar structure like this. cyclo-octatetraene DO NOT exhibit this increased stability . Cyclo-octatetraene does not exist in ■ reacts with itself to form dimers even at low temperatures. and is called [6] annulene.■ Benzene is the 6 membered annulene. ■ For the double bonds to be totally conjugated. the molecule must be planar so that the p orbitals of the pi bonds can overlap.

MO’s of benzene .

■ Even though we have only seen two dimensional MO's previously (ethene. no nodes). ■ 3) The number of nodes increases as the MO's increase in energy. just like for a pi bond). a three dimensional system). therefore six MO's are created.e. allyl systems. and therefore each carbon has an unhybridized p orbital.e. ■ These p orbitals create a continuous ring of orbitals above and below the plane of the carbon atoms. the same basic rules apply. ■ 2) The lowest energy MO is entirely bonding (constructive overlap between all adjacent p orbitals. with the possibility on non- bonding MO's in some cases. ■ 1) Six p orbitals are used in the benzene pi system. . ■ 4) The MO's must be divided between bonding and antibonding. ■ These p orbitals are perfectly aligned for overlap (i. ■ The 6 overlapping p orbitals create a cyclic system of molecular orbitals (i. ■ Benzene has 6 planar sp2 carbons. and so we must turn to Molecular Orbital theory for a fuller answer.■ Benzene's extra stability cannot be explained by resonance alone. bonding.

• Each p orbital contributes one electron. Energy Level Diagram of Benzene • MO's ∏ 4*. This electron configuration is sometimes referred to as a 'closed bonding shell'. is a very stable arrangement. ∏5* and ∏6* are all overall antibonding. and lie above the level of an isolated p orbital (non-bonding line). which happen to be the bonding MO's. • The 6 electrons fill the three lowest MO's. which means we have 6 electrons to accommodate (this is the same number of electrons as 3 ∏ bonds in the Kekulé structure). . This electron configuration of all the bonding MO's filled. and explains the high stability of benzene.

MO theory provides an explanation for this (unexpected) instability. . ■ Cyclobutadiene contains four sp2 hybridized carbons. The MO Picture of Cyclobutadiene ■ Although it is possible to write resonance structures for cyclobutadiene. ■ Again. experimental evidence indicates that it is very unstable. which leaves four p orbitals for the bonding.

This is usually achieved through a planar (or almost planar) arrangement. ■ An antiaromatic compound is one which meets the first three criteria. ■ 3) The unhybridized p orbitals must overlap to form a continuous ring of parallel orbitals. ■ In a more specific. aromatic compounds are defined as those which meet the following criteria: ■ 1) The structure must be cyclic.Aromatic. but delocalization of the pi electrons over the ring results in an increase of the electronic energy. . chemical sense. ■ 2) Each atom in the ring must have an unhybridized p orbital. and contain some number of conjugated pi bonds. ■ 4) Delocalization of the pi electrons over the ring must result in a lowering of the electronic energy. Antiaromatic and Nonaromatic Compounds. allowing for the most efficient overlap.

3.cis-2. . benzene is more stable than 1. overlapping ring of p orbitals cannot be aromatic or antiaromatic.5-hexatriene ■ An antiaromatic compound is less stable than its open chain counterpart. cyclobutadiene is less stable than butadiene.■ Aromatic compounds are more stable than their open chain counterparts. For example. For example 1.3- cyclohexadiene is about as stable as cis. ■ The electronic energy is similar to its open chain counterpart. ■ A cyclic compound that does NOT have a continuous. For example.4-hexadiene.

it must have a continuous ring of overlapping p orbitals. 10. arranged in a planar. Hückel Aromaticity ■ Hückel developed a quick way to predict which of the annulenes would be aromatic. then the system is antiaromatic. ■ If (and only if) the molecule in question meets the criteria for being either aromatic or antiaromatic (i. or almost planar fashion). ■ If the number of pi electrons in the cyclic system is equal to 4N. 6. where N is a whole number integer. ■ Thus systems with 2. … pi electrons are aromatic. then the system is aromatic. 8. then Hückel's rule applies.e. 12. … pi electrons are antiaromatic. where N is a whole number integer. and which would be antiaromatic. ■ Hückel's Rule states that if the number of pi electrons in the cyclic system is equal to (4N+2). ■ Systems with 4. . 14.


Benzene is obtained at 80-82 C. it decomposes into gases and liquids. The most important of these liquids is a heavy black substance known as “ coal tar”. . By fractional distillation of coal tar. we obtain very important organic compounds economically. Preparation of benzene in industry ■ (1) From coal tar: ■ During destructive distillation of coal( heating in absence of air).

