10.1 hydrocarbons 10.2 aromatic compounds 10.3 functional groups 10.4 stereochemistry chapter 10....
TRANSCRIPT
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10.1 Hydrocarbons
10.2 Aromatic Compounds
10.3 Functional Groups
10.4 Stereochemistry
Chapter 10. Organic Chemistry - Structure
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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10.1 Hydrocarbons
Learning objective:
Draw and naming hydrocarbons using the IUPAC system
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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10.1 Hydrocarbons
Alkanes
CnH2n+2
saturated (single C-C bonds only)
methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Alkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Alkane Isomers
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
IsobutaneButane
Pentane Isopentane Neopentane
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Alkyl Groups
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Naming Branched-Chain Alkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
1. Locate the longest continuous chain of carbon atoms.2. Number the longest chain beginning with the end
nearest the substituent.3. Number the substituent groups accordingly.
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Naming Branched-Chain Alkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Example 10 – 1 Naming Alkanes
Name the following alkanes:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Example 10 – 2 Drawing Alkanes
Draw line structures of the following alkanes: (a) 2,3,6-trimethyloctane; (b) 5-ethyl-2-methyl-5-propylnonane; and (c) 2-methylbutane.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Cycloalkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Common Substituents
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Alkenes
CnH2n
Unsaturated (contain at least one C-C double bond)
ethene, propene, butene, …
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Alkynes
CnH2n-2
Unsaturated (contain at least one C-C triple bond)
ethyne, propyne, butyne, …
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Naming Alkenes and Alkynes
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10.2 Aromatic Compounds
Learning objective:
Draw and name aromatic compounds using the IUPAC system
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Structure of Benzene
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Bonding in Benzene
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Naming Benzene Compounds
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Example 10-3 Naming Benzene Compounds
Name the following compounds:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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10.3 Functional Groups
Learning objective:
Drawing and naming compounds containing common functional groups.
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Functional Groups
Alkyl HalidesAlcohols
EthersAmines
AldehydesKetones
Carboxylic AcidsEsters
AmidesNitriles
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Alkyl Halides
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Example 10 – 4 Alkyl Halides
Draw line structures and give the IUPAC names for all of the structural isomers of C4H9Br. State whether each is a primary, secondary, or tertiary alkyl halide.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Alcohols H-bond, as does water
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Primary Alcohols
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Secondary Alcohols
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Tertiary Alcohols
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Naming Alcohols
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Synthesizing Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
o
2 3
400 C2 3ZnO/Cr O catalystCO 2H CH OH
Yeast6 12 6 2 5 2C H O 2C H OH 2CO
Acid3 2 2 CatalystCH CH = CH + H O CH3CH=CH2
OH
Propene Isopropanol
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Example 10 – 5 Alcohols
Write line structures for each of the following, and state whether each is a primary, secondary, or tertiary alcohol:
(a) 3-pentanol; (b) 2-methyl-2-butanol; and (c) 1-hexanol.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Ethers
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
2 4H SO2R OH HO R R O R H O
2 4H SO3 2 3 2 2 3CH CH OH CH CH O CH CH
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Example 10 – 6 Ethers
Write line structures for (a) diethyl ether, (b) ethyl propyl ether, and (c) ethyl isopropyl ether.
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Amines
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Amines
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Example 10 – 7 Amines
Name the following amines and classify each as primary, secondary, or tertiary:
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The Carbonyl Group
Appears in five common functional groups:Aldehydes, Ketones, Carboxylic Acids, Esters and Amides
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Aldehydes and Ketones
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Aldehydes and Ketones
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Example 10 – 8 Aldehydes and Ketones
Give IUPAC names for the following compounds:
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Carboxylic Acids
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Carboxylic Acids
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Carboxylic Acids
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Esters
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Amides
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Example 10 – 9 Carboxylic Acids, Esters, and Amides
Draw the following compounds: (a) hexanoic acid; (b) 2-ethyl butanoic acid; (c) methyl propanoate, (d) phenyl ethanoate; (e) N-ethylethanamide (N-ethylacetamide); and (f) N-methyl-N-phenylpropanamide.
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Nitriles
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Functional Group Summary
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Functional Group Summary – cont’d
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10.4 Stereochemistry
Learning objective:
Recognizing, naming and drawing stereoisomers.
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10.4 Stereochemistry
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
These are different molecules!
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Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
1. List the groups bound directly to the C=C double bond. In this case, they are –H, -Br, -Cl and –CH3.
2. Order them according to priority (higher molecular weight = higher priority) on each C atom. Here, Br > Cl and CH3 > H.
3. Look at the highest priority ones (Br, CH3). If they are cis to one another, it is Z. If they are trans, it is E. This one is therefore (E)-1-bromo-1-chloropropene
The E/Z System
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Example 10 – 10 E/Z Stereoisomers
Draw and name the two stereoisomers of 1-bromo-3-chloro-4-isopropyl-3-heptene.
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Learn to Draw in Three Dimensions!
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Conformations
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Drawing a Newman Projection
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Example 10-11 Drawing Newman Projections
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Example 10-12 Drawing a Line Structure from a Newman Projection
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Potential Energy During a Rotation
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Enantiomers
Your hands are enantiomers – non-superimposable mirror images of one another
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Chirality
2-pentanol
These are therefore enantiomers!Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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Chirality
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Example 10 – 13 Chiral Compounds
Two amino acids are glycine and leucine. Determine whether each of these compounds is chiral or achiral.
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The R/S System for Naming Chiral Compounds
Chirality may determine the activity of a molecule!
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The R/S System
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
1. Locate the chirality centre, identify the four groups attached to it, and assign priorities to them just as we did for the E/Z configurations of cis–trans stereoisomers.
2. Orient the molecule so that the group having the lowest priority is pointing away from you.
3. Read the other three groups (pointing toward you) from highest to lowest priority. If these are in a clockwise direction, the molecule is the R enantiomer. If they are in the counter-clockwise direction, it is the S enantiomer.
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The R/S System
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
The groups attached to the chirality centre in increasing priority are - H, -CH3, -C6H4 and COOH. The other three groups from highest to lowest priority are - COOH, -C6H4 and -CH3.These three groups are in a clockwise order, and so this is the (R)-ibuprofen, and the active enantiomer must be (S)-ibuprofen.
The inactive enantiomer of Ibuprofen
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Example 10 – 14 Identifying R and S Enantiomers
Assign an R or S configuration to the chirality centre in the enantiomer of 3,3-dimethylcyclohexanol shown:
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Chapter 10 Visual Summary
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Chapter 10 Visual Summary
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Chapter 10 Visual Summary
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Chapter 10 Visual Summary
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.