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APPLIED CHEMISTRY INHALATION AGENTS

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... exhibit isomerism is butane with 2 isomers: Mark Welliver. Slide 2006 ... Isomer B has three carbons in a chain and the fourth carbon branching off the centre. ... – PowerPoint PPT presentation

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Title: APPLIED CHEMISTRY INHALATION AGENTS


1
APPLIED CHEMISTRY INHALATION AGENTS
Mark Welliver CRNA MS
Mark Welliver Slide 2006
2
Outline
  • IUPAC nomenclature rules
  • Functional groups
  • Alkanes, Alkene, Alkynes
  • Ethers
  • Carboxyls
  • Alcohols
  • Aldehydes
  • Amines
  • Ketones

Mark Welliver Slide 2006
3
Inhaled Anesthetic Agents
Mark Welliver Slide 2006
4
Volatile Anesthetics Halogenated
Alkane Halothane (Fluothane) 2-bromo-2-chloro-1,
1,1-trifluoro-ethane Halogenated Hydrocarbons
(methyl ethyl ethers) Enflurane (Ethrane)
2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether Isoflurane (Forane)
1-chloro-2,2,2-trifluoroethyl difluoromethyl
ether Desflurane (Suprane) 1,2,2,2-tetrafluoro
ethyl difluoromethyl ether Sevoflurane
(Ultane) fluromethyl 1,1,1,3,3,3,-hexa-fluoro- i
sopropyl ether or fluoromethyl
2,2,2-trifluoro-1-(trifluoromethyl) ethyl
ether Non-Volatile Anesthetic Inorganic
Gas Nitrous Oxide-N2O
Mark Welliver Slide 2006
5
Chemical Structure of Inhalation Agents
H
Mark Welliver Slide 2006
6
IUPAC Nomenclature
  • The IUPAC name for an organic compound contains
    these two parts
  • 1) a root indicating how many carbon atoms are in
    the longest continuous chain of carbon atoms
  • 2) a prefix and/or a suffix to indicate the
    family or functional group to which the compound
    belongs.

Mark Welliver Slide 2006
7
Root Names
memorize!
Mark Welliver Slide 2006
8
Functional Groups
Mark Welliver Slide 2006
9
Hydrocarbons
  • Volatile anesthetics are hydrocarbons
  • And they contain halogens, F-,Cl-, Br-
  • They are Halogenated hydrocarbons
  • Two main categories
  • 1) Alkanes
  • 2) Ethers

Mark Welliver Slide 2006
10
Alkanes
  • Alkanes are single-chained hydrocarbons
  • Alkenes are double bonded C C
  • Alkynes are triple bonded C C
  • Halogenated Alkane- Halogens added F,CL, Br

C-C
ethane
Mark Welliver Slide 2006
11
Nomenclature-Alkanes
  • The smallest alkane to exhibit isomerism is
    butane with 2 isomers

Mark Welliver Slide 2006
12
  • Isomer A has the four carbons in a chain and so
    is butane

Mark Welliver Slide 2006
13
  • Isomer B has three carbons in a chain and the
    fourth carbon branching off the centre. To name
    compounds such as this one, with branches, the
    IUPAC system
  • chooses a root name to indicate the longest
    continuous chain of carbons, in this case prop
    for the three carbons.
  • name the branch.

Mark Welliver Slide 2006
14
  • Name the Branch
  • - using the root name for the longest continuous
    chain of
  • carbons in the branch (in this case meth for
    the one
  • carbon)
  • -followed by -yl to indicate that this number of
    carbons is
  • in a branch.
  • put the three parts of the name (branch root
    family)
  • together to form the compounds name, with the
    branch
  • names prefixing the root, and the family name
    taking its
  • usual form.
  • Following these steps, compound B is named
  • methylpropane

Mark Welliver Slide 2006
15
Alkane Nomenclature
  • 1.) Count the longest carbon chain
  • If the carbon chain is
  • 1 carbon named "methane"
  • 2 carbons named "ethane"
  • 3 carbons named "propane"
  • 4 carbons named "butane"
  • 5 carbons named "pentane"
  • 6 carbons named "hexane"
  • 7 carbons named "heptane"
  • 8 carbons named "octane"
  • 9 carbons named "nonane"
  • 10 carbons named "decane"

Mark Welliver Slide 2006
16
Alkane Nomenclature
  • 2.) Number the carbon chain, starting with the
    end closest to the substituent. Always try to get
    the lowest number possible.
  • If there are two substituents, name the carbon
    chain so that it has the lowest possible number

C
C
1
3
5
C-C-C-C-C-C
2
4
6
6
5
4
3
2
1
Would this compound be numbered from the left or
right? The answer is that it would be answered
from the right. If the molecule was named from
the  left, you would have substituents on carbons
3 and 5. Numbering from the right, the
subsituents are on carbons 2 and 4.
Mark Welliver Slide 2006
17
Alkane Nomenclature
  • 3.) Name and number the substituent keep
    substituents alphabetical

Mark Welliver Slide 2006
18
Alkane Nomenclature
  • 3.) Name and number the substituent