Preparation of benzene from aliphatic petroleum derivatives. This method is called catalytic reforming method .2. normal hexane is passed at high temperature on the surface of platinum as a catalyst. ■ A) from normal hexane: In this method.

■ B) polymerization of ethyne By passing ethyne in red hot nickle tube Red hot nickel ball .

From Phenol ■ By passing phenol vapors on the surface of hot zinc powder which reduces phenol to benzene .3.

Preparation of benzene in the lab ■ By dry distillation of sodium benzonate with soda lime .

Naming benzene derivatives .

✓ A special class of cyclic unsaturated hydrocarbons is known as the aromatic hydrocarbons.What are aromatic hydrocarbons? ✓ Aromatic means having a smell. The simplest of these is benzene (C6H6) . and hydrocarbons means that they are composed only from hydrogen and carbon.

Reactions • benzene undergoes substitution reactions in which hydrogen atoms are replaced by other atoms. .

and para. meta.(o-) for two adjacent substituents. it is called the phenyl group. 1.(m-) for two substituents with one carbon between them. Nomenclature  It is similar to the nomenclature for saturated ring systems.  Another nomenclature system uses the prefix ortho.(p-) for two substituents opposite each other. .2-dichlorobenzene o-chlorobenzene  When benzene is used as a substituent.

Practice : .





3. hot benzene will also undergo an addition reaction with chlorine or bromine.2.6-hexachlorocyclohexane. For example. if you bubble chlorine gas through hot benzene exposed to UV light for an hour.4.Addition reactions of benzene ■ In the presence of ultraviolet light (but without a catalyst present). The ring delocalization is permanently broken and a chlorine or bromine atom adds on to each carbon atom. . you get 1.5.

For example: With benzene: • These reactions destroy the electron delocalization in the original benzene ring. but the pressures used tend to be higher. . The reactions are done using the same finely divided nickel catalyst that is used in hydrogenating alkenes and at similar temperatures (around 150°C).Addition of hydrogen ( hydrogenation) ■ Hydrogenation is an addition reaction in which hydrogen atoms are added all the way around the benzene ring. Although the reactions are exothermic overall because of the strengths of all the new carbon-hydrogen bonds being made. there is a high activation barrier to the reaction. A cycloalkane is formed. because those electrons are being used to form bonds with the new hydrogen atoms.

Benzene reactions .

Electrophilic attack substitution (EAS) ■ Step 1: An electrophile attacks the pi electrons of the aromatic benzene ring which results in the formation of a resonance stabilized carbocation. It is endergonic and has high activation energy due to the loss of aromaticity . Electrophilic attack is a very slow process. This carbocation is called the arenium ion and has three resonance contributors.

As opposed to the first step. It is important to note that the carbocation loses a proton where the electrophile attacked the benzene ring. this step is fast and exergonic because aromaticity is regained. .■ Step 2: The carbocation intermediate is attacked by a base and loses a proton. These electrons are used to reform a pi bond and restore aromaticity.

I) . Cl.Aromatic Halogenation ■ Functional groups: halides (Br.

Chlorine mechanism example .


Uses of aryl halides ■ Aryl halides are produced in large scales and are used as insecticides. trichloro ethane. Its poisonous effect is due to the presence of the group ( CH. the most important one is DDT which is dichloro diphenyl.CCl3) in the molecule which dissolves in the fatty tissue of the insect and kill it. It was called the ugliest compound in the history of chemistry for its environmental problems .

Aromatic nitration .

dissociation of H2SO4 .Nitration mechanism 1.

2-HNO3 reaction with H2SO4 .

3-Electrophile attack of hydronium ion .

nucleophile attack of water and restoring aromaticity .4.

These compunds burn rapidly. carbon besides oxygen which is the oxidizing agent. and a great amount of heat and gases are produced accompanied by explosion. to form the strong bonds. This is due to the weakness of the bond between N and O (N-O).Poly nitro organic compounds are explosive ■ They are explosive beacuase theycontain their own fule. . between C and O (C-O) in carbon dioxide and the bond between (N-N) in nitrogen molecule.

and still produced until now.TNT ( trinitrotoluene) ■ It is one of the explosive nitro organic compounds which was produced by millions of tons through the second world war. This compound is prepared by the reaction between toluene and a mixture of concentrated nitric and sulfuric acid ( ratio 1:1) .

Aromatic sulfonation .

Mechanism .


Detergents ■ The detergent industries depend mainly on the aromatic sulphonic acid compounds after the treatment with caustic soda to obtain the water soluble sodium salt. .

is an ionic group which is hydrophilic. it is a long carbon chain which is hydrophobic and the other part(head).■ The molecule of detergent is composed of two parts (tail). .




