Organic Chemistry Chapter on Structure and Properties of Carbon Compounds

Chemistry: A Molecular Approach, 1st Ed.
Nivaldo Tro
Chapter 20 Organic Chemistry

Roy Kennedy Massachusetts Bay Community College Wellesley Hills, MA
2008, Prentice Hall
Structure Determines Properties

Organic compounds all contain carbon
CO, CO2 , carbonates and carbides are inorganic other common elements are H, O, N, (P, S)
Carbon has versatile bonding patterns

chains, rings, multiple bonds chain length nearly limitless
Carbon compounds generally covalent

molecular; gases, liquids, or low melting solids; varying solubilities; nonconductive in liquid
C - C bonds unreactive (very stable)

Tro, Chemistry: A Molecular Approach 2
Bond Energies and Reactivities

C-C S-S Si-Si N-N O-O 347 kJ H3C-CH3 214 kJ 213 kJ 159 kJ 138 kJ HS-SH
H3Si-SiH
NONREACTIVE IN AIR EXTREMELY REACTIVE
SPONTANEOUS 3 BURNS IN AIR EXTREMELY REACTIVE REACTIVE
H2N-NH2
HO-OH
Tro, Chemistry: A Molecular Approach
Allotropes of Carbon - Diamond
Allotropes of Carbon - Graphite
Carbon Bonding
mainly forms covalent bonds C is most stable when it has 4 single covalent bonds,
but does form double and triple bonds
C=C and CC are more reactive than CC C with 4 single bonds is tetrahedral, 2 singles and 1 double is trigonal planar 2 doubles or 1 triple and 1 single is linear
Hydrocarbons
hydrocarbons contain only C and H
aliphatic or aromatic
insoluble in water
no polar bonds to attract water molecules
aliphatic hydrocarbons
saturated or unsaturated aliphatics
saturated = alkanes, unsaturated = alkenes or alkynes
may be chains or rings chains may be straight or branched
aromatic hydrocarbons
Uses of Hydrocarbons
Number of C atoms State Major Uses
1-4
5-7 6-18 12-24 18-50
heating and gas cooking fuel liquids, solvents, (low boiling) gasoline liquids gasoline jet fuel; camp liquids stove fuel diesel fuel, liquids, lubricants, (high boiling) heating oil petroleum jelly, solids paraffin wax
50+
Saturated Hydrocarbons
a saturated hydrocarbon has all C-C single
bonds
it is saturated with hydrogens
saturated aliphatic hydrocarbons are called

alkanes chain alkanes have the general formula CnH2n+2
Unsaturated Hydrocarbons
unsaturated hydrocarbons have one of more C=C
double bonds or CC triple bonds unsaturated aliphatic hydrocarbons that contain C=C are called alkenes
the general formula of a monounsaturated chain alkene is CnH2n remove 2 more H for each additional unsaturation
unsaturated aliphatic hydrocarbons that contain CC

are called alkynes
the general formula of a monounsaturated chain alkyne is CnH2n-2 remove 4 more H for each additional unsaturation
Unsaturated Hydrocarbons
H3C H C
CH3
C H
CH3
H3C
CH3
HC H2C
H C
CH2 CH2
CH3 H2 C C CH2 C H2
C H2 C H2
H3C
CH3
H2C H2C
H2 C C
H2 C CH2
H2C
H2 C
H2C C H2
CH2
11
Aromatic Hydrocarbons
contain benzene ring structure even though they are often drawn with C=C,
they do not behave like alkenes
12
H2 C C H C 2 CH 3 H3C C C CH 3 H H CH3 C C 2C CH CH3 2 C H3C H3C C H H C 2 CH 3 C H2
H2 C C
CH HC CH 22 H2C H H2 C CH2 2 CH C C 2 C H2 H2
H C C2 H
H2 C
alkanes alkenes alkynes

