1. Chapter 10 – Organic Chemistry
CHM1111 Section 04
Instructor: Dr. Jules Carlson
Thursday, December 1st

2. Organic Chemistry
There is no way we will be able to cover all of the content of these slides in detail in one lecture.
I encourage you all to read your textbook where it is all in greater detail.
The plan for this lecture is to give a flavour of the three things important to organic chemistry:
Naming the multitude (millions) of organic compounds
Understanding the importance (and naming) of different types of isomers
Understanding the basics of reaction chemistry and some of the types of reactions that take place

3. Alkanes, Alkenes, Alkynes
Number of Carbons
Prefix 1
Meth- 2
Eth- 3
Prop- 4
But- 5
Pent- 6
Hex- 7
Hept- 8
Oct- 9
Non- 10
Dec-
Hydrocarbon chains
Alkanes – all single bonds (CnH2n+2)
Alkenes – one double bond (CnH2n)
Alkynes – one triple bond (CnH2n-2)

4. Alkyl Chains
Butane
Isobutane
Pentane
Isopentane
Neopentane

5. Naming Branched-Chain Alkanes
Locate the longest continuous chain of carbon atoms.
Number the longest chain beginning with the end nearest the substituent.
Number the substituent groups accordingly.

6. Naming Alkenes/Alkynes
2,4-dimethyl-5-heptene
3-ethyl,3-methyl-4-hexyne
1-ethyl,4-methyl-2-cyclohexene

7. Other Alkyl Groups

8. Structure of Benzene

9.  Bonding in Benzene
Electron Delocalization

10. Some Substituents Substituent Group Name -Cl chloro -Br bromo -F
fluoro -I
iodo
-NH2
amino
-NO2
nitro
-OH
hydroxy
2-chloro-2-methyl-3-bromobutane

11. Ortho, Meta, and Para Substitution
Ortho – groups are on adjacent carbons
Meta – groups on carbons with one carbon between
Para – groups on carbons on opposite sides

12. Naming Aromatic Compounds

13. Functional Groups – Halogens Alkyl Halides
Alkyl Halides have the structure R-X, where X = F, Cl, Br, I

14. Functional Groups – Hydroxide Alcohols
Ethanol – 2 carbon chain with an alcohol
Take name, remove –ne, and add -ol
Alcohols can perform H-bonding and alcohols with shorter chains are polar

15. Secondary and Tertiary Alcohols

16. Naming Alcohols

17. Functional Groups with O - Ethers
Ethers have the formula R-O-R’
Ethyl isopropyl ether

18. Functional Groups – Amino
Amines

19. Functional Groups with O - Carbonyl Group
Appears in five common functional groups:
Aldehydes, Ketones, Carboxylic Acids, Esters and Amides
Aldehydes – Carbonyl is on a Terminal Carbon
Gains suffix - al
Ketones – Carbonyl is on a Central Carbon
Gains suffix -one
Carboylic Acids – Carbonyl + an alcohol group
Gains suffix –oic acid
Esters – Carbonyl + an ether group
Named first chain –yl, second chain -oate
Amides – Carbonyl + an amine group
Gains suffix - amide

20. Aldehydes and Ketones

21. Carboxylic Acids

22. Esters

23. Functional Groups with N- Nitriles
Have the formula R≡N Add the suffix -nitrile

24. Functional Group Summary
Chemistry, Canadian Edition ©2010 John Wiley & Sons Canada, Ltd.

25. Functional Group Summary – cont’d
Chemistry, Canadian Edition ©2010 John Wiley & Sons Canada, Ltd.

26. Stereoisomers
Stereochemistry – the study of arrangements of atoms in molecules
Isomers – have same atoms but connections are different. (ex. Propanol and Acetone)
Stereoisomers – have atoms connected in the same way but differ in arrangement in space
Stereroisomer
MP (⁰C)
BP (⁰C)
cis-
-81 60
trans-
-49 48

27. The E/Z System
List the groups bound directly to the C=C double bond. In this case, they are –H, -Br, -Cl and –CH3.
Order them according to priority (higher molecular weight = higher priority) on each C atom. Here, Br > Cl and CH3 > H.
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

28. Chirality
Your hands are enantiomers – they are mirror images of each other

29. 2-pentanol These are therefore enantiomers!

30. Chirality
For a molecule to be chiral, the Carbon must be bonded to 4 different groups
There is an R/S system that names compounds based on orientation based on priorities, Place H behind the page, if
1-2 goes right, it is R, 1-2 goes left it is S.

31. The R/S System
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.
Chemistry, Canadian Edition ©2010 John Wiley & Sons Canada, Ltd.

32. The R/S System The inactive enantiomer of Ibuprofen
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.

33. Reactions Types of Reactions:
Substitution – Replace one atom or group with another
Elimination – Remove an atom(s) from the molecule, produces an unsaturation (double bond between C)
Addition – Adding atoms to a double bond

34. Reactions and Electron Density
Nucleophile – Reagents seeking a positive charge. They have a negative charge, a lone pair of electrons or both
Electrophile – Reagents seeking a negative charge. They have a positive charge or a partial positive charge.
For nucleophilic substitution reactions:
Textbook talks about 1-step and 2-step mechanisms, rates of reaction, quality of nucleophiles and leaving groups.

35. Substitution Reactions
Some examples…

36. Elimination Reactions
Examples:
Chemistry, Canadian Edition ©2010 John Wiley & Sons Canada, Ltd.

37. More Addition Reactions

38. Addition Reactions
Things get added across a double bond, e.g. by hydrogenation:

39. Catalysis of Addition Reactions