1. Chapter 10 Organic Chemistry
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2. 10.1 Why Carbon Is Different
Electron configuration: [He]2s22p2 effectively prohibits ion formation
Small atomic radius gives rise to short, strong CC bonds and stable compounds
Hybridized atoms (sp- and sp2-) can form strong p bonds with unhybridzed p orbitals
Catenation to form chains and rings containing single, double and triple bonds.
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Examples of Single and Multiple Bonds
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Carbon’s lack of d electrons enhances stability
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Examples of catenation
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6. 10.2 Classes of Organic Compounds
The seemingly limitless variety of organic compounds results from:
Carbon’s ability to form chains by bonding to itself
Presence of elements other than carbon and hydrogen
Functional groups – a group of atoms that determines many of a molecule’s properties
Multiple bonds
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8. How are Organic Compounds Named?
Alkanes
Identify the longest continuous carbon chain to get the parent name.
Number the carbons in the continuous chain, beginning at the end closest to the substituent.
Identify the substituent and use a number and a prefix to specify location and identity, respectively.
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9. Name the compound shown below.
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3,3-dimethylhexane
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Examples of functional groups
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Examples of alcohols
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Electrostatic maps of selected functional groups
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15. Naming Specific Functional Groups
Alcohols
Identify the longest chain that includes the –OH group.
Change the –e ending to -ol.
Number to give the –OH the lowest number.
When the chain also contains an alkyl substituent, give the –OH the lowest number.
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Carboxylic Acids
Identify the longest chain that includes the carboxyl group.
Change the –e ending to –oic acid.
Number starting with the carbonyl (C=O) carbon.
Use numbers and prefixes to indicate the position and identity of any substituents.
Esters
Name as derivatives of carboxylic acids by replacing the –ic acid ending with -oate.
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Aldehydes
Identify the longest chain that includes the carbonyl group.
Change the –e ending to -al.
Number starting with the carbonyl (C=O) carbon.
Use numbers and prefixes to indicate the position and identity of any substituents.
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Ketones
Identify the longest chain that includes the carbonyl group.
Change the –e ending to -one.
Number to give the carbonyl group the lowest possible number.
Use numbers and prefixes to indicate the position and identity of any substituents.
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Primary Amines
Identify the longest chain that includes the –NH2 group.
Change the –e ending to -amine.
Number starting with the carbon to which the –NH2 group is bonded.
Use numbers and prefixes to indicate the position and identity of any substituents.
Primary Amides
Can be named as derivatives of carboxylic acids.
Or, by replacing the –e ending with –amide.
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20. Compounds with More Than One Substituent
Prefixes of di, tri, tetra, penta and so forth are used to denote the number of substituents.
Substituent names are alphabetized.
Numbers are used to indicate position of the alphabetized substituents.
Prefixes are not used in alphabetization.
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21. Name the following compounds.
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2-pentanone
3-methylbutanoic acid
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Identify the functional groups in the following compound.
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amine
ester
carboxylic acid
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25. 10.3 Representing Organic Molecules
Condensed structural formula (Condensed Structure): shows the same information as a structural formula but in condensed form.
CH3(CH2)6CH3
Kekulé structures: similar to Lewis structure but without showing lone pairs
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Skeletal Structures:
Consist of straight lines that represent carbon-carbon bonds.
Heteroatoms (atoms other than carbon or hydrogen) are shown explicitly
Resonance: repositioning of electrons shown by curved arrows
NH2
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Write the molecular formula and a structural formula for the following. O
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CH3COCH2CH3
C4H8O
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Draw the resonance structures for ozone. O3
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10.4 Isomerism
Constitutional (structural) isomerism occurs when the same atoms can be connected in two or more different ways.
Stereisomerism occurs when atoms are bonded in identical ways but differ in the orientation of those bonds in space.
Geometrical Isomers
Optical Isomers
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Geometrical isomers occur in compounds
that have restricted rotation around a bond.
cis (same side)
trans (opposite side)
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Optical Isomers are nonsuperimposable mirror images of one another.
Such molecules are termed chiral.
A pair of such mirror-image molecules are called enantiomers.
An equimolar mixture of the enantiomers is called a racemic mixture.
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Bond designations to indicate stereochemistry
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38. Measurement of Optical Activity
Dextrorotatory – plane of polarization is rotated to the right.
Levorotatory – plane of polarization is rotated to the left.
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10.5 Organic Reactions
Important terms
Electrophile
– a species with a region of positive or partial positive charge
electron-poor
Nucleophile
a species with a region of negative or partial negative charge
electron-rich
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Addition Reactions
Reaction involving the addition of a molecule or an ion to another molecule
Electrophilic addition – adding species is an electrophile
Nucleophilic addition – adding species is a nucleophile
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41. Example: electrophilic addition
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Text Figure 1038
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44. Example: nucleophilic addition
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45. Comparison of electrophilic and nucleophilic addition
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46. Substitution Reactions
Reaction when one group is replaced by another.
Electrophilic substitution – an electrophile attacks an aromatic molecule and replaces a hydrogen atom
Nucleophilic substitution – a nucleophile replaces another group on a carbon atom
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47. Electrophilic Substitution Reaction
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49. Nucleophilic Substitution Reaction
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50. Comparison of electrophillic and nucleophillic substitution
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51. Other Types of Organic Reactions
Elimination – reaction in which a double bond forms and small molecule is removed
Oxidation-reduction – involve the loss and gain of electrons
Isomerization – one isomer is converted to another
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Examples
Elimination
Oxidation-reduction
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Isomerization
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Draw the mechanism for the nucleophilic addition of CN to CH3CHO.
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Draw the mechanism for the nucleophilic addition of CN to CH3CHO.
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10.6 Organic Polymers
Polymers – molecular compounds made up of many repeating units called monomers
Types
Addition polymers form when monomers join end to end
Condensation polymers form when two different functional groups combine in an elimination reaction
Often are copolymers which are made of two or more different monomers
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57. Addition polymerization
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59. Condensation polymerization
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60. Ester and Ether Formation by Condensation
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Biological Polymers
Naturally occurring polymers include
Proteins – polymers of amino acids
Polysaccharides – polymers of sugars
Nucleic acids – polymers of nucleotides
DNA (deoxyribonucleic acid)
RNA (ribonucleic acid)
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Protein formation
Peptide bonds are also called amide
linkages since they contain an amide
functional group.
Very long chains are called proteins while
shorter chains are called polypeptides.
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Carbohydrates with different linkages
b linkage
a linkage
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Structure of a nucleotide (found in DNA)
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Key Points
Unique features of carbon
Classes of organic compounds
Naming organic compounds
Isomerism
Constitutional isomerism
Stereoisomerism
Geometrical isomers
Optical isomers
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Key Points
Organic reactions
Addition reactions
Electrophilic addition
Nucleophilic addition
Substitution reactions
Electrophilic substitution
Nucleophilic substitution
Elimination reactions
Oxidation-reduction reactions
Isomerization reactions
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Key Points
Polymers
Addition
Condensation
Biological
Proteins
Carbohydrates
Nucleic Acids
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