14
Formulas
molecular formulas just tell you what
kinds of atoms are in the molecule, but they dont tell you how they are attached structural formulas show you the attachment pattern in the molecule models not only show you the attachment pattern, but give you an idea about the shape of the molecule
15
Condensed Structural Formulas

attached atoms listed in order
central atom with attached atoms
follow normal bonding patterns

use to determine position of multiple bonds
() used to indicate more than 1 identical

group attached to same previous central atom
unless () group listed first in which case attached to next central atom
Line-Angle Formulas
each angle, and beginning and end represent a C
atom H omitted on C
included on functional groups
multiple bonds indicated

double line is double bond, triple line is triple bond
17
Formulas
18
Formulas
H CH4 H C H H C2H6 CH3CH3 H C H H C3H8 CH3CH2CH3 H C H H C4H10 CH3CH2CH2CH3 H C H H C4H10 C(CH3)2 H C H H
H C H H C H H C H H C C H H C H H C H H C H H
19
H C H H
Isomers = different molecules with the same
Isomerism
molecular formula Structural Isomers = different pattern of atom attachment

Constitutional Isomers
Stereoisomers = same atom attachments, different

spatial orientation
20
H H C
H H
H H H H H H H Butane, BP = 0C
C H C
H H H H H H H H
C C C H H C C C Structural Isomers of C4H10

H H
H CH C C C H H
H H H H H Isobutane, BP = -12C H C H C C C HH H H H C C H C H H H H H H C H H C H
H
H
21
Rotation about a bond is not isomerism
22
Possible Structural Isomers

Carbon Molecular Possible Content Formula Isomers 4 C4H10 2 5 C5H12 3 6 C6H14 5 7 C7H16 9 8 C8H18 18 9 C9H20 35 10 C10H22 75
Ex 20.1 Write the structural formula and carbon skeleton formula for C6H14
start by connecting the carbons in a line
determine the C skeleton of the other isomers
C C C C C C C C C C C C C C C
C C C C C C C C
fill in the H to give each C 4 bonds
H H C H H C H H
H H H H C C C H
H H
H H
H C C C C C H
H H
C C C C H
H H H
H H C H H H C H H
H H
C H C C
H H
C
H H
C H C C
H C H C H
C H H C H
H
H C H C H C C C C H C H C H
H H
H H
C CC C
C C C C
H H H
C C H H H C H H C H H H
convert each to a carbon skeleton formula each bend and the ends represent C atoms
H H C H
H H C H H H C C H
H H H C H H
H H C C
H H C C
H C H
H H C H H H C C H H C H H H C H H
H H
H H
H C H H
H C C C H
H C H
H C H H
H
C H
H H H C C H
H H C
H C
H C
H C H
H H H
H H H C H H C H H H
Stereoisomers
stereoisomers are different molecules whose
atoms are connected in the same order, but have a different spatial direction optical isomers are molecules that are nonsuperimposable mirror images of each other geometric isomers are stereoisomers that are not optical isomers
Nonsuperimposable Mirror Images
mirror image cannot be rotated so all its atoms align with the same atoms of the original molecule
Chirality
any molecule with a nonsuperimposable mirror
image is said to be chiral any carbon with 4 different substituents will be a chiral center a pair of nonsuperimposable mirror images are called a pair of enantiomers
29
Optical Isomers of 3-methylhexane
30
Plane Polarized Light

light that has been filtered so that only those
waves traveling in a single plane are allowed through
31
a pair of enantiomers have all the same physical
Optical Activity
properties except one the direction they rotate the plane of plane polarized light
each will rotate the plane the same amount, but in opposite directions dextrorotatory = rotate to the right levorotatory = rotate to the left
an equimolar mixture of the pair is called a racemic

mixture
rotations cancel, so no net rotation
32
Chemical Behavior of Enantiomers

a pair of enantiomers will have the same
chemical reactivity in a non-chiral environment but in a chiral environment they may exhibit different behaviors
enzyme selection of one enantiomer of a pair
33
Alkanes
aka paraffins aliphatic general formula CnH2n+2 for chains very unreactive come in chains or/and rings
CH3 groups at ends of chains, CH2 groups in the middle chains may be straight or branched
saturated branched or unbranched

