organic chemistry topic 10.1.1 – 10.1.8 choncchonc 4 1 2 3 4 bonds
TRANSCRIPT
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Organic Chemistry
Topic 10.1.1 – 10.1.8
HONCC
1 2 3 44 bonds
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What is organic chemistry?• study of carbon, the compounds it makes,
and the reactions it undergoes• over 16 million carbon-containing
compounds are known• because the C-C single bond (348 kJ mol-1)
and the C-H bond (412 kJ mol-1) are strong, carbon compounds are stable
• carbon can form chains and rings
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Homologous series/compounds (10.1.1)
• related compounds that have the same functional group (groups of atoms found within molecules that are involved in the chemical reactions characteristic of those molecules)
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• differ from each other by a CH2 unit• can be represented by a general
formula– examples:
• CnH2n+2 (alkanes) or CnH2n (alkenes) or…
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• have similar chemical properties• have physical properties that vary
in a regular manner as the number of carbon atoms increases– Example: the alkanes
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Trends in boiling points of members of a homologous series (10.1.2)
• melting point and boiling point increase with more carbon atoms
• Why?– intermolecular
forces increase– adding a CH2 adds
more electrons• this increases the
Van der Waal’s forces
AlkaneAlkane FormulFormulaa
Boiling Boiling Pt./Pt./ooCC
methanmethanee
CHCH44 -162.0-162.0
ethaneethane CC22HH66 -88.6-88.6
propanpropanee
CC33HH88 -42.2-42.2
butanebutane CC44HH1010 -0.5-0.5
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Empirical, molecular & structural formulas (10.1.3)
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• empirical formula– simplest ratio
of atoms in a molecule
• molecular formula– actual
numbers of atoms in a molecule
Empirical Empirical FormulaFormula
MoleculaMolecular r
FormulaFormula
CHCH44 CHCH44
CHCH33 CC22HH66
CHCH22OO CC66HH1212OO66
CHCH22 CC44HH88
CHCH22 CC88HH1616
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structural formula• unambiguously shows how the atoms are
bonded together
• can use condensed structural formulas – bonds are omitted, repeated groups
put together, side chains put in brackets• CH3CH2CH2CH2CH2CH3
–or even CH3(CH2)4CH3 • CH3CH(CH3)CH3
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condensed
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skeletal formula– not accepted in the IB for answers but
often used in questions– every “corner” represents a carbon– hydrogens are implied
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Isomers (10.1.4)
• (structural) isomers: compounds with the same molecular formula but different structure (arrangement of atoms)
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• different isomers are completely different ifferent isomers are completely different compoundscompounds
• have different physical properties such as have different physical properties such as melting point and boiling pointmelting point and boiling point
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Structural Formulas
for C4H10O Isomers
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• hydrocarbon chains where all the bonds between hydrocarbon chains where all the bonds between carbons are SINGLE bondscarbons are SINGLE bonds
• CnH2n+2
• draw out and write the structural formulas for all isomers that can be formed by: – CH4
– C2H6 – C3H8
– C4H10
– C5H12
– C6H14
Richard Thornley 10.1.5 2:54
Structural formulas for the isomers of non-cyclic alkanes up to C6 (10.1.5)
Alkanes
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1. Richard Thornley 3:352. Determine the longest carbon chain
– Use the prefix to denote the number carbons
Naming the isomers (IUPAC) of non-cyclic alkanes up to C6 (10.1.6)
11 MMeth-eth-
22 EEth-th-
33 PProp-rop-
44 BBut-ut-
55 Pent-Pent-
66 Hex-Hex-
Monkeys
Eat
Peeled
Bananas
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3. use the suffix “-ane” to indicate that the substance is an alkane
4. number the carbons in the chain consecutively, starting at the end closest to a substituent (groups attached to the main chain/most busy end)
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5. name and number the location of each substituent– the name of the substituent will be written before the
main chain and will end with “–yl” (or just memorize the below)
• CH3 is methyl
• C2H5 is ethyl
• C3H7 is propyl
And with 2 or more side chains: 5. use prefixes di-, tri-, tetra-, to indicate when
there are multiple side chains of the same type6. use commas to separate numbers and
hyphens to separate numbers or letters.7. name the side chains in alphabetical order
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• How about C5H12? The isomers are:
Pentane 2-methyl-butane 2,2-dimethyl propane
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Nomenclature PracticeNomenclature Practice
CH3 CH3
CH3
CH3
Cl
Name this compound
Step #1: For a branched hydrocarbon, the longest continuous chain of carbon atoms gives the root name for the hydrocarbon
152 43
9
6
87
9 carbons = nonane
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Nomenclature PracticeNomenclature PracticeName this compound
CH3 CH3
CH3
CH3
Cl
152 43
9
6
87
9 carbons = nonane
Step #2: When alkane groups appear as substituents, they are named by dropping the -ane and adding -yl.
