Organic Chemistry

Organic Chemistry I: Formulas, Names, and Properties
Chapter Goals
Saturated Hydrocarbons
1. Alkanes and Cycloalkanes 2. Naming Saturated Hydrocarbons
Unsaturated Hydrocarbons
3. Alkenes 4. Alkynes
Aromatic Hydrocarbons
5. Benzene 6. Other Aromatic Hydrocarbons 7. Hydrocarbons: A Summary
2
Chapter Goals
Functional Groups
8. 9. 10. 11. 12. 13. 14. 15. Organic Halides Alcohols and Phenols Ethers Aldehydes and Ketones Amines Carboxylic Acids Some Derivatives of Carboxylic Acids Summary of Functional Groups
3
Chapter Goals
Fundamental Classes of Organic Reactions
16. 17. 18. 19. Substitution Reactions Addition Reactions Elimination Reactions Polymerization Reactions
aturated !ydrocar"ons
# Hydrocarbons are chemical compounds that contain only C and H atoms. # Saturated hydrocarbons contain only single or sigma () bonds.
$ There are no double or triple bonds in these compounds.
# The primary source of hydrocarbons is petroleum and natural gas.
&l'anes and Cycloal'anes

# The simplest saturated hydrocarbons are called alkanes. # Methane, CH4, is the simplest alkane. # The alkanes form a homologous series.
$ Each member of the series differs by a specific number and kind of atoms.
! C ! ! ! or C!4
%

# The alkanes differ from each other by a CH 2 or methylene group. # All alkanes have this general formula.
CnH2n+2
# For example ethane, C2H6 , and propane, C3H8 , are the next two family members.

# Isomers are chemical compounds that have the same molecular formulas but different structures. Two alkanes have the molecular formula C 4H10.
They are a specific type of isomer called structural isomers.

Three alkanes have the formula C5H12.
There are three structural isomers of pentane.
!3C
!2 C
C !2
!2 C
C!3
n+pentane
*

!3C
!2 C
C !2
!2 C
C!3 C!3 C!3 C !3C ! C !2
n+pentane
2+methyl"utane
,-

,,

There are five isomeric hexanes, C6H14.
You draw them!
!2 C !2 C C!3
!3C
C !2
C !2
n+he.ane
,2

!3C
!2 C C !2 !2 C C !2 C!3 C!3 C !3C ! C !2 !2 C C!3
n+he.ane
2+methylpentane
,3

!3C
!2 C C !2 !2 C C !2 C!3 C!3 C !3C ! C !2 !2 C C!3 !2 !2 C ! C C!3 C !3C C!3 3+methylpentane
n+he.ane
2+methylpentane
,4

!3C
!2 C C !2 !2 C C !2 C!3 C!3 C !3C ! C !2 !2 C C!3 !2 !2 C ! C C!3 C !3C C!3 3+methylpentane
n+he.ane
C!3 C !2 C!3 C !3C C!3
2+methylpentane
2,2+dimethyl"utane
,5

!3C
!2 C C !2 !2 C C !2 C!3 C!3 C !3C ! C !2 C!3 C ! C!3 !3C ! C C!3 !2 C C!3 !2 !2 C ! C C!3 C !3C C!3 3+methylpentane
n+he.ane
C!3 C !2 C!3 C !3C C!3
2+methylpentane
2,2+dimethyl"utane
2,3+dimethyl"utane
,%

The number of structural isomers increases rapidly with increasing numbers of carbon atoms. The boiling points of the alkanes increase with molecular weight.
,(

Cyclic saturated hydrocarbons are called cycloalkanes.
They have the general formula CnH2n.
Some examples are:

!2C !2 C C!2
C C !2 !2 cyclopentane
,)

Some examples are:

!2C !2 C C!2 !2C !2C !2 C C !2 C!2 C!2
C C !2 !2 cyclopentane
cyclohe.ane
,*

Some examples are:
2-
Naming Saturated Hydrocarbons

The International Union of Pure and Applied Chemistry (IUPAC) names for the first 12 "straight-chain" or "normal" alkanes are given in this table.
Number of carbon atoms in chain , 2 3 4 5 % Name /ethane 0thane Propane 1utane Pentane !e.ane
2,

Number of carbon atoms in chain ( ) * ,,, ,2
Name !eptane Octane Nonane 2ecane 3nidecane 2odecane

22

Other organic compounds are named as derivatives of the alkanes. Branched-chain alkanes are named by the following rules. 1. Choose the longest continuous chain of carbon atoms which gives the basic name or stem.
23

2
Number each carbon atom in the basic chain, starting at the end that gives the lowest number to the first group attached to the main chain (substituent). For each substituent on the chain, we indicate the position in the chain (by an Arabic numeric prefix) and the kind of substituent (by its name).
The position of a substituent on the chain is indicated by the lowest number possible.
The number precedes the name of the substituent.