Name Methane Ethane Propane Butane Pentane Hexane
Lewis Structure
H C H H H
Formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH3
Boiling Point -162C -89C -42C 0C 36C 69C

35
H H
H H C
H H C H
H H C H
H H C H
H C H H
H C
H C H
C H
H C
H C H
H C H
H C H H C H
H C H H
H C H
H C H
H C H
H C H
H C H
H C H H
Naming
each name consists of 3 parts
prefix
indicates position, number, and type of branches indicates position, number, and type of each functional group
parent
indicates the length of the longest carbon chain or ring
suffix
indicates the type of hydrocarbon
ane, ene, yne
certain functional groups

Naming Alkanes
1) Find the longest continuous carbon chain 2) Number the chain from end closest to a branch if first branches equal distance use next in 3) Name branches as alkyl groups locate each branch by preceding its name with the carbon number on the chain 4) List branches alphabetically do not count n-, sec-, t-, count iso 5) Use prefix if more than one of same group present di, tri, tetra, penta, hexa do not count in alphabetizing
37
Alkyl Groups
H H C H CH3-, METHYL
H H H C C H H
H H H H C C C H H H H CH3 H C C H H
CH3CH2-, ETHYL
CH3CH2CH2-, PROPYL
(CH3)2CH-, ISOPROPYL
38
More Alkyl Groups

H H H H H C C C C H H H H
H H CH3 H C C C H H H H H C H CH3 H C C H H C H 3 C H 2 C H 2 C H 2 -, n - B U T Y L
CH3CH2(CH3)CH-, sec-BUTYL
(CH3)2CHCH2-, ISOBUTYL
CH3 H 3C C CH3
(CH3)3C-, tert- B U TYL

39
Examples of Naming Alkanes

H H C H C H C H H C H H
2-methylpentane
C H
CH3 H
H 3-isopropyl-2,2-dimethylhexane H C H
CH3 H C C
H C H
H C H
H C H H
CH3 CH
CH3 CH3
Example Name the alkane

CH3CHCH2CHCH3 CH3 CH3
1) find the longest continuous C chain and use it

to determine the base name
since the longest chain has 5 C the base name is pentane


2) identify the substituent branches

there are 2 substituents both are 1 C chains, called methyl

3) number the chain from the end closest to a
substituent branch
if first substituents equidistant from end, go to next substituent in
then assign numbers to each substituent based on the number of the main chain C its attached to
both substituents are equidistant from the end
CH3CHCH2CHCH3 CH3
2
CH3
4
43

4) write the name in the following order
1) substituent number of first alphabetical substituent followed by dash 2) substituent name of first alphabetical substituent followed by dash if its the last substituent listed, no dash use prefixes to indicate multiple identical substituents 3) repeat for other substituents alphabetically 4) name of main chain
CH3CHCH2CHCH3 CH3
2
2,4 dimethyl pentane
CH3
4
44
Practice Name the Following

CH3 CH3 CHCHCH2CH3 CH2 CH3
45

CH3 CH3 CHCHCH2CH3 CH2 CH3
3-ethyl-2-methylpentane
46
Drawing Structural Formulas

draw and number the
base chain carbon skeleton add the carbon skeletons of each substituent on the appropriate main chain C add in required Hs 4-ethyl-2-methylhexane
C C C C C C 1 2 3 4 5 6
C C C C C C C C C
CH3 CH CH2 CH CH2 CH3 CH3 H2C CH3

47
Practice Draw the structural formula of 4isopropyl-2-methylheptane
48
Practice Draw the structural formula of 4isopropyl-2-methylheptane

