mcmurry organic chemistry 6th edition chapter 3 (c) 2003 2 representations of structural formulas...
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McMurry Organic Chemistry 6th edition Chapter 3 (c) 2003
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Representations of Structural Formulas
Dot formulas are more cumbersome to draw than dash formulas and condensed formulas
Lone-pair electrons are often (but not always) drawn in, especially when they are crucial to the chemistry being discussed
2.12 Drawing Chemical Structures
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Dash formulas Each dash represents a pair of electrons This type of representation is meant to
emphasize connectivity and does not represent the 3-dimensional nature of the molecule
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Condensed structures: C-H and C-C and single bonds aren't shown but understood If C has 3 H’s bonded to it, write CH3
If C has 2 H’s bonded to it, write CH2; and so on. The compound called 2-methylbutane, for example, is written as follows:
Horizontal bonds between carbons aren't shown in condensed structures—the CH3, CH2, and CH units are simply but vertical bonds are added for clarity
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Condensed Structural Formulas In these representations, some or all of the dash lines are omitted
In partially condensed structures all hydrogens attached to an atom are simply written after it but some or all of the other bonds are explicitly shown
In fully condensed structure all bonds are omitted and atoms attached to carbon are written immediately after it
For emphasis, branching groups are often written using vertical lines to connect them to the main chain
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Three-Dimensional Formulas
The conventions for this are: Bonds that lie in the plane of the paper are indicated
by a simple line Bonds that come forward out of the plane of the
paper are indicated by a solid wedge Bonds that go back out of the plane of the paper are
indicated by a dashed wedge
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Classes of Compounds
Classification based on functional group Three broad classes
Hydrocarbons Compounds containing oxygen Compounds containing nitrogen
=>
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Hydrocarbons
Alkane: single bonds, sp3 carbons Cycloalkane: carbons form a ring Alkene: double bond, sp2 carbons Cycloalkene: double bond in ring Alkyne: triple bond, sp carbons Aromatic: contains a benzene ring
=>
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Compounds Containing Oxygen
Alcohol: R-OH Ether: R-O-R' Aldehyde: RCHO
Ketone: RCOR'
CH3CH2 C
O
H
CH3 C
O
CH3
=>
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Cyclic ethers and ketones
OO
THF
(tetrahydrofuran)cyclopentanone
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Carboxylic Acids and Their Derivatives
Carboxylic Acid: RCOOH Acid Chloride: RCOCl Ester: RCOOR' Amide: RCONH2
C
O
OH
C
O
Cl
C
O
OCH3C
O
NH2
=>
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Cyclic esters
O
O
O
O
Cyclic ester (cyclic ether and cyclic ketone)
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Compounds Containing Nitrogen
Amines: RNH2, RNHR', or R3N
Amides: RCONH2, RCONHR, RCONR2
Nitrile: RCN
N
O
CH3
CH3 C N
=>
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Summary of Important Families of Organic Compounds
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Summary (cont.)
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3.2 Alkanes and Alkane Isomers
Alkanes: Compounds with C-C single bonds and C-H bonds only (no functional groups)
The formula for an alkane with no rings in it must be CnH2n+2 where the number of C’s is n
Alkanes are saturated with hydrogen (no more can be added
They are also called aliphatic compounds
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Alkane Isomers
CH4 = methane, C2H6 = ethane, C3H8= propane
The molecular formula of an alkane with more than three carbons can give more than one structure C4 (butane) = butane and isobutane
C5 (pentane) = pentane, 2-methylbutane, and 2,2-dimethylpropane
Alkanes with C’s connected to no more than 2 other C’s are straight-chain or normal alkanes
Alkanes with one or more C’s connected to 3 or 4 C’s are branched-chain alkanes
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Constitutional Isomers
Isomers that differ in how their atoms are arranged in chains are called constitutional isomers
They must have the same molecular formula to be isomers
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3.4 Naming Alkanes
Compounds are given systematic names by a process that uses Prefix-Parent-Suffix
Follows specific rules Named as longest possible chain Carbons in that chain are numbered in sequence substituents are numbered at their point of attachment Compound name is one word (German style) Complex substituents are named as compounds would
be
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Names of Small Hydrocarbons
No. of Carbons Formula Name (CnH2n+2)
1 Methane CH4
2 Ethane C2H6
3 Propane C3H8
4 Butane C4H10
5 Pentane C5H12
6 Hexane C6H14
7 Heptane C7H16
8 Octane C8H18
9 Nonane C9H20
10 Decane C10H22
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Nomenclature of Branched-Chain Alkanes (IUPAC) Locate the longest continuous chain of carbons; this is the parent chain and
determines the parent name.
Number the longest chain beginning with the end of the chain nearer the substituent Designate the location of the substituent
When two or more substituents are present, give each substituent a number corresponding to its location on the longest chain
Substituents are listed alphabetically
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When two or more substituents are identical, use the prefixes di-, tri-, tetra- etc.