CH3 = methyl
chlorine = chloro
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Nomenclature PracticeNomenclature PracticeName this compound
CH3 CH3
CH3
CH3
Cl
152 43
9
6
87
9 carbons = nonane
CH3 = methyl
chlorine = chloro
Step #3: The positions of substituent groups are specified by numbering the longest chain of carbon atoms sequentially, starting at the end closest to the branching.
1 9 NOT 9 1
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Nomenclature PracticeNomenclature PracticeName this compound
CH3 CH3
CH3
CH3
Cl
152 43
9
6
87
9 carbons = nonane
CH3 = methyl
chlorine = chloro
Step #4: The location and name of each substituent are followed by the root alkane name. The substituents are listed in alphabetical order (irrespective of any prefix), and the prefixes di-, tri-, etc. are used to indicate multiple identical substituents.
2-chloro-3,6-dimethylnonane
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Structural formulas for the isomers of the straight chain alkenes up to C6 (10.1.7)
• alkenes have a double bond between two or more of the carbons
• CnH2n
• draw out and write the structural formulas for all isomers that can be formed by each
– C2H4
– C3H6
– C4H8
– C5H10
– C6H12
Alkenes
Richard Thornley 10.1.7 (1:37)
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1. suffix changes to “-ene”2. when there are 4 or more carbon atoms
in a chain, the location of the double bond is indicated by a number
3. begin counting the carbons closest to the end with the C=C bond
– numbering the location of the double bond(s) takes precedence over the location of any substituents
1-butene 2-butenebut-1-ene but-2-ene
Naming the isomers (IUPAC) of straight chain alkenes up to C6 (10.1.8)
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ene
Naming Practice!!!
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
choose the correct ending
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ene
determine the longest carbon chain with the double bond
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
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assign numbers to each carbon
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
ene
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assign numbers to each carbon
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
ene
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1-hexene ene
attach prefix (according to # of carbons)
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
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CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
determine name for side chains
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
1-hexene 1-hexene
ethyl
methyl
methyl
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CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
2-ethyl-4-methyl-4-methyl-1-hexene
ethyl
methyl
methylattach name of branches alphabetically
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group similar branches
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
2-ethyl-4-methyl-4-methyl-1-hexene
ethyl
methyl
methyl
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group similar branches
CH3 CH2 C
CH2
CH2 C
CH2
CH3
CH3
CH3
CH3 CH2 C2
CH21
CH23
C4
CH25
CH3
CH3
CH36
2-ethyl-4,4-dimethyl-1-hexene
or 2-ethyl-4,4-dimethyl hex-1-ene
ethyl
methyl
methyl
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2-butene
propene
CH3 CH CH2
CH3 CH CH CH3
CH3 CH CH C
CH3 CH3
CH3
2,4-dimethyl-2-pentene2,4-dimethyl pent-2-tene
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b) same
c) 4,5 dimethyl-2-hexene
a) 3,3-dimethyl-1-pentene
CH2 CH C CH2 CH3
CH3
CH3
CH3 C CH CH2
CH3
CH2 CH3
CH CH CH3
CH3
CC
CH3
CH3