24

4 When there are two or more substituents of a given kind, use prefixes to indicate the number of substituents.
di = 2, tri = 3, tetra = 4, penta = 5, hexa = 6, hepta = 7, octa = 8, and so on.
5 The combined substituent numbers and names serve as a prefix for the basic hydrocarbon name. 6 Separate numbers from numbers by commas and numbers from words by hyphens.
Words are "run together".
25

Alkyl groups (represented by the symbol R) are common substituents. Alkyl groups are fragments of alkanes in which one H atom has been removed for the connection to the main chain. Alkyl groups have the general formula CnH2n+1. In alkyl groups the -ane suffix in the name of the parent alkane is replaced by -yl. A one carbon group is named methyl. A two carbon group is named ethyl. A three carbon group is named propyl.
2%
Unsaturated Hydrocarbons
The three classes of unsaturated hydrocarbons are: 1. alkenes and cycloalkenes, CnH2n 2. alkynes and cycloalkynes, CnH2n-2 3. aromatic hydrocarbons
2(
Alkenes
The simplest alkenes contain one C=C bond per molecule.
The general formula for simple alkenes is CnH2n.
The first two alkenes are:

ethene, C2H4
2)
Alkenes
The simplest alkenes contain one C=C bond per molecule.
The general formula for simple alkenes is CnH2n.
The first two alkenes are:

and propene, C3H6
2*
Alkenes
Each doubly bonded C atom is sp2 hybridized. The sp2 hybrid consists of:
two bonds (single bonds) and one and one bond (double bond)
3-
Alkenes
The systematic naming system for alkenes uses the same stems as alkanes. In the IUPAC system, the -ane suffix for alkanes is changed to -ene.
Common names for the alkenes have the same stem but use the suffix -ylene is used.
In chains of four or more C atoms, a numerical prefix shows the position of the lowest-numbered doubly bonded C atom.
Always choose the longest chain that contains the C=C bond.
3,
Alkenes
Polyenes contain two or more double bonds per molecule. Indicate the number of double bonds with suffixes:
-adiene for two double bonds. -atriene for three double bonds, etc.
The positions of the substituents are indicated as for alkanes. The position of the C=C bond(s) is/are given the lowest number(s) possible.
32
Alkenes
! ! C ! C C ! ! C ! C ! ! C ! !
,,3+he.adiene
33
Alkenes
! ! C ! C C ! ! C ! C ! ! C ! ! ! ! C ! C C ! ! C C ! ! C !
,,3+he.adiene ! ! ! C ! ! ! C ! C C C C C !
,,3,5+he.atriene
! ! C !
! 2,3+dimethyl+,,3,5+he.atriene
34
Cycloalkenes
Cycloalkenes have the general formula CnH2n-2. Examples are: cyclopentene
! C
C ! ! C C ! ! ! C
35
Cycloalkenes
cyclohexene
! ! C C C
C !
C ! C ! ! ! !
3%
Cycloalkenes
cycloheptene
! ! ! ! C C ! C ! C ! C ! C C ! ! ! !
3(
Alkynes
Alkynes contain CC bonds. The simplest alkyne is C2H2, ethyne, or acetylene. Alkynes with only one C C bond have the formula CnH2n-2. Each carbon atom in a C C bond is sp hybridized. Each sp hybrid contains two bonds and two bonds. The carbon atom will have one single bond and one triple bond.
3)
Alkynes
Alkynes are named like the alkenes except that the suffix -yne is used with the characteristic stem
The alkyne stem is derived from the name of the alkane with the same number of carbon atoms.
3*
Alkynes
Acetylene is an important industrial chemical.
It is prepared by the reaction of calcium carbide with water.
CaC2 ( s ) + H 2O( ) C2 H 2 ( g ) + CaO( s )
4-
Alkynes
Acetylene burns in a highly exothermic reaction
The combustion produces temperatures of about 3000C. Acetylene is used in cutting torches for welding.
2C2 H 2 ( g ) + 5O 2 ( g ) 4CO2 ( g ) + 2 H 2O( g )

