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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.
10.1 Hydrocarbons
Learning objective:
Draw and naming hydrocarbons using the IUPAC system
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
Alkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Alkane Isomers
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
IsobutaneButane
Pentane Isopentane Neopentane
Alkyl Groups
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
Naming Branched-Chain Alkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10 – 1 Naming Alkanes
Name the following alkanes:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
Cycloalkanes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Common Substituents
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Alkenes
CnH2n
Unsaturated (contain at least one C-C double bond)
ethene, propene, butene, …
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
Naming Alkenes and Alkynes
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
10.2 Aromatic Compounds
Learning objective:
Draw and name aromatic compounds using the IUPAC system
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Structure of Benzene
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Bonding in Benzene
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Naming Benzene Compounds
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10-3 Naming Benzene Compounds
Name the following compounds:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
10.3 Functional Groups
Learning objective:
Drawing and naming compounds containing common functional groups.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Functional Groups
Alkyl HalidesAlcohols
EthersAmines
AldehydesKetones
Carboxylic AcidsEsters
AmidesNitriles
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Alkyl Halides
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Alcohols H-bond, as does water
Primary Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Secondary Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Tertiary Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Naming Alcohols
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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
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.
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
Example 10 – 6 Ethers
Write line structures for (a) diethyl ether, (b) ethyl propyl ether, and (c) ethyl isopropyl ether.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Amines
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Amines
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10 – 7 Amines
Name the following amines and classify each as primary, secondary, or tertiary:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
The Carbonyl Group
Appears in five common functional groups:Aldehydes, Ketones, Carboxylic Acids, Esters and Amides
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Aldehydes and Ketones
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Aldehydes and Ketones
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10 – 8 Aldehydes and Ketones
Give IUPAC names for the following compounds:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Carboxylic Acids
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Carboxylic Acids
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Carboxylic Acids
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Esters
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Amides
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Nitriles
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Functional Group Summary
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Functional Group Summary – cont’d
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
10.4 Stereochemistry
Learning objective:
Recognizing, naming and drawing stereoisomers.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
10.4 Stereochemistry
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
These are different molecules!
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
Example 10 – 10 E/Z Stereoisomers
Draw and name the two stereoisomers of 1-bromo-3-chloro-4-isopropyl-3-heptene.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Learn to Draw in Three Dimensions!
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Conformations
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Drawing a Newman Projection
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10-11 Drawing Newman Projections
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10-12 Drawing a Line Structure from a Newman Projection
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Potential Energy During a Rotation
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Enantiomers
Your hands are enantiomers – non-superimposable mirror images of one another
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Chirality
2-pentanol
These are therefore enantiomers!Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Chirality
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Example 10 – 13 Chiral Compounds
Two amino acids are glycine and leucine. Determine whether each of these compounds is chiral or achiral.
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
The R/S System for Naming Chiral Compounds
Chirality may determine the activity of a molecule!
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
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.
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
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:
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Chapter 10 Visual Summary
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Chapter 10 Visual Summary
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Chapter 10 Visual Summary
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.
Chapter 10 Visual Summary
Chemistry, 2nd Canadian Edition ©2013 John Wiley & Sons Canada, Ltd.