CH3 CH CH2 CH CH2 CH2 CH3 CH3 HC CH3 CH3
49
Alkenes
also known as olefins aliphatic, unsaturated formula for one double bond = CnH2n
C=C double bonds
subtract 2 H from alkane for each double bond flat
trigonal shape around C
much more reactive than alkanes polyunsaturated = many double bonds

51
Alkenes
ethene = ethylene
H C C H H
H
propene
H C C CH3 H
52
Physical Properties of Alkenes

Name ethene propene 1-butene 1-pentene 1-hexene 1-heptene 1-octene 1-nonene 1-decene Formula CH2=CH2 CH2=CHCH3 CH2=CHCH2CH3 CH2=CH(CH2)2CH3 CH2=CH(CH2)3CH3 CH2=CH(CH2)4CH3 CH2=CH(CH2)5CH3 CH2=CH(CH2)6CH3 CH2=CH(CH2)7CH3 Molar Mass BP, C Density, g/cm 3 28 -104 0.52 42 56 70 84 98 112 126 140 -47 -6 30 64 93 122 146 171 0.59 0.59 0.64 0.68 0.70 0.72 0.73 0.74
53
Alkynes

also known as acetylenes aliphatic, unsaturated CC triple bond formula for one triple bond = CnH2n-2
subtract 4 H from alkane for each triple bond
linear shape more reactive than alkenes

55
Alkynes
ethyne = acetylene
H C C H
propyne
H C C CH3
56
Physical Properties of Alkynes

Name ethyne propyne 1-butyne 1-pentyne 1-hexyne 1-heptyne 1-octyne 1-nonyne 1-decyne Formula CHCH CHCCH3 CHCCH2CH3 CHC(CH2)2CH3 CHC(CH2)3CH3 CHC(CH2)4CH3 CHC(CH2)5CH3 CHC(CH2)6CH3 CHC(CH2)7CH3 Molar Mass BP, C Density, g/cm 3 28 42 56 70 84 98 112 126 140 -104 -47 -6 30 64 93 122 146 171 0.52 0.59 0.59 0.64 0.68 0.70 0.72 0.73 0.74
57
Naming Alkenes and Alkynes

change suffix on main name from -ane to -ene
for base name of alkene, or to -yne for the base name of the alkyne number chain from end closest to multiple bond number in front of main name indicates first carbon of multiple bond
58
Examples of Naming Alkenes

H H C H H C H H
2-methyl-1-pentene
C H
CH3 H
H 3-isopropyl-2,2-dimethyl-3-hexene H C H
CH3 C C C H
H C H
H C H H
CH3 CH
CH3 CH3
Examples of Naming Alkynes

H H C H C H H
3-methyl-1-pentyne
CH3 H
H 4-isopropyl-5,5-dimethyl-2-hexyne H C H
CH3 H C C C C
H C H H
CH3 CH CH3 CH3
60
Name the Alkene

1) find the longest, continuous C chain that
contains the double bond and use it to determine the base name H2 C CH3
H3 C CH C CH CH3 H2 C CH3
since the longest chain with the double bond has 6 C the base name is hexene
Name the Alkene

H2 C CH3 H3 C CH C CH CH3 H2 C CH3
there are 2 substituents one is a 1 C chain, called methyl the other one is a 2 C chain, called ethyl
Name the Alkene

3) number the chain from the end closest to the
double bond then assign numbers to each substituent based on the number of the main chain C its attached to
3 4
H2 C CH3
4
H3 C CH
5 6
C CH CH3
3 2 1
H2 C CH3
63
Name the Alkene

1) substituent number of first alphabetical substituent substituent name of first alphabetical substituent use prefixes to indicate multiple identical substituents 2) repeat for other substituents 3) number of first C in double bond name of main chain 3
H3 C CH
4 5 6
H2 C CH3
3 2 1
3ethyl 4methyl2hexene
C CH CH3
H2 C CH3

CH3 H3C C C CH2 CH3 H2C CH3
65

CH3 H3C 3C H2C
2
CH C CH 3 2 4
5 6
CH3
1
3,4-dimethyl-3-hexene
66
Name the Alkyne

