chapter 12_13_14_16_17 Organic Nomenclature

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Transcript chapter 12_13_14_16_17 Organic Nomenclature

Fundamentals of General,
Organic and Biological
Chemistry
6th Edition
Chapter Twelve
Introduction to Organic
Chemistry: Alkanes
James E. Mayhugh
Copyright © 2010 Pearson Education, Inc.
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12.1 The Nature of Organic
Molecules
► Organic chemistry: The study of carbon compounds.
► Carbon ALWAYS forms four bonds.
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► Carbon’s 4 bonds can be any combination of single,
double and triple bonds
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12.4 Drawing Organic Structures
Condensed structure: A shorthand way of drawing
structures in which C-C and C-H bonds are
understood rather than shown.
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12.4 Drawing Organic Structures
Line structure: An even shorter notation:
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12.2 Families of Organic Molecules:
Functional Groups
► Organic compounds are put into families
(categories) according to
►The types of atoms attached to the carbons
►The types of bonds between the carbons
►Single, double, triple
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Organic Nomenclature
► Basic naming system (nomenclature):
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Hydrocarbon Nomenclature
► The simplest group of Families are the
hydrocarbons… compounds containing only
carbon and hydrogen
►All carbon-carbon single bonds: alkanes
►At least one C=C double bond: alkenes
►At least one C  C triple bond: alkynes
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Hydrocarbon Nomenclature
► Hydrocarbons can be
►“straight” chain
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Hydrocarbon Nomenclature
► Hydrocarbons can be
►“straight” chain
► branched chain
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Hydrocarbon Nomenclature
► Hydrocarbons can be
►“straight” chain
► branched chain
► cyclic
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12.6 Naming Alkanes
► Suffix: -ane
► Parent : based on # of Carbons in longest,
continuous chain
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1 carbon
2 carbons
3 carbons
4 carbons
5 carbons
6 carbons
7 carbons
8 carbons
9 carbons
10 carbons
methethpropbutpenthexheptoctnondec14
12.6 Naming Alkanes
►Examples of “Straight chain” alkanes:
CH3CH2CH3
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► Branched-chain
alkanes
(Rules are on following slides)
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► What is the chemical
formula of this
molecule?
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► Branched-chain
alkanes
(Rules are on following slides)
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12.6 Naming Branched-Chain
Alkanes
► Branched-chain alkanes have “substituents”
branching off of the main chain.
► For hydrocarbons, these substituents (or “branches”)
are also hydrocarbons
►# of carbons in branch: normal prefix
►Suffix of hydrocarbon branch: -yl
►Name must include WHICH carbon of the main
chain the branch is connected to.
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12.6 Naming Branched Alkanes
► STEP 1: Name the main chain (parent + suffix).
Find the longest continuous chain of carbons!
► STEP 2: Number the carbon atoms in the main
chain. Begin at the end nearer the first branch point
► STEP 3: Identify the branching substituents, and
number each according to its point of attachment to
the main chain
► STEP 4:Write the name as a single word,
►If two or more identical substituents are present,
use one of the prefixes di-, tri-, tetra►If two or more different substituent groups are
present, cite them in alphabetical order
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12.9 Naming Cyclic Alkanes
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12.9 Naming Cyclic Alkanes
► Naming rules are mostly the same as for other
alkanes
► Additional Rules:
►The ring is ALWAYS the main chain
►The prefix “cyclo” is added to the name of the
main chain
►If only 1 branch, it doesn’t need to be numbered
►If more than one branch, number the carbons in
the ring to get the lowest combination of numbers
of branch locations.
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End of Chapter 12
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Fundamentals of General,
Organic and Biological
Chemistry
6th Edition
Chapter Thirteen
Alkenes andAlkynes
James E. Mayhugh
Copyright © 2010 Pearson Education, Inc.
Chapter Seven
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13.2 Naming Alkenes and Alkynes
(rules on following slides)
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13.2 Naming Alkenes and Alkynes
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13.2 Naming Alkenes and Alkynes
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13.2 Naming Alkenes and Alkynes
► Very similar rules as for alkanes
► Additional rules:
►Choose longest chain that contains the
double or triple bond
►Suffix for alkenes: -ene
►Suffix for alkynes: -yne
►Include a number with the parent to
indicate which carbon the double/triple
bond starts on.