Friedel -Crafts alkylation .



Freidel acetylation reaction .

Mechanism .


.Question This reaction will give us iso propyl benzene not propyl benzene.

.This is because the positive charge will form on the secondary carbon not the primary carbon.

Naming di substituted benzene ring .



para directing activators ( electron donating groups) ■ First. The red dots represent the positions of carbonations in the resonance intermediates .Ortho. meta and para locations. we have to know the resonance structure of the carbocation intermediates for ortho.

.Ortho. para directors Both ortho and para locations are more preferable as they bring the positive charge ( carbocation) near the electron donating substituent.

Meta directors Meta directing groups include The middle structure is the most preferable one .

uk/organicprops/arenes/other.chemguide.html ■ links ■ 5uMZeVTM_cSb3NeDswlM ■ https://www.php ■ http://www.


and according to carbinol group. to learn the detection of functional groups by spectral analysis. and NaOH Skills: Students will go to Cairo Univ. Classification of alcohols according to the functional group. ethanol o c.20 Connect functional groups with chemical and physical properties of organic compounds.LO.3. Conduct research on their industrial applications. Nomenclature • 2. Oxidation reactions to determine the presence of ethanol • 6.Industrial application of: o a. Differentiate between phenols. Key Concepts: • 1. ethylene glycol • 7. methanol. glycerol o d. Essential Questions: How can rice straw be converted from an environmental disaster to an economic value? . Preparation theoretically from alkanes and alkyl halides • 5. Identify and describe aliphatic alcohols and will be able to prepare them and test for their presence. • 3. methanol o b. Prepare experimentally by fermentation • 4.

Conduct research on their industrial application. Reactions: o a.21 Study esters and will be able to prepare esters. Key Concepts: • 1. write the formula and structure and create a three dimensional model of the molecules. food. fabrics. Preparation of aspirin • 3. determine their presence. Nomenclature according to the origin • 2. Application of esters in perfumes and food industry. plastics related and what do they have to do with Egyptian industry? . Essential Questions: How are flavours.LO.preparation of saponification • 4. acidic hydrolysis of ethyl acetate o b.3. oils. Skills: Students will produce an ester in the laboratory. alkaline hydrolysis. polymers.

■Hydrocarbon Derivatives .

Br2. I2.■ Introduction – Hydrocarbon derivatives are formed when one or more hydrogen atoms is replaced by an element or a group of elements other than hydrogen.) can all add to a hydrocarbon to form am alkyl halide. Cl2. ■ When naming the halogen the –ine ending is replaced by –o ■ Fluorine becomes fluoro ■ Chlorine becomes chloro ■ Bromine becomes bromo ■ Iodine becomes iodo . – Halogens (F2.


■ Common examples of organic halides.

– Alkenes can also add to each other in an addition reaction to form long chains of carbon compounds. . ■ Functional groups usually have multiple bonds or lone pairs of electrons that make them very reactive. ■ this is called polymerization – The atom or group of atoms that are added to the hydrocarbon are called functional groups.

 Alcohols  An alcohol has a hydrogen replaced by a hydroxyl (-OH) group.  The name of the hydrocarbon that was substituted determines the name of the alcohol.  The alcohol is named using the hydrocarbon name and adding the suffix – ol. . ○ If methane is substituted with an OH group it becomes methanol ○ If a pentane group is substituted with an OH group it is pentanol. ○ For alcohols with more than two carbon atoms we need the number the chain so as to keep the alcohol group as low as possible.

The IUPAC name is given above each structural formula. and the common name is given below.■ Four different alcohols. .

which does contain oxygen. Gasohol contains ethyl alcohol. is likely during the dates shown on the pump. Gasoline is a mixture of hydrocarbons (C8H18 for example) that contain no atoms of oxygen. The addition of alcohol to gasoline. C2H5OH. adds oxygen to the fuel. An atmospheric inversion. . so that is when the ethanol is added. Since carbon monoxide forms when there is an insufficient supply of oxygen. with increased air pollution. the addition of alcohol to gasoline helps cut down on carbon monoxide emissions. therefore.

– An alcohol with three OH groups is called a triol (sometimes called a glycerol). . – If an alcohol contains two OH groups it is a diol (sometimes called a glycol).– The OH group is polar and short chain alcohols are soluble in both nonpolar alkanes and water.

