VII. Organic J Deutsch 2003 2 Organic compounds contain carbon atoms which bond to one another in...

VII. Organic

J Deutsch 2003 2

Organic compounds contain carbon atoms which bond to one another in chains, rings, and networks to form a variety of structures. Organic compounds can be named using the IUPAC system. (3.1ff)

J Deutsch 2003 3

Hydrocarbons are compounds that contain only carbon and hydrogen.

Saturated hydrocarbons contain only single carbon-carbon bonds.

Unsaturated hydrocarbons contain at least one multiple carbon-carbon bond. (3.1gg)

J Deutsch 2003 4

Homologous series of hydrocarbons:

Saturated hydrocarbons– Alkanes

• Only single bonds between carbons

• Name ends in

___ane

• General formula CnH2n+2

• Methane CH4

Ethane C2H6

Unsaturated hydrocarbons– Contain at least one

double or triple bond

– Alkenes• Contain one double bond

• Name ends in ___ene

• General formula CnH2n

– Alkynes• Contain one triple bond

• Name ends in ___yne

• General formula CnH2n-2

J Deutsch 2003 5

Table Q gives the general formula and examples (name and structure) of the homologous series of hydrocarbons.

J Deutsch 2003 6

Regents Question: 06/03 #24

Which element has atoms that can form single, double, and triple covalent bonds with other atoms of the same element?

(1)hydrogen

(2) oxygen

(3) fluorine

(4) carbon

J Deutsch 2003 7

Table P gives the prefix used to name the first 10 hydrocarbons in an homologous series.

J Deutsch 2003 8

The prefix of the name tells you how many carbons in the chain.The suffix tells you the type of hydrocarbon.

Pentene

C5H10

Butene

C4H8

Propene

C3H6

Ethene

C2H4

Pentane

C5H12

Butane

C4H10

Propane

C3H8

Ethane

C2H6

Methane

CH4

Pent

But

Prop

Eth

Meth

Prefix

Pentyne

C5H8

5

Butyne

C4H6

4

Propyne

C3H4

3

Ethyne

C2H2

2

1

Number of Carbons

AlkaneCnH2n+2

AlkeneCnH2n

Alkyne CnH2n-

2

Example

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Which hydrocarbon is saturated?

(1) propene

(2) ethyne

(3) butene

(4) heptane

Alkanes are saturated hydrocarbons.

J Deutsch 2003 10

A structural formula show the way the atoms are arranged.

Methane Ethane H H H

H C H H C CH

H H HEach line represents a covalent

bond - a shared pair of electrons.

J Deutsch 2003 11

A structural formulas show the way the atoms are arranged.

propene H H

H C C C H

H H

ethyne H C C H

The double bonds makes this hydrocarbon an alkene

The triple bonds makes this hydrocarbon an alkyne

J Deutsch 2003 12

Regents Question: 01/03 #13The empirical formula of a compound is CH2

Which molecular formula is correctly paired with a structural formula for this compound?

J Deutsch 2003 13

Chains of carbons can be branched

A carbon group connected to a chain is called an alkyl group.

To name the alkyl group, use the prefix for the number of carbons and add -yl.

-CH3

H

H C

HMethyl

-C2H5

H H

H C C

H HEthyl

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Carbon always has 4 bonds. Hydrogen always has 1 bond Oxygen always has 2 bonds Nitrogen always has 3 bonds

H O or O N

C or C or C

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Which structural formula is incorrect?

Carbon always has four bonds.

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Naming hydrocarbons with alkyl groups: Find the longest continuous chain of

carbons. This is the backbone. Find the name of the backbone.

Find the name of the alkyl group (or groups) attached to the backbone.

Name the alkyl group and then the name of the backbone.

Use a number to indicate which carbon the alkyl group is attached to if necessary.

J Deutsch 2003 17

4

H

H C H

H H H H H

H C C C C C C H

H H H H H H 4 3 256

Find the name of this hydrocarbon.

Find the longest chainFind the alkyl group

hexanemethyl

1 2 3 5 6 1

Counting from each direction find the carbon where the alkyl group is attached (the lower number)

3-

J Deutsch 2003 18

H

H C H

H C H

H H H H

H C C C C C H

H H H H H

The longest chain does not have to be drawn straight.