Alkynes are very reactive
The two bonds are sights of special reactivity.
Addition reactions, such as hydrogenation, are common.
C2 H 2 ( g ) + 2H 2 ( g ) C2 H 6 ( g )
4,
!ydrocar"ons: & ummary

Carbon Atom Hybridization sp3 tetrahedral sp2 trigonal planar C uses 4 sp3 hy"rids 3 sp2 hy"rids 4 ,p or"ital C forms Example 4 "onds 3 "onds , "ond 2 "onds 2 "onds C!4
C2!4
sp linear
2 sp hy"rids 4 2 p or"itals
C2!2
42
Aromatic Hydrocarbons
Historically, aromatic was used to describe pleasant smelling substances. Now it refers to benzene, C6H6, and derivatives of benzene.
Other compounds that have similar chemical properties to benzene are also called aromatic.
43
Benzene
The structure of benzene, C6H6, is:
44
Other Aromatic Hydrocarbons

Coal tar is the common source of benzene and many other aromatic compounds. Some aromatic hydrocarbons that contain fused rings are: napthalene
45

phenanthrene
! ! ! ! C C C C ! ! C C C C C !
4%
C C C
C C !
! !

Many aromatic hydrocarbons contain alkyl groups attached to benzene rings (as well as to other aromatic rings). The positions of the substituents on benzene rings are indicated by the prefixes:
ortho meta para(o-) for substituents on adjacent C atoms (m-) for substituents on C atoms 1 and 3 (p-) for substituents on C atoms 1 and 4
4(
Functional Groups
Functional groups are groups of atoms that represent potential reaction sites. Compounds that contain a given functional group usually undergo similar reactions. Functional groups influence physical properties as well.
4)
Organic !alides
A halogen atom may replace almost any hydrogen atom in a hydrocarbon. The functional group is the halide (-X) group. Examples include:
chloroform, CHCl3
Cl Cl C ! Cl
4*
Organic !alides
1,2-dichloroethane, ClCH2CH2Cl
! Cl ! C C !
! ! C ! !
Cl !
5-
Organic !alides
para-dichlorobenzene
Cl
Cl
5,
Alcohols and Phenols

The functional group in alcohols and phenols is the hydroxyl (-OH) group. Alcohols and phenols can be considered derivatives of hydrocarbons in which one or more H atoms have been replaced by -OH groups. Phenols are derivatives of benzene in which one H has been replaced by replaced by -OH group.
52

Ethyl alcohol (ethanol), C2H5OH, is the most familiar alcohol.
53

Phenol, C6H5OH, is the most familiar phenol.
O!
54

Alcohols are considered neutral compounds because they are only very slightly acidic.
Alcohols can behave as acids but only in the presence of very strong bases.
Phenols are weakly acidic. Ka 1.0 x 10-10 for phenol Although phenols are very weakly acidic, they are also very corrosive.
55

Alcohols can be classified into three classes: 1. Primary (1) alcohols like ethanol have the -OH group attached to a C atom that has one bond to another C atom.
!3C C O! !2
5%

2. Secondary(2) alcohols have the OH group attached to a C atom that has bonds to 2 other C atoms. For example,2-propanol:
!3C !C O! !3C
5(

3. Tertiary (3) alcohols have the OH group attached to a C atom that is bonded to 3 other C atoms. For example, 2-methyl-2-propanol
O! !3C C C!3 C!3

5)

The stem for the parent hydrocarbon plus an -ol suffix is the systematic name for an alcohol. A numeric prefix indicates the position of the -OH group in alcohols with three or more C atoms. Common names are the name of the appropriate alkyl group plus alcohol.
5*

Alcohols are named using the stem for the parent hydrocarbon plus an -ol suffix in the systematic nomenclature. A numeric prefix indicates the position of the -OH group in alcohols with three or more C atoms. Common alcohol names are the name of the appropriate alkyl group plus the word alcohol.
!2 2 C
!2 ! 2 C C
O! O!
C!3 C! 3
!2C
O!
C !2 2
C C ! C ! !3 C C ! C 3 ! !2 2
! ! 2 2 C C
C! C! 3 3
!2 !2 C ! C !3C C C!3 O!
,+pentanol ,+pentanol alcohol ,+pentyl alcohol
2+pentanol 2+pentanol 2+pentyl 2+pentyl alcohol alcohol
3+pentanol 3+pentyl alcohol %-

There are several isomeric monohydric acyclic (contains no rings) alcohols that contain more than three C atoms. There are four isomeric four-carbon alcohols.
%,

!O
There are C! eight isomeric C five-carbon alcohols. C C C! ! C ! C ! ! O! You ! do it!