2,4 di methyl hexane
2 methyl hexane
2,3 di methyl hexane
3 ethyl, 2,4 di methyl hexane
Mark Welliver Slide 2006
19
Name the following
Mark Welliver Slide 2006
20
Halogenated Alkanes
  • Halogens added F,Cl, Br
  • Halothane
  • The only halogenated alkane anesthetic in use
  • Name the above compound
  • 2-bromo-2-chloro-1,1,1-trifluoro-ethane

F
Cl
-
-
Br-C-C-F
-
-
F
H
Mark Welliver Slide 2006
21
Halogenated Alkanes
  • Halogens added F,Cl, Br
  • Halothane
  • The only halogenated alkane anesthetic in use,
    rare

F
Cl
-
-
Br-C-C-F
-
-
F
H
Mark Welliver Slide 2006
22
Alkane vs Ether
  • The C2H5 group is known as an ethyl- group.
  • However, the C2H5O group is known as the ethoxy-
    group. Below is a table with the most common oxy-
    groups you'll find.

Mark Welliver Slide 2006
23
Ethers R-O-R1
  • Two types of ethers
  • Cyclic
  • Acyclic

Mark Welliver Slide 2006
24
Ethers
  • Two groups acyclic cyclic
    (acyclic focus)
  • Ethers are R-O-R'. The RO- is called the alkoxy
    group
  • C-O-C basic ether building block
  • C-O -C

Alkane group
Alkoxy group
Mark Welliver Slide 2006
25
Nomenclature Ethers
  • C-O-C methoxy methane/ dimethyl ether
  • C-O-C-C methoxy ethane/ ethyl methyl ether
  • C-O-C-C-C methoxy propane/methyl propyl ether
  • Alphabetical or by size (smaller to longer)
  • Usually longest chain takes name

26
Nomenclature Ethers
  • H3C-O-C2H5 / C-O-C-C
  • Naming substituents in ethers
  • The longest parent chain is the ethane group.
    Thus the methyoxy- becomes the substituent group.
    Hence, the name of this molecule is
    methyoxyethane or methoxy ethane or
    ethyl methyl ether or methyl
    ethyl ether

Mark Welliver Slide 2006
27
Nomenclature- Halogenated Inhalation Ethers
  • Methyl (one carbon) ethyl (two carbon) ethers
    (R-O-R)
  • C -C-O-C

1
2
1
Ethyl group
Methyl group
R-O-R ether
Mark Welliver Slide 2006
28
Enflurane (Ethrane)
F
Cl
F
-
-
-
  • -C-C-O-C-

H
H
1
2
1
-
-
-
F
F
F
2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether 1,1difluro methoxy 1,1,2, trifluro 2 chloro
ethane
Enflurane (Ethrane)
Mark Welliver Slide 2006
29
Nomenclature- Inhalation Ethers
  • Methyl (one carbon) ethyl (two carbon) ethers
    (R-O-R)
  • Isoflurane (Forane) 1-chloro-2,2,2-trifluoroethyl
    difluoromethyl ether
  • C -C-O-C

1
2
1
Ethyl group
Methyl group
R-O-R ether
Mark Welliver Slide 2006
30
Isoflurane / Flurane
Cl
F
F
-
-
-
  • -C-C-O-C-

H
F
1
2
1
-
-
-
F
H
F
1-chloro-2,2,2-tetrafluoroethyl difluoromethyl
ether 1,1difluro methoxy 1 chloro- 2,2,2,
trifluro ethane
Isoflurane (Forane)
Mark Welliver Slide 2006
31
Desflurane / Suprane
F
F
F
-
-
-
  • -C-C-O-C-

1
H
2
1
F
-
-
-
F
H
F
1,2,2,2 tetrafluro ethyl difluoro methyl
ether 1,1difluro methoxy 1,2,2,2, tetrafluro
ethane
Mark Welliver Slide 2006
32
Sevoflurane / Ultane
Mark Welliver Slide 2006
F
-
F
-F
F-
C
-
  • -C-O-C-

H
H
-
-
-C-
H
F
F
-
F
fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)
ethyl ether fluromethyl 1,1,1,3,3,3, hexafluoro
isopropyl ether 1, fluoro methoxy 1,1,1 trifluoro
methyl 2,2,2 trifluoro ethane
33
Volatile Anesthetics Halogenated
Alkane Halothane (Fluothane) 2-bromo-2-chloro-1,1
,1-trifluoro-ethane Enflurane (Ethrane)
2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether Isoflurane (Forane) 1-chloro-2,2,2-triflu
oroethyl difluoromethyl ether Desflurane
(Suprane) 1,2,2,2-tetrafluoroethyl difluoromethyl
ether Sevoflurane (Ultane) fluromethyl
1,1,1,3,3,3,-hexa-fluoro-isopropyl ether or
fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)
ethyl ether Non-Volatile Anesthetic Inorganic
Gas Nitrous Oxide-N2O
Mark Welliver Slide 2006
34
Ethers
  • - O - C2H5
  • The parent chain will be the cyclohexane group.
    We have an ethyoxy group, so we get a
    ethyoxycyclohexane.

Mark Welliver Slide 2006
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