3-methylhexane

H

H C H

H C H

H H H H

H C C C C C H

H H H H H

J Deutsch 2003 19

Chains of carbons can form rings

Use a prefix cyclo when a ring is formed To make a ring, two Hydrogen atoms are

removed

Cyclopentane is a 5 carbon ring with all

single bonds.

J Deutsch 2003 20

• Organic acids, alcohols, esters, aldehydes, ketones, ethers, halides, amines, amides, and amino acids are categories of organic molecules that differ in their structures. Functional groups impart distinctive physical and chemical properties to organic compounds. (3.1hh)

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Functional Groups: Functional groups are groups of atoms that have

special chemical properties and which define the chemistry of an organic compound.

The following are common functional groups:

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Reference Table R lists all the functional groups.

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Reference Table R Cont’d.

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Which pair below contains an alcohol and an acid?

(1) a and b (3) b and d

(2) a and c (4) c and d

Regents Question: 06/03 #44Given the formulas of four organic

compounds:

J Deutsch 2003 25

Naming Halocarbons (-X)

Halocarbons (or halides) have a halogen (F, Cl, Br, I) in place of a hydrogen

Name the halogen first (fluoro, chloro, bromo, iodo) then name the alkane

If there are more than 2 carbons in the chain, use a number to indicate which carbon the –X group is attached to. (Number from the direction that gives the smallest number)

H H Cl

H C C C H

H H H

H Br H H

H C C C C H

H H H H

1-chloropropane 2-bromobutane

J Deutsch 2003 26

H OH H

H C C C H

H H H

Naming Alcohols (-OH) Alcohols have the hydroxyl group -OH The prefix is the number of carbons in the longest

chain – Name the alkane and drop the letter e

The suffix is ol If there are more than 2 carbons in the chain, use a

number to indicate which carbon the –OH group is attached to. (Number from the direction that gives the smallest number)

H H OH

H C C C H

H H H

1-propanol 2-propanol

J Deutsch 2003 27


Which compound is an alcohol?

(1)propanal

(2) ethyne

(3) butane

(4) methanol

J Deutsch 2003 28

Naming Ethers (-O-)

Ethers have an Oxygen in the chain of carbons

Name the alkyl groups on either side of the O that is in the chain

If both alkyl groups are the same it is named once with the prefix DI in front of it.

H H H

H C C O C H

H H H

Methyl ethyl ether

H H

H C O C H

H H

Dimethyl ether

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H H O

H C C C H

H H

Naming Aldehydes (-CHO)

Aldehydes have a double bonded Oxygen on the last carbon in the chain.

Name the alkane, drop the e and add __al

propanal

O

H C H

methanal

J Deutsch 2003 30

H H O H

H C C C C H

H H H

Naming Ketones (-CO-)

Ketones have a double bonded Oxygen on a carbon in the middle of the chain. (Not the last carbon)

Name the alkane, drop the e and add __one If there are more than 4 carbons in the chain, use a

number to indicate the location of the =O

butanone 3-pentanone

H H O H H

H C C C C C H

H H H H

J Deutsch 2003 31

H H O

H C C C OH

H H

Naming Organic Acids (-COOH)

Acids have a double bonded Oxygen and an –OH on the last carbon in the chain.

Name the acid, drop the e and add __oic acid

Propanoic acid Pentanoic acid

O H H H H

HO C C C C C H

H H H H H

This is OH and not HO…the Carbon is bonded to the O

J Deutsch 2003 32

H H

H C C NH2

H H

Naming Amines (-NH2)

Amines have a nitrogen bonded to the carbon chain. The nitrogen may have two, one or no hydrogen atoms bonded to it.

Name the alkane, drop the e and add __amine If there are more than two carbon atoms, use a number

to indicate which carbon the N is attached to.

ethanamine 2-Pentanamine

H NH2 H H H

H C C C C C H

H H H H H

J Deutsch 2003 33

H O

H C C OH

H

Name the folowing:

H OH H H H

H C C C C C H

H H H H H

H H O H H H

H C C C C C C H

H H H H H

H O

H C C H

H

H H H H

H C C C C H

H H

H H H H

H C C C N H

H H H Ethanoic acid 1-Propanamine

Ethanal 2-butene

3-hexanone 2-pentanol

J Deutsch 2003 34


Which compound is classified as a hydrocarbon?