3
!2 C
!2 C
O!
!2 C
!2 !2 C ! C C!3 C !3C
,+pentanol
C!3
2+pentanol C!3
3+pentanol
C!3
!O
C!3 C C !C !2 !2
!3C
C!2 O! C!3
C ! C!3 !3C ! C O!
2+methyl+,+"utanol
C!3 C !3C ! C !2 !2 C
2+methyl+2+"utanol C!3!
3+methyl+2+"utanol
O!
!3C
C!3 O! 2,2+dimethyl+,+propanol
%2
3+methyl+,+"utanol

Polyhydric alcohols contain more than one -OH group per molecule.
O! C !2C ! C!2
O! !O
O!
O!
O!
O!
C ! C ! C!2 C ! C ! C !2 O! O! sor"itol
%3
glycerin

Phenols are usually called by their common (trivial) names.
O!
O! resorcinol
%4

O! O! C!3 O! resorcinol o+cresol
%5

O! O! C!3 O! resorcinol o+cresol C!3 m+cresol
%%
O!

O! O! C!3 O! resorcinol o+cresol C!3 m+cresol C!3 p+cresol
%(
O!
O!

Because the -OH group is quite polar, the properties of alcohols depend upon the number of -OH groups per molecule and the size of the organic group. The boiling points of monohydric alcohols increase with increasing molecular weight. The solubility of monohydric alcohols in water decrease with increasing molecular weight. Polyhydric alcohols are more soluble in water because of the two or more polar groups (-OH).
%)
Ethers
Ethers may be thought of as derivatives of water in which both H atoms have been replaced by alkyl or aryl groups.
! O !
5ater
%*
Ethers
! O ! !3C O !
5ater
an alcohol
(-
Ethers
! O ! !3C O ! !3C O C!3
5ater
an alcohol
an ether
(,
Ethers
Ethers are not very polar and not very reactive. They are excellent solvents. Common names are used for most ethers.
(2
&ldehydes and 6etones

The functional group in aldehydes and ketones is the carbonyl group.
O 7, 72 or !
car"onyl group
(3

Except for formaldehyde, aldehydes have one H atom and one organic group bonded to a carbonyl group.
(4

Ketones have two organic groups bonded to a carbonyl group.
(5

Common names for aldehydes are derived from the name of the acid with the same number of C atoms. IUPAC names are derived from the parent hydrocarbon name by replacing -e with -al.
!3C
C !2
!2 C
O C !2 C !
pentanal or pentyl aldehyde

(%

!3C
C !2
!2 C
O C !2 C !
!3C !3C C
O C C!3 !
2,3+dimethylproponal or 2,3+dimethylpropionaldehyde
((

!3C
C !2
!2 C
O C !2 C !
!3C !3C C
O C C!3 !
O C !
2,3+dimethylproponal or 2,3+dimethylpropionaldehyde
"en8anal or "en8yl aldehyde

()

The IUPAC name for a ketone is the characteristic stem for the parent hydrocarbon plus the suffix -one. A numeric prefix indicates the position of the carbonyl group in a chain or on a ring.
!3C
C !2
!2 C
O C !2 C C!3
2+he.anone or methyl pentyl 'etone

(*

!3C
C !2
!2 C
O C !2 C C!3 !3C
!2 C
O C !2 C C !2 C!3
3+he.anone or ethyl propyl 'etone

)-

!3C
C !2
!2 C
O C !2 C C!3 !3C
!2 C
O C !2 C C !2 C!3
C!3
3+he.anone or ethyl propyl 'etone
acetophenone or methyl phenyl 'etone