1) find the longest, continuous C chain that
contains the triple bond and use it to determine the base name
CH3 CH CH2 CH C CH3 HC CH3 CH3
CH3
since the longest chain with the triple bond has 7 C the base name is heptyne
Name the Alkyne

CH3 CH CH2 CH C CH3 HC CH3
there are 2 substituents one is a 1 C chain, called methyl the other one is called isopropyl
CH3
CH3
Name the Alkyne

3) number the chain from the end closest to the
triple bond then assign numbers to each substituent based on the number of the main chain C its attached to
CH3 CH CH2 CH C 7 6 5 4 3
6 CH3
C
2
CH3
1
HC
CH3
CH3
69
Name the Alkyne

1) substituent number of first alphabetical substituent substituent name of first alphabetical substituent use prefixes to indicate multiple identical substituents 2) repeat for other substituents 3) number of first C in double bond name of main chain
CH3 CH CH2 CH C 7 6 5 4 3
6 CH3
C
2
CH3
1
HC
CH3
4isopropyl 6methyl2heptyne
70
CH3

CH3 H 3C C C CH CH2CH3
71

CH3 H 3C C
4 3
C
2 5
CH
1
CH2CH3
3,3-dimethyl-1-pentyne
72
Geometric Isomerism
because the rotation around a double bond is highly
restricted, you will have different molecules if groups have different spatial orientation about the double bond this is often called cis-trans isomerism when groups on the doubly bonded carbons are cis, they are on the same side when groups on the doubly bonded carbons are trans, they are on opposite sides
73
Free Rotation Around CC
74
Cis-Trans Isomerism
75
Reactions of Hydrocarbons
all hydrocarbons undergo combustion combustion is always exothermic
about 90% of U.S. energy generated by combustion
2 CH3CH2CH2CH3(g) + 13 O2(g) 8 CO2(g) + 10 H2O(g) CH3CH=CHCH3(g) + 6 O2(g) 4 CO2(g) + 4 H2O(g) 2 CH3CCCH3(g) + 11 O2(g) 8 CO2(g) + 6 H2O(g)
76
Other Alkane Reactions

Substitution
replace H with a halogen atom initiated by addition of energy in the form of heat or ultraviolet light
to start breaking bonds
generally get multiple products with multiple substitutions

H H H C C H + Cl Cl H H
heat or UV light
H Cl H C C H + H Cl H H
77
Other Alkene and Alkyne Reactions

Addition reactions
adding a molecule across the multiple bond
Hydrogenation = adding H2
converts unsaturated molecule to saturated alkene or alkyne + H2 alkane
Halogenation = adding X2 Hydrohalogenation = adding HX

HX is polar when adding a polar reagent to a double or triple bond, the positive part attaches to the carbon with the most Hs
78
Addition Reactions
H H C C H H C C C H H H CH CH CH 3 3 3 + H-Cl Cl H ++
22
H Cl H C C H H H H
H H C C
CH CH 33 3
Cl Cl H
79
Aromatic Hydrocarbons
contain benzene ring structure even though they are often drawn with C=C,
they do not behave like alkenes
80
Resonance Hybrid
the true structure of benzene is a resonance
hybrid of two structures
81
Naming Monosubstituted Benzene Derivatives

(name of substituent)benzene
halogen substituent = change ending to o
F
CH2CH2CH3
fluorobenzene
propylbenzene
or name of a common derivative

CH3 NH2 OH HC CH2
toluene
aniline
phenol
styrene
82
Naming Benzene as a Substituent

when the benzene ring is not the base name, it is
called a phenyl group
H2C CH CH2
CH CH2
CH3
4-phenyl-1-hexene
Naming Disubstituted Benzene Derivatives

number the ring starting at attachment for first
substituent, then move toward second
order substituents alphabetically use di if both substituents the same
F
3 2
CH3
1 2
CH3
1 Br 1-bromo-3-fluorobenzene
1,2-dimethylbenzene
84
Naming Disubstituted Benzene Derivatives

alternatively, use relative position prefix
ortho- = 1,2; meta- = 1,3; para- = 1,4
CH3 Cl
CH3
CH3
Cl
Cl
2-chlorotoluene ortho-chlorotoluene o-chlorotoluene

