VII. Organic

1
VII. Organic
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)
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)
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Homologous series of hydrocarbons

• Saturated hydrocarbons
• Alkanes
• Only single bonds between carbons
• Name ends in ___ane
• General formula CnH2n2
• 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

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Table Q gives the general formula and examples
(name and structure) of the homologous series of
hydrocarbons.
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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?
• hydrogen
• (2) oxygen
• (3) fluorine
• (4) carbon

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7
Table P gives the prefix used to name the first
10 hydrocarbons in an homologous series.
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The prefix of the name tells you how many carbons
in the chain.The suffix tells you the type of
hydrocarbon.
Prefix
Number of Carbons
Example
Alkane CnH2n2
Alkyne CnH2n-2
Alkene CnH2n
Methane CH4
Meth
1
Ethene C2H4
Ethane C2H6
Eth
Ethyne C2H2
2
Propene C3H6
Propane C3H8
Prop
Propyne C3H4
3
Butene C4H8
Butane C4H10
But
Butyne C4H6
4
Pentene C5H10
Pentane C5H12
Pent
Pentyne C5H8
5
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Regents Question 06/03 21
Which hydrocarbon is saturated? (1) propene (2)
ethyne (3) butene (4) heptane
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Alkanes are saturated hydrocarbons.
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A structural formula show the way the atoms are
arranged.

• Methane Ethane
• H H H
• H C H H C C H
• H H H

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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

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Regents Question 01/03 13
The empirical formula of a compound is CH2 Which
molecular formula is correctly paired with a
structural formula for this compound?
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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 H Methyl
-C2H5 H H H C C H H Ethyl
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Carbon always has 4 bonds.

• Hydrogen always has 1 bond
• Oxygen always has 2 bonds
• Nitrogen always has 3 bonds

C or C or C
H O or O N
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Regents Question 08/02 42
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.

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Find the name of this hydrocarbon.
H H C H H H H H H
H C C C C C C H
H H H H H H
2
5
6
1
2
5
6
1
4
3
3
4
hexane
methyl
3-
Counting from each direction find the carbon
where the alkyl group is attached (the lower
number)
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The longest chain does not have to be drawn
straight.
H
H C H
H C H H
H H H H C C C
C C H H H H H H
3-methylhexane
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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.
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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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Reference Table R lists all the functional groups.
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Reference Table R Contd.
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Regents Question 06/03 44
Given the formulas of four organic compounds
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
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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)

1-chloropropane
2-bromobutane
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
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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)

1-propanol
2-propanol
H OH H H C C C H H
H H
H H OH H C C C
H H H H
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Regents Question 08/02 20

• Which compound is an alcohol?
• propanal
• (2) ethyne
• (3) butane
• (4) methanol

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27
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.

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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
methanal
H H O H C C C
H H H
O H C H
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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 C C C
C H H H H
H H O H H H C
C C C C H H H
H H
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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
H H O H C C C
OH H H
O H H H H HO C
C C C C H H
H H H
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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 H H C C NH2
H H
H NH2 H H H H C
C C C C H H H
H H H
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Name the folowing
H H H H H C
C C N H H H H

H O H C C OH
H
Ethanoic acid
1-Propanamine
H O H C C H
H
H H H H H C
C C C H H
H
2-butene
Ethanal
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
2-pentanol
3-hexanone
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Regents Question 06/02 17

• Which compound is classified as a hydrocarbon?
• Ethane
• (2) Ethanol
• (3) chloroethane
• (4) ethanoic acid

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Regents Question 06/02 48
Which pair of compounds are alcohols?
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35
Regents Question 01/03 49
Which type of organic compound is represented by
the structural formula shown below? (1)
aldehyde (2) alcohol (3) ether (4) ester
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36
Isomers of organic compounds have the same
molecular formula but different structures and
properties. (3.1ii)
Pentane C5H12
Methylbutane C5H12
H H H H H C C C
C H H H H H C
H H
H H H H H H C C C
C C H H H H H H
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Examples of isomers
1-butanol (C4H9OH) diethyl ether
(C2H5OC2H5)
propanal (C2H5CHO) 2-propanone
(CH3COCH3)
Isomers have the same chemical formulas but
different structural formulas.
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Regents Question 06/03 25
Which compound is an isomer of pentane? (1)
butane (2) propane (3) methyl butane (4) methyl
propane
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39
Regents Question 06/02 19
Which formula is an isomer of butane?
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40
Regents Question 08/02 55
Given the structural formula for butane Draw
the structural formula for an isomer of butane.
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Regents Question 01/03 18
Which compound has an isomer?
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42
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
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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.
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Regents Question 01/03 25
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
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45
Types of organic reactions include addition,
substitution, polymerization, esterification,
fermentation, saponification, and combustion.
(3.2c)
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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.

Cl Cl H C C H H H
H H C C H H
H H C C H H
Cl2
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Organic Reactions-Addition Contd
Addition of hydrogen H2 Can be used to saturate
and unsaturated hydrocarbon. It uses a catalyst
such as platinum (Pt)
H H H C C H H H
H H C C H H
H H C C H H
H2
Pt
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Regents Question 01/03 26

• Which formula correctly represents the product
• of an addition reaction between ethene and
  chlorine?
• CH2Cl2
• (2) CH3Cl
• (3) C2H4Cl2
• (4) C2H3Cl

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49
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
H Cl H C C H H H
Cl2
UV
HCl
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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
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Regents Question 06/02 49
The process of joining many small molecules into
larger molecules is called (1) neutralization (2)
polymerization (3) Saponification (4)
substitution
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Regents Question 06/03 45
Which 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
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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
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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 pentanol Pentyl
propanoate water
Propanoic acid
1-Pentanol
H H O H C C C
OH H H
H H H H H HO C
C C C C H H H
H H H
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Making an ester by removing water from an acid
and an alcohol
Propanoic acid
1-Pentanol
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
Pentyl propanoate
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Name the ester
Methyl ethanoate
H O H H C C O C
H H H
Acid
Alcohol
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.
Alcohol will make you yl if you ate the acid.
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Regents Question 08/02 56
Given the ester ethyl butanoate a. Draw the
structural formula for this ester. b. Determine
the gram formula mass of this ester.
Even if you got the structure wrong but you got
the correct mass for the structure you drew, you
got one point.
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Amides (-CON) are made by reacting an organic
acid with ammonia or with an amine.
H O H C C N H H
H
H O H H C C N C
H H H H
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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 Pentyl
propanamide water
Propanoic acid
1-Pentanamine
H H O H C C C
OH H H
H H H H H H2N C
C C C C H H H
H H H
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Making an amide by removing water from an acid
and an amine
Propanoic acid
1-Pentanamine
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
Pentyl propanamide
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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.
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Proteins are polymers of amino
Remove water
O R HO C C N
H H H
O R HO C C N
H H
O R C C N H
H H
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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.

Enzyme
C6H12O6 2C2H5OH 2CO2
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Organic Reactions-Saponification

• Saponification is a reaction in which a lipid
  (fat or oil) is used to make soap.

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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
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Regents Question 08/02 21
In which reaction is soap a product? (1)
addition (2) substitution (3) Saponification (4)
polymerization
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