),

Many aldehydes and ketones occur in nature.
! !C C O C!3 O cinnamaldehyde testosterone
)2
C!
C!3 O!
Amines
Amines are derivatives of ammonia in which one or more H atoms have been replaced by organic groups (aliphatic or aromatic or a mixture of both). There are three classes of amines.
N !
ammonia
)3
Amines
!
N ! !
!3C
N !
ammonia
primary amine
)4
Amines
!
N ! !
!3C
N !
!3C
! C!3
ammonia
primary amine
secondary amine
)5
Amines
!
N ! !
!3C
N !
!3C
! C!3
!3C
C!3 C!3
ammonia
primary amine
secondary amine
tertiary amine
)%
&mines
Aniline is the simplest aromatic amine. It is much less basic than NH3. Aniline is a very important industrial chemical.
)(
&mines
Heterocylic amines have one or more N atoms in a ring structure. Many are important in living systems.
N pyridine
))
&mines
N N pyridine N pyrimidine
)*
&mines
N N pyridine N pyrimidine N N purine
*-
N N
Carboxylic Acids
Carboxylic acids contain the carboxyl functional group.
O O! The general formula for carboxylic acids is:

R represents an alkyl or an aryl group O
C 7,
O!
*,
Carboxylic Acids
IUPAC names for a carboxylic acid are derived from the name of the parent hydrocarbon. The final -e is dropped from the name of the parent hydrocarbon The suffix -oic is added followed by the word acid. Many organic acids are called by their common (trivial) names which are derived from Greek or Latin.
*2
Carboxylic Acids
Positions of substituents on carboxylic acid chains are indicated by numeric prefixes as in other compounds Begin the counting scheme from the carboxyl group carbon atom. They are also often indicated by lower case Greek letters.
= 1st C atom = 2nd C atom = 3rd C atom, etc.
*3
Carboxylic Acids
O !3C ! C C O! C!3 2+methylpropanoic acid or +methylpropanoic acid
*4
Carboxylic Acids
O !3C ! C C O! C!3
C!3
C C O! !3C ! C !2
2+methylpropanoic acid 3+methyl"utanoic acid or or +methylpropanoic acid +methyl"utanoic acid
*5
Carboxylic Acids
O !3C ! C C O! C!3
C!3
C C O! !3C ! C !2
O !2 !3C ! C C C C O! !2 C!3
2+methylpropanoic acid 3+methyl"utanoic acid or or +methylpropanoic acid +methyl"utanoic acid
4+methylpentanoic acid or +methylpentanoic acid
*%
Carboxylic Acids
Dicarboxylic acids contain two carboxyl groups per molecule.
O C C !O
O! O
o.alic acid
*(
Nomenclature of Carboxylic Acids

O C C !O O O! !O
O C C !2 O C O!
o.alic acid
malonic acid
*)
Nomenclature of Carboxylic Acids

O C C !O O O! !O
O C C !2 O C O! O C !2 C O!
!O
o.alic acid
malonic acid
O succinic acid
C !2
**
Carboxylic Acids
Aromatic acids are usually called by their common names. Sometimes, they are named as derivatives of benzoic acid which is considered to be the "parent" aromatic acid.
,--
Carboxylic Acids
!O O !O O
"en8oic acid
Cl p+chloro"en8oic acid
,-,
Carboxylic Acids
!O O !O O
"en8oic acid !O O
Cl p+chloro"en8oic acid O! O O!
C!3 p+toluic acid
O phthalic acid
,-2
Carboxylic Acids
Acid strengths of simple carboxylic acids vary little with chain length. However, substituents on a carbon atom in the chain can cause large variations in acid strengths .
,-3
Car"o.ylic &cids
Compound O ! C
O
Name 9ormic acid
6a ,:) . ,-+4
O!
!3C
O!
acetic acid
,:) . ,-+5
O !3C C !2 C
O!
propionic acid
,:4 . ,-+5
,-4
Car"o.ylic &cids
Compound O !3C
C O!
Name acetic acid
6a ,:) . ,-+5
O Cl C !2 C O! monochloroacetic acid ,:5 . ,-+3
O Cl ! C C O! Cl Cl Cl C O C Cl
,-5
dichloroacetic acid
5:- . ,-+2
O!
trichloroacetic acid
2:- . ,-+,
Carboxylic Acids
The -OH group in the carboxyl group of carboxylic acids, is displaced in many of their reactions. The non -OH portion of a carboxylic acid is called an acyl group.
O O!
7,
7,
car"o.yl group
acyl group
,-%
Some Derivatives of Carboxylic Acids