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►3-methylcylclopentene
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► Cyclic alkene special rules
►Carbons 1 and 2 MUST go “through” the double
bond
►If there is more than one double bond, number
the ring to give the double bonds the lowest
numbers… then worry about branches.
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►5-ethyl-1,3-cylclohexene
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Isomers
► 2 or more molecules with the same number of
each atom, but are connected differently.
► These molecules will have different names.
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Isomers
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End of Chapter 13
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Fundamentals of General,
Organic and Biological
Chemistry
6th Edition
Chapter Fourteen
Some Compounds With
Oxygen or a Halogen
James E. Mayhugh
Copyright © 2010 Pearson Education, Inc.
Chapter Seven
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14.1 Alcohols and Ethers
► An alcohol has an –OH covalently bonded to a carbon
chain.
► These compounds are NOT basic.
► An ether has an O in the midst of a carbon chain.
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14.3 Naming Alcohols (rules on following slides)
4-methyl-1-cyclohexanol
1-propanol
methanol
(only 3 carbons, not 4)
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14.3 Naming Alcohols
► 1. Number the longest carbon chain starting at the
end that gets you to the OH the quickest.
► 2. Suffix: replace the “e” at the end of the normal
name for the main chain with “ol”
► 3. Denote location of the OH the same way you
show the location of a double or triple bond
► 4. Name and slow location of any hydrocarbon
branches.
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14.8 Ethers
Ethers are named by identifying the two carbon
“branches” attached to the oxygen atom (in alph.
order) and adding the word ether.
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14.8 Ethers
Butyl propyl ether
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14.10 Halogen Containing
Compounds
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14.10 Halogen Containing
Compounds
► Halogens: Fluorine, chlorine, bromine, iodine
►As a branch: fluoro, chloro, bromo, iodo
► Halogen branches are given “numbering
preference” over hydrocarbon branches
►But NOT over any substituent that determines the
family of the compound (like alcohols, double
bonds, etc.)
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End of Chapter 14
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Fundamentals of General,
Organic and Biological
Chemistry
6th Edition
Chapter Sixteen
Aldehydes and Ketones
James E. Mayhugh
Copyright © 2010 Pearson Education, Inc.
Chapter Seven
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16.1 The C=O group
► Both aldehydes and ketones contain a C=O
group
► They are NOT alkenes… alkenes have C=C
bonds
► The difference between aldehydes and
ketones is the placement of the C=O group.
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16.2 Aldehydes
CH3CHO
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16.2 Aldehydes
Propanal
3-methylbutanal
CH3CHO
Ethanal
methanal
(common name: formaldehyde)
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16.1 Aldehydes
►Aldehydes:
►The Carbon of the C=O group is one of the
end carbons
►Suffix: -al
►No need to show its number… it’s ALWAYS
“1” if it’s an aldehyde.
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16.2 Ketones
CH3COCH2CH2CH3
(how can you know it’s not an ether??)
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16.2 Ketones
2-butanone
4-methyl-3-hexanone
CH3COCH2CH2CH3
(how can you know it’s not an ether??)
2-pentanone
cyclohexanone
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16.1 Ketones
►Ketones:
►The Carbon in the C=O group is one of the
INTERIOR carbons
►Suffix: -one
►Location of the =O must be numbered (except
for propanone and butanone)
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End of Chapter 16
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Fundamentals of General,
Organic and Biological
Chemistry
6th Edition
Chapter Seventeen
Carboxylic Acids
James E. Mayhugh
Copyright © 2010 Pearson Education, Inc.
Chapter Seven
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17.1 Carboxylic Acids
► Carboxylic acids look like a combination of
an alcohol and an aldehyde … on the same
carbon.
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17.1 Carboxylic Acids
methanoic acid
(common name: formic acid)
CH3CO2H
ethanoic acid
(common name: acetic acid)
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17.3 Acidity of Carboxylic Acids
Carboxylic acids are weak acids
(ethanoic acid)
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17.1 Carboxylic Acids
► Carboxylic acids
►Suffix: -oic acid
►No need to number the acid group… it
has to be on an end carbon, so it is
automatically “1-”
propanoic acid
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End of Chapter 17
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It may be hard to believe,
but…
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