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Chapter 2 Representative Carbon Compounds

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Chapter 2 Representative Carbon Compounds 2.1 Carbon-Carbon Covalent Bonds 1) Carbon s ability to form as many as four strong bonds to other carbon atoms and to ... – PowerPoint PPT presentation

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Title: Chapter 2 Representative Carbon Compounds


1
Chapter 2 Representative Carbon Compounds
2.1 Carbon-Carbon Covalent Bonds
1) Carbons ability to form as many as four
strong bonds to other carbon atoms and to form
strong bonds to hydrogen, oxygen, sulfur,
nitrogen and phosphorous.
2) Carbon can make the vast number of different
molecules Required for complex living organisms.
2
2.2 Methane and Ethane Representative alkanes
1)Methane and ethane are two members of a broad
family of Organic compounds called hydrocarbon
(?)
2) Hydrocarbons are compounds whose molecules
contain only Carbon and hydrogen atoms--------
alkanes
3) Hydrocarbons whose molecules have a
carbon-carbon double bond are called alkenes,
and those with a carbon-carbon triple bond are
called alkynes
3
Saturated compounds and unsaturated compounds
(????????????)
  • Generally speaking, compounds such as the
    alkanes,
  • whose Molecules contain only single bonds are
    referred
  • to as saturated compounds

2) Compounds with multiple bonds, such as
alkenes, alkynes, and aromatic hydrocarbons are
called unsaturated compounds
4
2.2A Sources of Methane
  • The atmosphere of earth
  • a major component of the natural gas
  • Living organisms
  • Coal, ocean trenches, in mud, in sewage, and in
  • cows stomachs.

5
2.2B The Structure of ethane
1) C----SP3-hybridized carbon atoms
2) Ethane contain 6 C-H and 1 C-C sigma bond
6
2.3 Alkenes Compounds containing the
carbon-carbon double bond------Ethene and Propene
Hydrocarbons whose molecules contain a
carbon-carbon double bond are called alkenes.
Ethene (ethylene) and Propene (propylene)
7
2.4 Orbital Hybridization and Structure of
Alkenes
  • C----SP2-Hybridized carbon atoms
  • One 2p orbital is left unhybridized
  • 3) How to form pi-bond ?

8
2.4A Restricted rotation and the double bond
9
2.4B Cis-Trans isomerism ? ? ? ?
10
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12
2.5 Alkynes Compounds containing the
carbon-carbon triple bond Ethyne (Acetylene)
and propyne
Alkynes----Hydrocarbons in which two carbon atoms
Share three pairs of electrons between them, and
are thus bonded by a triple bond, are called
alkynes (??)
13
2.6 Orbital Hybridization and the structure of
alkynes
1) C----sp hybridization
2) Two sp orbitals
3) The remaining two 2p orbital are not
hybridized to form pi-bonds
14
2.6A Bond Lengths of ethyne, ethene, and ethane
The carbon-carbon triple bond is shorter than the
carbon double bond, and the carbon-carbon double
bond is shorter than the carbon-carbon single
bond.
1) Ethyne-----C sp (50 s and 50 p)
2) Ethene----C sp2 (25 s and 75 p)
3) Ethane----C sp3 (20 s and 80 p)
15
2.7 Benzene A representative aromatic
hydrocarbon ??
16
2.8 Functional Groups (???)
The molecules of compounds in a particular family
are characterized by the presence of a certain
arrangement of atoms Called a functional groups
1) Ethyne-----triple bond
2) Ethene-----double bond
3) Ethane--- C-H and C-C bond
4) Alcohol----Hydroxyl group (-OH ??) (R-OH)
17
2.8 Alkyl groups and the symbol R (??)
They are groups that would be obtained by
removing a hydrogen Atom from an alkane (??)
18
2.9 Alkyl halides or haloalkanes (RX, XF, Cl,
Br, I) ????
Although we use the symbols 10, 20, 30, we do not
say first degree, second degree, and third
degree we say primary, secondary, and tertiary.
19
2.10 Alcohols ?
  1. As hydroxyl derivatives of alkanes.
  2. As alkyl derivatives of water.

20
Primary alcohol, secondary alcohol and tertiary
alcohol
21
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23
2.11 Ethers ?
Ethers have the general formula R-O-R or R-O-R
may be an alkyl group different from R. They can
be thought of as derivatives of water in which
both hydrogen atoms have been Replaced by alkyl
groups. The bond angle at the oxygen atom Of an
ether is only slightly larger than that of water.
24
2.12 Amines ?
This classification is based on the number of
organic groups That are attached to the nitrogen
atom
25
The Structures of Amines
  • It is a trigonal pyramidal shape, like ammonia.
  • 2. The bond angle is 108.7O

3. The nitrogen atom of an amine is a SP3
hybridized, this means that the unshared
electron pair occupies an sp3 orbital.
26
2.13 Aldehydes and ketones ? ? ?
Aldehydes and ketones both contain the carbonyl
group---a group in which a carbon atom has a
double bond to oxygen

??
Aldehydes
Ketones
Formaldehyde HCHO Acetone
CH3COCH3
Acetaldehyde CH3CHO Ethyl methyl ketone
CH3CH2COCH3
Benzaldehyde C6H5CHO Acetophone
C6H5COCH3
27
Organic Chemistry ???? (????)
  • ?????? ??
  • ?????????