Four important classes of compounds contain acyl groups
They are all considered to be derivatives of carboxylic acids.
In these structures R's may represent either alkyl or aryl groups.
,-(

O O O C 7, O
7,
7,
Cl
acid anhydride
acid chloride
,-)

O O O C 7, O
7,
7,
Cl
acid anhydride
O
acid chloride
O
7,
72
7,
N!2
,-*
ester
amide

Acid anhydrides are related to their parent acids as follows:
The word anhydride means without water.
O 2 !3C C O! !3C
O O
O C!3
!2O
acetic acid
acetic anhydride
,,-

Acyl halides are much more reactive, and more volatile, than their parent acids. They react with water to form their parent acids and a hydrohalic acid.
O !3C C Cl
!2O
!3C
O!
!Cl
acetyl chloride
acetic acid
,,,

Acyl halides are prepared by reacting their parent acids with PCl3, PCl5, or SOCl2. The more volatile acid halide is then distilled out of the reaction mixture.
!O O Cl O
;
"en8oic acid
PCl5
"en8oyl chloride
,,2

Esters are prepared by heating a carboxylic acid with an alcohol in the presence of a small amount of an inorganic acid.
The reaction mixture will contain some ester and water, as well as unreacted acid and alcohol.
O
!3C
O!
!3C
C !2
O!
!2 O4 !3C
O C O
!2 C
C!3
!2O
ethanoic acid or acetic acid
ethanol or ethyl alcohol
ethyl ethanoate or ethyl acetate
,,3

Esters are usually called by their common names. Many simple esters occur naturally and have pleasant odors.
Esters are frequently used in fragrances and as artificial flavors.
!3C !2 C
O !2 C O C!3 !2 C !2 C !2 C !2 C
C !2
!3C
C !2
C !2
C !2
C!3
ethyl "utanoate or ethyl "utyrate odor o9 pineapples
octyl ethanoate or octyl acetate odor o9 oranges

,,4

Fats are solid esters of glycerol and (mostly) saturated acids at room temperature. Oils are liquid esters of glycerol and primarily unsaturated acids at room temperature. The "acid" parts of fats and oils usually contain even numbers of C atoms in naturally occurring fats and oils. 16 and 18 carbon chains are the most commonly found chain sizes in nature.
,,5

Some acids that are found (as their esters) in fats and oils include:
!3C
!2 C C !2 !2 C C !2 !2 C C !2 !2 C C !2 !2 C C !2 !2 C C !2 !2 C O C !2 C O!
palmitic acid C!3<C!2=,4COO!

,,%

Stearic acid is often found in beef fat.
!2 C !2 C !2 C !2 C !2 C !2 C !2 C !2 C O C !2 C O!
!3C
C !2
C !2
C !2
C !2
C !2
C !2
C !2
stearic acid C!3<C!2=,%COO!
,,(

Triglycerides are the triesters of glycerol. The common name for triglycerides is tri (acid stem) plus an -in suffix.
For example, tripalmitin.
,,)

Waxes are esters of long chain fatty acids and alcohols other than glycerol. Commonly, waxes are derived from monohydric alcohols. Beeswax and carnauba wax are esters of myricyl alcohol, C30H61OH.
,,*

Carnauba wax is often used in car waxes.
O C25!5, C O C3-!%,
carnau"a 5a.
,2-

Dihydric alcohols (2 OHs per molecule) can react with dicarboxylic acids (2 COOHs per molecule) to form polyesters. Ester linkages are formed at both ends of both molecules to give polymeric esters with very high molecular weights.
O C !O terephthalic acid dicar"o.ylic acid C O O! !2 !2 C C !O O! ethylene glycol dihydric alcohol
,2,

> O > O C !2C C O dacron
,22
O C!2

Amides are derivatives of organic acids and primary or secondary amines. The functional groups of amides are:
O 7, C N ! ! or 7, O C N ! 72 or 7, O C N 73 72
,23

Amides are also named as derivatives of carboxylic acids. The suffix -amide is substituted for -ic acid or -oic acid.
O !3C C N ! ethanamide or acetamide "en8amide ! O C N!2
,24

When an aryl or alkyl substituent is present on the N atom, the letter N and the name of the substituent are prefixed to the name of the unsubstituted amide.
!2C O !3C C N ! N+ethylethanamide or N+ethylacetamide N+ethyl+N+methyl"en8amide C!3 O C N C!3 C!3
,25