3-chlorotoluene meta-chlorotoluene m-chlorotoluene
4-chlorotoluene para-chlorotoluene p-chlorotoluene

85

F
Br
Br
Cl
86

F
Br
Br
Cl
1-chloro-4-fluorobenzene
1,3-dibromobenzene or meta-dibromobenzene or m-dibromobenzene

87
Polycyclic Aromatic Hydrocarbons

contain multiple benzene rings fused together
fusing = sharing a common bond
88
Reactions of Aromatic Hydrocarbons

most commonly, aromatic hydrocarbons
undergo substitution reactions replacing H with another atom or group
89
Functional Groups
other organic compounds are hydrocarbons in which
functional groups have been substituted for hydrogens a functional group is a group of atoms that show a characteristic influence on the properties of the molecule
generally, the reactions that a compound will perform are determined by what functional groups it has since the kind of hydrocarbon chain is irrelevant to the reactions, it may be indicated by the general symbol R
R group
CH3OH
functional group
90
91
R-OH ethanol = CH3CH2OH

gasohol
Alcohols
grain alcohol = fermentation of sugars alcoholic beverages

proof number = 2X percentage of alcohol
isopropyl alcohol = (CH3)2CHOH
methanol = CH3OH
2-propanol rubbing alcohol poisonous
wood alcohol = thermolysis of wood paint solvent poisonous

92
Naming Alcohols
main chain contain OH number main chain from end closest to OH give base name ol ending and place number of C
on chain where OH attached in front name as hydroxy group if other higher precedence group present
1 CH3 2CH2
OH CH3 3 CH 4 C 5 CH 6 CH2 CH2CH3
4-ethyl-4-methyl-3-hex-5-enol
Reactions of Alcohols
Nucleophilic Substitution
CH3
CH3 CH3
OH + HCl CH3Cl + H2O

Acid Catalyzed Elimination (Dehydration)
CH2OH CH2 CH2 + H2O

H2SO4
Oxidation
CH2OH CH3
CH3 OH
-2H
CHO CH3
-2H
COOH
with Reactive Metals
+ Na CH3ONa+ + H2
94
Aldehydes and Ketones

contain the carbonyl group aldehydes = at least 1 side H ketones = both sides R groups many aldehydes and ketones have pleasant tastes and aromas some are pheromones formaldehyde = H2C=O
pungent gas formalin = a preservative wood smoke, carcinogenic nail-polish remover
O C
formaldehyde
acetone = CH3C(=O)CH3
acetone
95
Aldehyde Odors and Flavors

butanal = butter
O C H
O O H HO
CH2CH2CH3
vanillin = vanilla
HO
benzaldehyde = almonds
O C H
cinnamaldehyde = cinnamon
H C C H O C H
96
Ketone Odors and Flavors

acetophenone = pistachio
O H3C C
carvone = spearmint
H3C CH2 O C CH3
ionone = raspberries
H3C CH3 O H C C C CH3 H
muscone = musk
O CH3
CH3
97
Reactions
aldehydes and ketones are generally synthesized
by the oxidation of alcohols therefore, reduction of an aldehyde or ketone results in an alcohol
98
Carbonyl Group
C=O group is highly polar many reactions involve addition across C=O, with positive part attached to O
Addition to C=O
100
Carboxylic Acids

