Beruflich Dokumente
Kultur Dokumente
Nivaldo Tro
H2N-NH2
HO-OH
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
aromatic hydrocarbons
Tro, Chemistry: A Molecular Approach 7
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
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 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
Tro, Chemistry: A Molecular Approach
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
CH HC CH 22 H2C H H2 C CH2 2 CH C C 2 C H2 H2
H C C2 H
H2 C
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
Line-Angle Formulas
each angle, and beginning and end represent a C
atom H omitted on C
included on functional groups
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
Tro, Chemistry: A Molecular Approach
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
Isomerism
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
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
22
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
Tro, Chemistry: A Molecular Approach 24
C C C C C C C C C C C C C C C
C C C C C C C C
Ex 20.1 Write the structural formula and carbon skeleton formula for C6H14
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
Ex 20.1 Write the structural formula and carbon skeleton formula for C6H14
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
Tro, Chemistry: A Molecular Approach 27
mirror image cannot be rotated so all its atoms align with the same atoms of the original molecule
Tro, Chemistry: A Molecular Approach 28
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
30
31
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
32
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
Lewis Structure
H C H H H
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
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
Tro, Chemistry: A Molecular Approach
CH3CH2-, ETHYL
CH3CH2CH2-, PROPYL
(CH3)2CH-, ISOPROPYL
38
CH3CH2(CH3)CH-, sec-BUTYL
(CH3)2CHCH2-, ISOBUTYL
CH3 H 3C C CH3
Tro, Chemistry: A Molecular Approach
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
Tro, Chemistry: A Molecular Approach 40
then assign numbers to each substituent based on the number of the main chain C its attached to
CH3CHCH2CHCH3 CH3
2
CH3
4
43
CH3CHCH2CHCH3 CH3
2
CH3
4
44
45
3-ethyl-2-methylpentane
46
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
48
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
51
Alkenes
ethene = ethylene
H C C H H
H
propene
H C C CH3 H
52
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
55
Alkynes
ethyne = acetylene
H C C H
propyne
H C C CH3
56
58
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
Tro, Chemistry: A Molecular Approach 59
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
60
since the longest chain with the double bond has 6 C the base name is hexene
Tro, Chemistry: A Molecular Approach 61
there are 2 substituents one is a 1 C chain, called methyl the other one is a 2 C chain, called ethyl
Tro, Chemistry: A Molecular Approach 62
H2 C CH3
4
H3 C CH
5 6
C CH CH3
3 2 1
H2 C CH3
63
H3 C CH
4 5 6
H2 C CH3
3 2 1
3ethyl 4methyl2hexene
C CH CH3
H2 C CH3
Tro, Chemistry: A Molecular Approach 64
65
CH C CH 3 2 4
5 6
CH3
1
3,4-dimethyl-3-hexene
66
CH3
since the longest chain with the triple bond has 7 C the base name is heptyne
Tro, Chemistry: A Molecular Approach 67
CH3
CH3
CH3 CH CH2 CH C 7 6 5 4 3
6 CH3
C
2
CH3
1
HC
CH3
CH3
69
CH3 CH CH2 CH C 7 6 5 4 3
6 CH3
C
2
CH3
1
HC
CH3
4isopropyl 6methyl2heptyne
70
CH3
Tro, Chemistry: A Molecular Approach
71
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
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
heat or UV light
H Cl H C C H + H Cl H H
77
Hydrogenation = adding H2
converts unsaturated molecule to saturated alkene or alkyne + H2 alkane
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
CH2CH2CH3
fluorobenzene
propylbenzene
toluene
Tro, Chemistry: A Molecular Approach
aniline
phenol
styrene
82
H2C CH CH2
CH CH2
CH3
4-phenyl-1-hexene
Tro, Chemistry: A Molecular Approach 83
3 2
CH3
1 2
CH3
1 Br 1-bromo-3-fluorobenzene
Tro, Chemistry: A Molecular Approach
1,2-dimethylbenzene
84
CH3
CH3
Cl
Cl
Br
Br
Cl
86
Br
Br
Cl
1-chloro-4-fluorobenzene
88
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
Tro, Chemistry: A Molecular Approach
CH3OH
functional group
90
91
Alcohols
methanol = CH3OH
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
4-ethyl-4-methyl-3-hex-5-enol
Tro, Chemistry: A Molecular Approach 93
Reactions of Alcohols
Nucleophilic Substitution
CH3
CH3 CH3
Oxidation
CH2OH CH3
CH3 OH
-2H
CHO CH3
-2H
COOH
+ Na CH3ONa+ + H2
94
O C
formaldehyde
acetone = CH3C(=O)CH3
Tro, Chemistry: A Molecular Approach
acetone
95
CH2CH2CH3
vanillin = vanilla
HO
benzaldehyde = almonds
O C H
cinnamaldehyde = cinnamon
H C C H O C H
96
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
Tro, Chemistry: A Molecular Approach 99
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
CH3 C OH
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
benzaldehyde
benzoic acid
C of group always C1
OH H3C CH2
oxidation
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
Tro, Chemistry: A Molecular Approach
O C CH3 O
aspirin
104
Naming Esters
105
O R C OH
Condensation Reactions
+
HO
+ R'
HOH
106
107
Ethers
R O R ether = diethyl ether = CH3CH2OCH2CH3
anesthetic
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
Amines
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
Tro, Chemistry: A Molecular Approach 111
Macromolecules
polymers are very large molecules made by
repeated linking together of small molecules
monomers
112
Natural Polymers
polysaccharides
cellulose (cotton) starch
proteins nucleic acids (DNA) natural latex rubber, etc. shellac amber, lignin, pine rosin asphalt, tar
113
Rayon film
Casein
Polymerization
the process of linking the monomer units together two processes are addition polymerization and
115
H H C Cl
H C H
H C Cl
H C H
Head-to-Tail
H C
H C
C
H
Tail
Cl Cl
Head-to-Head, Tail-to-Tail
116
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
chain reaction
each added unit ready to add another
Tro, Chemistry: A Molecular Approach 117
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
Tro, Chemistry: A Molecular Approach 119
Condensation Polymerization
+
O O
HO
OH + HO
CH2
CH2
OH
O HO C
O C O CH2 CH2 OH
+ H2O
120
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
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