Acetaminophen Tylenol - is an amide.
,2%
ummary o9 the Functional Groups

A summary of the functional groups is:
,2(
,2)
Substitution Reactions
In a substitution reaction an atom or group of atoms attached to a carbon atom is replaced (substituted for) by another atom or group of atoms. There is no change in the degree of saturation at the reactive carbon atom. Halogenation reactions are an important class of substitution reactions. Chlorine reacts with alkanes in free radical chain reactions (also substitution reactions).
,2*
u"stitution 7eactions
Free radical chain reactions
The halogenation of methane is one example.
@@ @@ @ @ Cl @ @ Cl @ @@ @@ @
heat or u? light
@@ : 2 @ Cl @ @@ 9ree radicals
,3-
@@ @@ @ @ Cl @ @ Cl @ @@ @@ @ heat or u? light @@ : 2 @ @ Cl @@ 9ree radicals
! @@ @ !@ C@ @! @@ !
@@ : @ @ Cl @@
! @@ : @ !@C ; @@ ! methyl radical
@@ @ @ Cl @ @! @@
,3,
@@ @@ @ @ Cl @ @ Cl @ @@ @@ @ heat or u? light @@ : 2 @ Cl @ @@ 9ree radicals ! @@ : !@ C ; @ @@ ! methyl radical
! @@ !@ C @ @ @! @@ !
@@ : @ Cl @ @@
@@ @ @ Cl @ @! @@
! @@ : !@ C @ @@ !
@@ @@ @ @ Cl @ @ Cl @ @@ @@ @
! @@ @@ !@ C @ @ @ Cl @ @ @@ @@ ! methyl chloride
@@ : @ @ Cl @@
,32
Free radical chain reactions
Many substitution reactions of alkanes produce more than one product.
! ! C Cl ! !
Cl
Cl
Cl
C Cl !
!Cl
,33
! ! C Cl ! ! Cl C Cl ! !
Cl
Cl
Cl
C Cl ! !
!Cl
Cl
Cl
Cl
C Cl Cl
!Cl
,34
! ! C ! ! Cl C ! ! Cl C Cl Cl Cl Cl !
; ; ;
Cl
Cl
Cl
C ! !
Cl
; ; ;
!Cl
Cl
Cl
Cl
C Cl Cl
Cl
!Cl
Cl
Cl
Cl
C Cl
Cl
!Cl
,35
Substitution Reactions
Nitration reaction of an aromatic hydrocarbon replaces an H atom attached to an aromatic ring with a nitro, -NO2, group.
NO !2 O4 2
!NO
,3%
Addition Reactions
An addition reaction involves an increase in the number of groups attached to carbon.
The degree of saturation of the molecule is increased.
! C C !
! !
;
!
Cl
! C C ! Cl Cl
,3(
Addition Reactions
Hydrogenation is a very important kind of addition reaction.
Hydrogenation is used to convert unsaturated fats and oils to saturated fats or oils.
! C C !
! !
;
!
! 2
! C C ! ! !
,3)
Elimination Reactions
An elimination reaction involves the removal of groups attached to carbon.
The degree of unsaturation increases.
1r 1r !C C! C!3 !3C ! C C ! ! C!3 C C
An in
acetic acid ! C C!3 ! !3C 3 or ethanol mi.ture o9 cis 4 trans+2+"utene
An1r
,3*
Elimination Reactions
Dehydration is an important kind of elimination reaction.
! O! ! ! concentrated !C C! C C ! ! O4 ! ! ! 2
!2O
,4-
Polymerization Reactions
A polymer is a large molecule that consists of a high-molecular weight chain of small molecules.
The small molecules that have been joined to form the polymer are called monomers.
Synthetic polymers are a relatively new class of molecules.