(1)Ethane

(2) Ethanol

(3) chloroethane

(4) ethanoic acid

J Deutsch 2003 35


Which pair of compounds are alcohols?

J Deutsch 2003 36


Which type of organic compound is represented

by the structural formula shown below?

(1) aldehyde

(2) alcohol

(3) ether

(4) ester

J Deutsch 2003 37

Isomers of organic compounds have the same molecular formula but different structures and properties. (3.1ii)

H H H H H

H C C C C C H

H H H H H

H H H H

H C C C C H

H H H

H C H

H

Pentane C5H12 Methylbutane C5H12

J Deutsch 2003 38

Examples of isomers:

1-butanol (C4H9OH) diethyl ether (C2H5OC2H5)

propanal (C2H5CHO) 2-propanone (CH3COCH3)

4 Carbon, 10 Hydrogen, 1 Oxygen

3 Carbon, 6 Hydrogen, 1 Oxygen

Isomers have the same chemical formulas but different structural formulas.

J Deutsch 2003 39


Which compound is an isomer of pentane?

(1) butane

(2) propane

(3) methyl butane

(4) methyl propane

J Deutsch 2003 40

Regents Question: 06/02 #19Which formula is an isomer of butane?

J Deutsch 2003 41


Given the structural formula for butane:

Draw the structural formula for an isomer of butane.

H H H

H C C C H

H H

H C H

H

J Deutsch 2003 42

Regents Question: 01/03 #18Which compound has an isomer?

J Deutsch 2003 43

In a multiple covalent bond, more than one pair of electrons are shared between two atoms.

Alkenes have one double bond

H H

C C

H H

Alkynes have one triple bond

H C C H

Ethene C2H4

Ethyne C2H2

J Deutsch 2003 44

Unsaturated organic compounds contain at least one double or triple bond. (5.2e)

Alkenes and Alkynes are unsaturated.

By breaking the multiple bond in alkenes and alkynes, more hydrogen atoms can be added

Alkanes are saturated.

Alkanes do not have multiple bonds, therefore, they already have as many

hydrogen atoms as they could possibly hold.

J Deutsch 2003 45


In saturated hydrocarbons, carbon atoms are bonded to each other by

(1) single covalent bonds, only

(2) double covalent bonds, only

(3) alternating single and double covalent bonds

(4) alternating double and triple covalent bonds

J Deutsch 2003 46

Types of organic reactions include: addition, substitution, polymerization, esterification, fermentation, saponification, and combustion. (3.2c)

J Deutsch 2003 47

Cl Cl

H C C H

H H

Organic Reactions-Addition Addition

– H2, Cl2, Br2, HCl, HBr is added to an unsaturated hyrdrocarbon. Both atoms are added to where the double (or triple) bond was located.

– Key to look for – Unsaturated hydrocarbon reactant and one product.

H H

C C

H H

+ Cl2 H H

C C

H H

J Deutsch 2003 48

Organic Reactions-Addition Cont’d

H H

H C C H

H H

H H

C C

H H

+ H2 H H

C C

H H

Addition of hydrogen H2 Can be used to saturate and unsaturated hydrocarbon. It uses a catalyst

such as platinum (Pt)

Pt

J Deutsch 2003 49


Which formula correctly represents the product of an addition reaction between ethene and chlorine?

(1)CH2Cl2

(2) CH3Cl

(3) C2H4Cl2

(4) C2H3Cl

J Deutsch 2003 50

H Cl

H C C H

H H

Organic Reactions-Substitution

Substitution– A halogen is reacted with a saturated

hydrocarbon. One of the halogen atoms substitutes one of the hydrogen atoms.

– Key to look for – Saturated hydrocarbon reactant and two product.

H H

H C C H

H H

+ Cl2 UV

+ HCl

J Deutsch 2003 51

Organic Reactions-Polymerization

Polymerization – joining many small molecules together to form a large molecule– A single unit is called a monomer – Many monomers are bonded together to form a

polymer– Polymers can be natural or artificial

Natural Polymers Artificial Polymers

Protein Polyester

Rubber Nylon

Cellulose Styrofoam

J Deutsch 2003 52


The process of joining many small molecules

into larger molecules is called

(1) neutralization

(2) polymerization

(3) Saponification

(4) substitution

J Deutsch 2003 53

Regents Question: 06/03 #45Which type of reaction is represented by the

equation below?