RCOOH sour tasting weak acids citric acid
O O CH2 C OH HO C C OH CH2 C OH O
found in citrus fruit
ethanoic acid = acetic acid

vinegar insect bites and stings
CH3 C OH
methanoic acid = formic acid
O H C OH
101
Carboxylic Acids
made by the oxidation of
aldehydes and alcohols
OH on the end of the chain
O C H oxidation O C OH
always on main chain

has highest precedence
benzaldehyde
benzoic acid
C of group always C1
OH H3C CH2
oxidation
O H3C C OH ethanoic acid
position not indicated in name ethanol
change ending to oic acid

Naming Carboxylic Acids
103
Esters
RCOOR sweet odor made by reacting carboxylic acid
with an alcohol methyl butanoate RaCOOH + RbOH RaCOORb + H2O O name alkyl group from alcohol, then C OH acid name with oate ending
precedence over carbonyls, but not carboxylic acid number from end with ester group
O C CH3 O
aspirin
104
Naming Esters
105
a condensation reaction is any organic reaction

driven by the removal of a small molecule, like water acid esters anhydrides are made by arethe made condensation by the condensation reaction reaction betweenbetween a carboxylic 2 carboxylic acid andacid an alcohol molecules
O R C OH
Condensation Reactions
the reaction is driven acid catalyzed by heat

O O R' R C O O C
+
HO
+ R'
HOH
106
Synthesis of Aspirin (Acetylsalicylic Acid)
107
Ethers
R O R ether = diethyl ether = CH3CH2OCH2CH3
anesthetic
to name ethers, name each alkyl group

attached to the O, then add the word ether to the end
diethyl ether
Amines

N containing organic molecules very bad smelling form when proteins decompose organic bases name alkyl groups attached to the N, then add the word amine to the end
NH2 H3C CH2
ethylamine
H3C NH H3C CH2

ethylmethylamine
H2NCH2CH2CH2CH2NH2 putrescine H2NCH2CH2CH2CH2CH2NH2 cadaverine

109
many amines are biologically active

dopamine a neurotransmitter epinephrine an adrenal hormone pyridoxine vitamin B6
HO HO CH2CH2NH2 dopamine
Amines
alkaloids are plant products that are

alkaline and biologically active
toxic coniine from hemlock cocaine from coca leaves nicotine from tobacco leaves mescaline from peyote cactus morphine from opium poppies
N N CH3 nicotine
110
Amine Reactions
weak bases
react with strong acids to form ammonium salts
RNH2 + HCl RNH3+Cl react with carboxylic acids in a condensation reaction to form amides RCOOH + HNHR RCONHR + H2O
Macromolecules
polymers are very large molecules made by
repeated linking together of small molecules
monomers
natural modified natural polymers synthetic composites

plastics, elastomers (rubber), fabrics, adhesives additives such as graphite, glass, metallic flakes
112
Natural Polymers
polysaccharides
cellulose (cotton) starch
proteins nucleic acids (DNA) natural latex rubber, etc. shellac amber, lignin, pine rosin asphalt, tar
113
Modified Natural Polymers

Cellulose Acetate Vulcanized Rubber Gun Cotton Celluloid Gutta Percha
ping-pong balls
Rayon film
Casein
fill space for root canal buttons, mouldings, adhesives

114
Polymerization
the process of linking the monomer units together two processes are addition polymerization and
condensation polymerization monomers may link head-to-tail, or head-to-head, or tail-to-tail

head-to-tail most common regular pattern gives stronger attractions between chains than random arrangements
115
H H C Cl
H C H
H C Cl
H C H
Head-to-Tail
Head Tail Head Tail
H C
H C
C
H
Tail
Cl Cl
Head-to-Head, Tail-to-Tail
116
Head Head Tail
Addition Polymerization
monomers add to the growing chain in
such a manner that all the atoms in the original monomer wind up in the chain
no other side products formed, no atoms eliminated
first monomer must open to start