28
Chapter 2 Representative Carbon Compounds
2.1 Carbon-carbon covalent bonds
  • 2.2 The structure of methane (?????)

2.3 Alkenes (??)
29
2.3 Alkenes Compounds containing the
carbon-carbon double bond------Ethene and Propene
Hydrocarbons whose molecules contain a
carbon-carbon double bond are called alkenes.
Ethene (ethylene) and Propene (propylene)
30
2.4 Orbital Hybridization and Structure of
Alkenes
  • C----SP2-Hybridized carbon atoms

31
2) How two p orbitals combine to form pi-bond
32
3) How two p orbitals combine to form two pi
molecular orbitals
33
4) How about pi-electrons?
34
2.4A Restricted rotation and the double bond
35
2.4B Cis-Trans isomerism ? ? ? ?
36
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38
Cis-trans isomers have different physical
properties
39
Problem 2.1 Which of the following alkenes can
exist as cis-trans isomers? Write their
structures.
40
2.5 Alkynes Compounds containing the
carbon-carbon triple bond Ethyne (Acetylene)
and propyne
Alkynes----Hydrocarbons in which two carbon atoms
Share three pairs of electrons between them, and
are thus bonded by a triple bond, are called
alkynes (??)
41
2.6 Orbital Hybridization and the structure of
alkynes
1) C----sp hybridization
2) Two sp orbitals
3) The remaining two 2p orbital are not
hybridized to form pi-bonds
42
2.6A Bond Lengths of ethyne, ethene, and ethane
The carbon-carbon triple bond is shorter than the
carbon double bond, and the carbon-carbon double
bond is shorter than the carbon-carbon single
bond.
1) Ethyne-----C sp (50 s and 50 p)
2) Ethene----C sp2 (25 s and 75 p)
3) Ethane----C sp3 (20 s and 80 p)
43
2.7 Benzene A representative aromatic
hydrocarbon ??
44
2.8 Functional Groups (???)
The molecules of compounds in a particular family
are characterized by the presence of a certain
arrangement of atoms Called a functional groups
1) Ethyne-----triple bond
2) Ethene-----double bond
3) Ethane--- C-H and C-C bond
4) Alcohol----Hydroxyl group (-OH ??) (R-OH)
45
2.8 Alkyl groups and the symbol R (??)
They are groups that would be obtained by
removing a hydrogen Atom from an alkane (??)
46
2.9 Alkyl halides or haloalkanes (RX, XF, Cl,
Br, I) ????
Although we use the symbols 10, 20, 30, we do not
say first degree, second degree, and third
degree we say primary, secondary, and tertiary.
47
2.10 Alcohols ?
  1. As hydroxyl derivatives of alkanes.
  2. As alkyl derivatives of water.

48
Primary alcohol, secondary alcohol and tertiary
alcohol
49
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51
2.11 Ethers ?
Ethers have the general formula R-O-R or R-O-R
may be an alkyl group different from R. They can
be thought of as derivatives of water in which
both hydrogen atoms have been Replaced by alkyl
groups. The bond angle at the oxygen atom Of an
ether is only slightly larger than that of water.
52
2.12 Amines ?
This classification is based on the number of
organic groups That are attached to the nitrogen
atom
53
The Structures of Amines
  • It is a trigonal pyramidal shape, like ammonia.
  • 2. The bond angle is 108.7O

3. The nitrogen atom of an amine is a SP3
hybridized, this means that the unshared
electron pair occupies an sp3 orbital.
54
2.13 Aldehydes and ketones ? ? ?
Aldehydes and ketones both contain the carbonyl
group---a group in which a carbon atom has a
double bond to oxygen

??
Aldehydes
Ketones
Formaldehyde HCHO Acetone
CH3COCH3
Acetaldehyde CH3CHO Ethyl methyl ketone
CH3CH2COCH3
Benzaldehyde C6H5CHO Acetophone
C6H5COCH3
55
2.14 Carboxylic acids, amides, and esters
(??,????)
  • 2.14A Carboxylic acids
  • COOH is called the carboxyl group
    (carbonylhydroxyl)

56
Examples of carboxylic acids are formic acid(??),
acetic acid(??), and benzoic acid(???)
57
2.14B Amides
  • Amides have the formulas RCONH2, RCONHR, or
    RCONRR

58
2.14C Esters
  • Esters have the general formula RCO2R (or RCOOR)

59
How to make esters?
Esters can be made from an acid and an alcohol
through the loss of a molecule of water.
60
2.15 Summary of important families of organic
compounds
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62
2.16 Physical properties and molecular structure
  • Melting points and boiling points
  • Ion-Ion forces
  • Dipole-dipole forces
  • Hydrogen bonds
  • Van der Walls forces
  • Solubilities (???)

63
2.16 Ion-ion forces
64
2.16B Dipole-dipole forces
  • Most organic molecules are not fully ionic, but
    rather have a permanent dipole moment

65
2.16C Hydrogen bonds
  • Hydrogen bonds----Very strong dipole-dipole
    attractions occur between hydrogen atoms bonded
    to small, strongly electronegative atoms. This
    type of intermolecular force is called a hydrogen
    bond.
  • The hydrogen bond is weaker than an ordinary
    covalent bond, but is much stronger than the
    dipole-dipole interactions that occur in acetone

66
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Tert-Butyl alcohol has a much higher melting
point than the other isomeric alcohols shown here
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