Note: n and n are very large numbers equal to about 2000.

(1) Esterification (3) saponification

(2) fermentation (4) polymerization

J Deutsch 2003 54

Organic Reactions-Esterification

Esterification – making an ester by combining an alcohol with an organic acid

H H

H C C OH

H H

O H

HO C C H

H

+

H H

H C C O

H H

O H

C C H

H

+ H2O

J Deutsch 2003 55

H H O

H C C C OH

H H

Naming Esters (-COOC-)

Esters have a double bonded Oxygen and an –O– bonded to another carbon.

Name the alkyl group that came from the alcohol. Name the acid but drop __ic acid and replace it with ate.

Propanoic acid 1-Pentanol

H H H H H

HO C C C C C H

H H H H H

Propanoic acid + pentanol Pentyl propanoate + water

J Deutsch 2003 56

H H O

H C C C O

H H

H H H H H

C C C C C H

H H H H H

H HO

Propanoic acid 1-Pentanol

Pentyl propanoate

Making an ester by removing water from an acid and an alcohol

J Deutsch 2003 57

Name the ester:

H O H

H C C O C H

H H

Determine which side was the alcohol and which side was the acid by drawing a line through the oxygen in the chain. The side with the double bonded O was the acid.

Acid Alcohol

Alcohol will make you yl if you ate the acid.

MethylEthanoate

Methyl ethanoate

J Deutsch 2003 58


Given the ester: ethyl butanoate

a. Draw the structural formula for this ester.

b. Determine the gram formula mass of this ester.

H H H O

H C C C C O

H H H

H H

C C H

H H

C 6 x 12 = 72

O 2 x 16 = 32

H 12 x 1 = 12

116 gEven if you got the structure wrong but you got the correct

mass for the structure you drew, you got one point.

J Deutsch 2003 59

Amides (-CON) are made by reacting an organic acid with ammonia or with an

amine.

H O H

H C C N C H

H H H

H O

H C C N H

H H

From ammonia (NH3) From amine

(CH3NH2)

J Deutsch 2003 60

H H O

H C C C OH

H H

Naming Amides (-CON-)

Amides have a double bonded Oxygen and a Nitrogen.

Name the alkyl group that came from the amine. Name the acid but drop __oic acid and replace it with amide.

Propanoic acid 1-Pentanamine

H H H H H

H2N C C C C C H

H H H H H

Propanoic acid + 1-pentanamine Pentyl propanamide + water

J Deutsch 2003 61

H H O

H C C C

H H

H H H H H

N C C C C C H

H H H H H H

OH H

Propanoic acid 1-Pentanamine

Pentyl propanamide

Making an amide by removing water from an acid and an amine

J Deutsch 2003 62

Amino acids have both an amine group and an acid group.

An amino acid is a compound that has an amine group on one side and an acid group on the other.

O R H

HO C C N

H H

R is the only part that changes in different amino acids.

J Deutsch 2003 63

Proteins are polymers of amino acids

O R

HO C C N

H H

O R

C C N H

H H

O R

HO C C N H

H H

Remove water

J Deutsch 2003 64

Organic Reactions-Fermentation

Fermentation – yeast and bacteria can make ethanol and carbon dioxide by breaking down sugar using an enzyme.

– The alcohol can be used to make beer and wine,– The carbon dioxide can be used to make bread rise or make the bubbles in beer and champagne.

C6H12O6 2C2H5OH + 2CO2

Enzyme

J Deutsch 2003 65

Organic Reactions-Saponification Saponification is a reaction in which a lipid

(fat or oil) is used to make soap.

J Deutsch 2003 66

Organic Reactions-Combustion

Combustion – Burning– Combining with oxygen to produce carbon

dioxide and water

Burning Methane CH4 + 2O2 CO2 + 2H2O

Burning Octane 2C8H18 +25O2 16CO2 + 18H2O

Burning Ehtanol C2H5OH + 3O2 2CO2 + 3H2O

J Deutsch 2003 67


In which reaction is soap a product?

(1) addition

(2) substitution

(3) Saponification

(4) polymerization

VII. Organic J Deutsch 2003 2 Organic compounds contain carbon atoms which bond to one another in...

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