reaction
done with heat or addition of an initiator
chain reaction
each added unit ready to add another
Addition Polymerization
initiator
H
initiator
etc.
H C H H
H
H C C
H
H
C Cl
H C H C H C Cl H C H H C Cl H C H H C H
Cl H H C Cl H H C Cl
H C H H C H H C Cl +
H
C C
H
C Cl
Cl H
H
Cl
H H H
H
H
C H
C + H Cl
C Cl
Condensation Polymerization
monomer units are joined by removing small
molecules from the combining units
polyesters, polyamides lose water
no initiator needed chain reaction each monomer has two reactive ends, so chain
can grow in two directions
Condensation Polymerization
+
O O
HO
OH + HO
CH2
CH2
OH
O HO C
O C O CH2 CH2 OH
+ H2O
120
polyamides good physical properties

affected by moisture
Nylon
very good heat resistance excellent chemical resistance excellent wear resistance nylon 6,6 made by condensing 1,6hexandiamine, H2N(CH2)6NH2, with hexandioic acid, HOOC(CH2)4COOH O O
HN (CH2)6 NH C (CH2)4 C
121
122

Organic Chemistry Chapter on Structure and Properties of Carbon Compounds

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Organic Chemistry Chapter on Structure and Properties of Carbon Compounds

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Chemistry: A Molecular Approach, 1st Ed.

Chapter 20 Organic Chemistry

Structure Determines Properties

Carbon has versatile bonding patterns

Carbon compounds generally covalent

C - C bonds unreactive (very stable)

Bond Energies and Reactivities

SPONTANEOUS 3 BURNS IN AIR EXTREMELY REACTIVE REACTIVE

Tro, Chemistry: A Molecular Approach

Allotropes of Carbon - Diamond

Tro, Chemistry: A Molecular Approach

Allotropes of Carbon - Graphite

Tro, Chemistry: A Molecular Approach

Tro, Chemistry: A Molecular Approach

may be chains or rings chains may be straight or branched

saturated aliphatic hydrocarbons are called

Tro, Chemistry: A Molecular Approach

unsaturated aliphatic hydrocarbons that contain CC

Tro, Chemistry: A Molecular Approach

H2 C C H C 2 CH 3 H3C C C CH 3 H H CH3 C C 2C CH CH3 2 C H3C H3C C H H C 2 CH 3 C H2

alkanes alkenes alkynes

Tro, Chemistry: A Molecular Approach

Condensed Structural Formulas

follow normal bonding patterns

() used to indicate more than 1 identical

multiple bonds indicated

Tro, Chemistry: A Molecular Approach

Tro, Chemistry: A Molecular Approach

Isomers = different molecules with the same

molecular formula Structural Isomers = different pattern of atom attachment

Stereoisomers = same atom attachments, different

Tro, Chemistry: A Molecular Approach

C C C H H C C C Structural Isomers of C4H10

Tro, Chemistry: A Molecular Approach

Rotation about a bond is not isomerism

Tro, Chemistry: A Molecular Approach

Possible Structural Isomers

Nonsuperimposable Mirror Images

Tro, Chemistry: A Molecular Approach

Optical Isomers of 3-methylhexane

Tro, Chemistry: A Molecular Approach

Plane Polarized Light

Tro, Chemistry: A Molecular Approach

a pair of enantiomers have all the same physical

an equimolar mixture of the pair is called a racemic

Tro, Chemistry: A Molecular Approach

Chemical Behavior of Enantiomers

Tro, Chemistry: A Molecular Approach

saturated branched or unbranched

Name Methane Ethane Propane Butane Pentane Hexane

Formula CH4 CH3CH3 CH3CH2CH3 CH3CH2CH2CH3 CH3CH2CH2CH2CH3 CH3CH2CH2CH2CH2CH3

Boiling Point -162C -89C -42C 0C 36C 69C

Tro, Chemistry: A Molecular Approach

certain functional groups

More Alkyl Groups

(CH3)3C-, tert- B U TYL

Examples of Naming Alkanes

Example Name the alkane

1) find the longest continuous C chain and use it

CH3CHCH2CHCH3 CH3 CH3

since the longest chain has 5 C the base name is pentane

Example Name the alkane