. The IUPAC name is given above each structural formula. and the common name is given below.■ Common examples of alcohols with one. two. and three hydroxyl groups per molecule.

and Ketones – An ether has a general formula ROR’ ■ Diethyl ether for example would have the formula CH3CH2OCH2CH3 – An aldehyde has a carbonyl group (carbon double bonded to an oxygen) attached to a terminal carbon atom – A ketone has a carbonyl group attached to an internal carbon atom. Aldehydes. .■ Ethers.

with the IUPAC name above and the common name below each formula. .■ The carbonyl group (A) is present in both aldehydes and ketones. as shown in (B). (C) The simplest example of each.

Chapter Twenty-Two Organic and Biological Molecules

Organic chemistry

Hydrocarbons Derivatives of hydrocarbons

Aromatic Aliphatic

(open chain)

Saturated Unsaturated

Alkanes Alkenes Alkynes

What are aromatic hydrocarbons?

✓ Aromatic means having a smell, and hydrocarbons means that they are composed
only from hydrogen and carbon.
✓ A special class of cyclic unsaturated hydrocarbons is known as the aromatic
hydrocarbons. The simplest of these is benzene (C6H6)

• benzene undergoes substitution
reactions in which hydrogen atoms are
replaced by other atoms.

 It is similar to the nomenclature for saturated ring systems.

 Another nomenclature system uses the prefix ortho- (o-) for two
adjacent substituents, meta- (m-) for two substituents with one
carbon between them, and para- (p-) for two substituents
opposite each other. 1,2-dichlorobenzene
 When benzene is used as a substituent, it is called the phenyl

Practice :

☺☺☺ Reference:  Zamdahl 7th edition .❖ Benzene is the simplest aromatic molecule. More complex aromatic systems can be viewed as consisting of a number of “fused” benzene rings.


org/chemistry/the-mole-concept/empirical-and-molecular- formulas/1013-distinguish-between-empirical-molecular-and-structural-formulas-ib- chemistry-sl ■ formulas/125-determine-empirical-formula-from-the-percent-composition-or-from- other-data-ib-chemistry-sl .Sources: ■ https://socratic.

hydrogen bonds. ■ c.highly polar bonds answer :B .covalent bonds.Question ■ Carbon shows a very strong tendency to form: ■ a. ■ b. ■ d.ionic bonds.

5 ■ Answer : C .2 ■ b.4 ■ d.3 ■ c.■ How many covalent bonds can a carbon atom usually form? ■ a.

metals.■ Carbon atoms readily join with atoms of: ■ a.nonmetals. ■ Answer : C . ■ d. ■ b.both other elements and carbon. ■ c.carbon only.

alcohols and acids. ■ ANSWER : A .oxides and carbonates. c. b. d.aldehydes and ketones.ethers and esters.■ Organic compounds are defined as all covalently bonded compounds containing carbon except a.

■ The diversity of organic compounds is so great because carbon a.has many isotopes. c.compounds are very reactive. b.compounds have many isomers. ■ ANSWER : C . d.has many allotropes.

geometric isomers compounds ■ Answer :A .In which of the following are the atoms bonded in a different order? a.structural isomers b.three-dimensional models d.

structural isomers b.geometric isomers c.three-dimensional models compounds ■ Answer : B .■ In which of the following are atoms bonded in the same order but arranged differently in space? a.

Saturated v. Unsaturated fats Saturated with H) .



but they are still weaker than the inorganic acids like: hydrochloric acid and sulfuric acid. . They are aromatic or aliphatic carboxylic acids.Carboxylic acids ■ They are the most acidic organic compounds. ■ They are known by the presence of a carboxylic group.

■ The monocarboxylic aliphatic acids are named fatty acids because they present in fats in form of esters with glycerol. .■ The carboxylic group which is COOH is composed mainly from 2 functional groups: the carbonyl group(C=O) and the hydroxyl group (- OH).

Examples of carboxylic acids Phthalic acid Benzoic acid Oxalic acid .

Nomenclature of carboxylic acids ■ Common names:- The carboxylic acids are usually named by common names which are derived from the Latin name. .

IUPAC Nomenclature ■ The IUPAC system of nomenclature assigns a characteristic suffix to these classes. it is always is given the #1 location position in numbering and it is not necessary to include it in the name. ■ Since a carboxylic acid group must always lie at the end of a carbon chain. . The –e ending is removed from the name of the parent chain (the corresponding alkane)and is replaced -oic acid.

. ■ Preparation of acetic acid in industry: ➢ biological method:- ■ The oxidation of diluted alcoholic solutions by the atmospheric oxygen in the presence of vinegar bacteria. ➢ Chemical method:- ■ Also by the catalytic hydration of acetylene where acetaldehyde is produced and then easily oxidized to the acid.Acetic acid ■ It is a monocarboxylic aliphatic acid.