Commas are used to separate numbers from each other The prefixes are used in alphabetical prioritization
When two chains of equal length compete to be parent, choose the chain
with the greatest number of substituents
When branching first occurs at an equal distance from either end of the parent chain, choose the name that gives the lower number at the first point of difference
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3.3 Alkyl Groups
Alkyl group – remove one H from an alkane (a part of a structure)
Naming: replace -ane ending of alkane with -yl ending CH3 is “methyl” (from methane)
CH2CH3 is “ethyl” from ethane
See Table 3.4 for a list
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Physical Properties
Boiling points and melting points increase as size of alkane increases
Forces between molecules (temporary dipoles, dispersion) are weak
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3.6 Cycloalkanes
Cycloalkanes are alkanes that have carbon atoms that form a ring (called alicyclic compounds)
Simple cycloalkanes rings of CH2 units, (CH2)n, or CnH2n
Structure is shown as a regular polygon with the number of vertices equal to the number of C’s (a projection of the actual structure)
cyclopropanecyclohexanecyclopentane
cyclobutane
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Complex Cycloalkanes
Naturally occurring materials contain cycloalkane structures Examples: chrysanthemic acid (cyclopropane),
prostaglandins (cyclopentane), steroids (cyclohexanes and cyclopentane)
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6. Alkenes: Structure and Reactivity
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Alkene - Hydrocarbon With Carbon-Carbon Double Bond Also called an olefin but alkene is better Includes many naturally occurring materials
Flavors, fragrances, vitamins
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6.3 Naming of Alkenes Find longest continuous carbon chain containing the double
bond and name the compound using the suffix “ene” Number carbons in chain so that double bond carbons have
lowest possible numbers Rings have “cyclo” prefix
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Names of Small Alkene
No. of Carbons Formula Name (CnH2n)
1
2 Ethene C2H4
3 Propene C3H6
4 Butene C4H8
5 Pentene C5H10
6 Hexene C6H12
7 Heptene C7H14
8 Octene C8H16
9 Nonene C9H18
10 Decene C10H20
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Many Alkenes Are Known by Common Names Ethylene = ethene Propylene = propene Isobutylene = 2-
methylpropene Isoprene = 2-methyl-1,3-
butadiene
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6.3 Degree of Unsaturation
Relates molecular formula to possible structures Degree of unsaturation: number of multiple bonds or rings Formula for saturated a acyclic compound is CnH2n+2
Each ring or multiple bond replaces 2 H's
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Example: C6H10
Saturated is C6H14
Therefore 4 H's are not present
This has two degrees of unsaturation Two double bonds? or triple bond? or two rings or ring and double
bond
H3CC
CC
CCH3
H H
H H
H H
H H
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Degree of Unsaturation With Other Elements Organohalogens (X: F, Cl, Br, I)
Halogen replaces hydrogen C4H6Br2 and C4H8 have one degree of unsaturation Oxygen atoms - if connected by single bonds
These don't affect the total count of H's
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Compounds with the same degree of unsaturation can have many things in common and still be very different
Degree of Unsaturation and Variation
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If C-N Bonds Are Present
Nitrogen has three bonds So if it connects where H was, it adds a connection
point Subtract one H for equivalent degree of unsaturation in
hydrocarbon
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Count pairs of H's below CnH2n+2 Add number of halogens to number of H's (X equivalent to
H) Don't count oxygens (oxygen links H) Subtract N's - they have two connections
Summary - Degree of Unsaturation
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6.4 Cis-Trans Isomerism in Alkenes
The presence of a carbon-carbon double can create two possible structures cis isomer - two similar
groups on same side of the double bond
trans isomer similar groups on opposite sides
Each carbon must have two different groups for these isomers to occur
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Cis, Trans Isomers Require That End Groups Must Differ in Pairs
180°rotation superposes Bottom pair cannot be
superposed without breaking C=C
X
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6.6 Sequence Rules: The E,Z Designation Neither compound is
clearly “cis” or “trans” Substituents on C1 are
different than those on C2
We need to define “similarity” in a precise way to distinguish the two stereoisomers
Cis, trans nomenclature only works for disubstituted double bonds
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Develop a System for Comparison of Priority of Substituents
Assume a valuation system If Br has a higher
“value” than Cl If CH3 is higher than H
Then, in A, the higher value groups are on opposite sides
In B, they are on the same side Requires a universally
accepted “valuation”
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E,Z Stereochemical Nomenclature Priority rules of Cahn,
Ingold, and Prelog The Cahn-Ingold-Prelog
convention is used to assign the groups of highest priority on each carbon
Compare where higher priority group is with respect to bond and designate as prefix
E -entgegen, opposite sides
Z - zusammen, together on the same side
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Ranking Priorities: Cahn-Ingold-Prelog Rules Must rank atoms that are connected at comparison point Higher atomic number gets higher priority
Br > Cl > O > N > C > H
In this case,The higher priority groups are opposite:(E )-2-bromo-2-chloro-propene
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If atomic numbers are the same, compare at next connection point at same distance
Compare until something has higher atomic number Do not combine – always compare
Extended Comparison
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Substituent is drawn with connections shown and no double or triple bonds
Added atoms are valued with 0 ligands themselves
Dealing With Multiple Bonds