The first one, bakelite, was discovered in 1909. Nylon, which is still extensively used, was discovered in 1930s.
,4,
Addition polymerization is a large commercial process in the United States. Polyethylene is the addition polymer made in the largest quantities in the United States.
Polyethylene is used to make Coke bottles, plastic bags, etc.
,42
Addition polymerization
Polyethylene formation
n !2C C!2 ethylene
catalyst >
C!2
C!2
>
polyethylene
,43
Addition polymerization
Teflon is the material used in nonstick frying pans and other kitchen utensils.
F n F C C
F F
catalyst heat
F > C
F C
n
>
tetra9luoroethylene
F F polytetra9luoroethylene or Be9lon
,44
Formation of rubber
Natural rubber is a polymer made of isoprene (2-methyl-1,3-butadiene) units that form a unique stereoisomeric structure.
!3C 2n !2C
! C C C!2
>
C!3 C!3 ! 2 C!2 C C C C!2 C! C!2 C!

natural ru""er
>
isoprene
,45
Vulcanization of rubber
Natural rubber is a sticky, soft compound when heated which limited its commercial potential.
Charles Goodyear discovered in 1839 that heating rubber with sulfur removed the stickiness and made the substance elastic.
This is the basis of modern tire production.
Vulcanization provides disulfide cross-linking bonds between the isoprene units.

,4%
Copolymers
If two different monomers are mixed and the polymerized, copolymers are formed.
Styrene butadiene rubber - SBR - is an important copolymer used in tire production.
,4(
Copolymers
! ! 3 C C !
! C C ! ! !
"utadiene
styrene
,4)
! > ! C C!2 C !2C ! C!2 C !2 C C !
C!2 C !
>
C C C !2 C!2 ! !
tyrene + "utadiene ru""er < 17=

,4*
Condensation Polymers
Condensation polymers occur when two molecules react and eliminate a small molecule. Molecules eliminated commonly are water and HCl.
Important condensation polymers include nylon, dacron, and kevlar.

Dacron is used in clothing to make it wrinkle free. Blood does not clot in contact with dacron thus it is used in artificial arteries.
,5-
Dacron formation
!O C O
!2 !2 C C O! !O
;
O O!
ethylene glycol
terephthalic acid
,5,
O ! O C C O !2 !2 C
O C O C C O !2 !2
n
!2O
2acron is a polyester
,52
Condensation Polymers Nylon was first made by Wallace Carothers in the 1930s.
Nylon is widely used in a variety of commercial products including stockings, rope, guitar strings, fire-proof clothing.
,53
Nylon 66 formation
O !2 C !2 C !2 C !2 C !2 C
!O
C !2
C !2
C O
O!
!2N
C !2
C !2
C !2
N!2
adipic acid
he.amethylene diamine
,54
!2N
C !2
!2 C
C !2
!2 C
C O
! N
C !2
!2 C
C !2
!2 C
C !2
!2 C
O N !
n
O!
!2O
Nylon is a polyamide
,55

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Organic Chemistry I: Formulas, Names, and Properties

# The primary source of hydrocarbons is petroleum and natural gas.

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

C!3 C!3 C!3 C !3C ! C !2

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

&l'anes and Cycloal'anes

Some examples are:

&l'anes and Cycloal'anes

Some examples are:

&l'anes and Cycloal'anes

Some examples are:

Naming Saturated Hydrocarbons

Naming Saturated Hydrocarbons

Name !eptane Octane Nonane 2ecane 3nidecane 2odecane

Naming Saturated Hydrocarbons

Naming Saturated Hydrocarbons

The number precedes the name of the substituent.

Naming Saturated Hydrocarbons

Naming Saturated Hydrocarbons

The first two alkenes are:

The first two alkenes are:

CaC2 ( s ) + H 2O( ) C2 H 2 ( g ) + CaO( s )

2C2 H 2 ( g ) + 5O 2 ( g ) 4CO2 ( g ) + 2 H 2O( g )

Addition reactions, such as hydrogenation, are common.

!ydrocar"ons: & ummary

Other Aromatic Hydrocarbons

Other Aromatic Hydrocarbons

Other Aromatic Hydrocarbons

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

O! !3C C C!3 C!3

Alcohols and Phenols

Alcohols and Phenols

,+pentanol ,+pentanol alcohol ,+pentyl alcohol

2+pentanol 2+pentanol 2+pentyl 2+pentyl alcohol alcohol

3+pentanol 3+pentyl alcohol %-

Alcohols and Phenols

Alcohols and Phenols

There are C! eight isomeric C five-carbon alcohols. C C C! ! C ! C ! ! O! You ! do it!

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

Alcohols and Phenols

&ldehydes and 6etones

&ldehydes and 6etones

&ldehydes and 6etones

&ldehydes and 6etones