General prosperities of carboxylic acids .

odorless. and insoluble in water. ■ They are completely miscible with water. ■ As the molecular weight increases they become solids. ■ The following members are oily and sparingly soluble in water. .Physical properties of carboxylic acids ■ The physical properties of organic compounds are graduated by increasing the molecular weight. ■ The first four members are corrosive liquids and they have a pungent irritating odor.

.The boiling point ■ The boiling point of the carboxylic acids compared to those of alcohols which have the same number of carbon atoms is higher due to the presence of the hydrogen bond as each acid molecule is attached to another by the hydrogen bond.

hydroxides. .Chemical properties of carboxylic acids ■ The acidic property of the carboxylic acids appears in their reactions with metals above hydrogen in the electrochemistry series. ■ The react with alcohols and form ester and water. carbonate. and bicarbonate salts to form organic salts.

. ■ Ethanol can be prepared by this method which is the opposite the oxidation of alcohols to produce acids.Reactivity of carboxylic acids ■ They are reduced by hydrogen in the presence of copper chromate as a catalyst at 200 degree Celsius.

Ester formation test Acids react with alcohols to produce esters which have a pleasant odor. 2. Acidity test When the acid is added to sodium carbonate or bicarbonate.Detection of carboxylic acids 1. effervescence takes place and CO2 gas is produced and turbid the lime water. .

.Aromatic carboxylic acids ■ They contain one or more carboxylic group attached to a benzene ring. ■ They are more active and less volatile and soluble in water.

(4%) vinegar in homes. ■ Acetic acid: (100%) colorless corrosive liquid which has a pungent odor. .Organic acids in our life ■ Formic acid: Produced by ants to defend themselves.

It prevents the growth of bacteria by decreasing the PH.■ Benzoic acid: Sparingly soluble in water. ■ Citric acid: It is found in fruits like: orange and lemon. It can be converted to its sodium or potassium salts to be soluble in water. Sodium benzoate(1%) prevents the growth of fungi in food. It’s also used to retain the color and the taste of some fruits .

. which decreases the biological functions in the human body. It can be found in fruits and vegetable.■ Lactic acid: Found in milk as a result of secretion of some enzymes by certain bacteria in milk sugar. The lack of this vitamin leads to Escrapot disease. It is also produced by the human body as a result of herd work. ■ Ascorbic acid (Vitamin C): Humans need this vitamin in small quantities.

. ■ Amino acids: They are organic acids derivatives. It is formed by replacing one hydrogen atom in the alkyl group by amino group (-NH3).■ Salicylic acid: It is used in the formation of aspirin but it causes stomach bleeding. Proteins are considered as a polymers of amino acids. There are only 20 amino acids found in natural proteins.

■ The odor of the ester decreases by increasing the molecular weight of the alcohol and the acid used in the formation. ■ They have pleasant smell which is responsible for the odor and flavor of fruits and flowers. ■ Fats and oils are derived from high fatty acids and trihydric alcohols. ■ They can be liquids or odorless waxy solids. .ESTERS ■ They are the products of the reaction between carboxylic acids and alcohols.

The alkyl group is named like a substituent using the -yl ending. This is followed by a space.Nomenclature of Esters ■ Esters Systematic names of esters are based on the name of the corresponding carboxylic acid. The acyl portion of the name (what is left over) is named by replacing the -ic acid suffix of the corresponding carboxylic acid with -ate. .

.Physical properties of esters ■ Most of esters are liquids which is much lower boiling point than those of corresponding acids and alcohols due to the absence of the polar hydroxyl group.

.Chemical properties of esters ■ 1-hydrolysis: (reverse of ester formation) Alcohol and acid can be produced from hydrolysis of ester.(acid hydrolysis)use the dilute mineral acids as a catalyst. Methods of hydrolysis: 1. 2-(alkaline hydrolysis): by heating the ester with aqueous alkali to produce alcohol and salt of the acid.

Ammonolysis ■ Esters can react with ammonia and give alcohol and acid amide. .

so they are used in food industries as flavors. .Esters as flavor ■ Esters have pleasant smell and taste.

■ Saponification is the hydrolysis of fat or oil in the presence of strong alkali which is principle reaction in the manufacturing of soap and glycerol. .Esters as oil and fats ■ Fats and oils are esters produced from the reaction between 3 molecules of fatty acids and glycerol which is trihydric alcohol.

one of them is dibasic acid and the other is dihydric alcohol. ■ The most common ester is Darcon fibers which is prepared by the reaction between terphthalic acid and ethylene glycol. .Esters as polymers ■ Polyesters are polymers produced from the condensation of 2 monomers.

Esters as medical drugs .

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