Unit A: Organic Chemistry

1. Unit A: Organic Chemistry This PowerPoint is available on the Plone Site. It is your responsibility to print off the notes that you would like. You will not be able to write everything down in class as this will inhibit the time we have to spend on practicing concepts and performing labs.

2. Assessment • Homework will be taken in randomly • Even though homework may not be taken in every day, this does not mean you are not required to complete it fully. This is a 30-level course and the expectation is that you keep up with practicing concepts daily as we will continue to move forward each day. • 3 Quizzes will be given throughout the unit • You should use these to your advantage as they test smaller sections of the curriculum and help prepare you for the Unit Exam • Labs – one formal Stations Lab to be handed in • Unit Exam – test format will be given to you later

3. OrganicChemistry • Today’s Objectives: • Define organic compounds as compounds containing carbon, recognizing inorganic exceptions such as carbonates, cyanides and carbides • Identify and describe significant organic compounds in daily life, demonstrating generalized knowledge of their origins and applications • STS: Demonstrate an understanding that science and technology are developed to meet societal needs and expand human capability Unit A: Chapters 9 and 10

4. Organic Introduction • Today’s Agenda: • Introduce organic chemistry and review the origins and applications of some major organic compounds • “Carbon – The element of life” video Section 9.1 (pg. 354-361)

5. What is Organic Chemistry? • The early definition related to compounds obtained only from living things. • Today, it is a major branch of chemistry that deals with compounds of carbon, called ORGANIC compounds*. • *Carbon compounds that are exceptions and considered INORGANIC are compounds like: • Oxides carbon monoxide (CO(g) ) and carbon dioxide (CO2(g) ), and • Ionic compounds of carbon-based ions, such as carbonate CO32-, cyanide CN-, and carbide ions, SiC (silicon carbide) • The major source of carbon compounds is still living or previously living things, such as plants, animals and all types of fossil fuels.

6. Organic or Inorganic??

7. Why is carbon special? • There are millions or organic compounds and only a thousand inorganic compounds. WHY? • Carbon has a bonding capacity of 4 • Remember Lewis Dot Diagrams from Chem 20?? • This means carbon can bond extensively and can bond together to form chains effectively = called Polymerism • Carbon covalently bonds by sharing 4 pairs of electrons. These bonds may be single, double or triple, all producing stable compounds • Compounds can form with same number of each type of atom but different structures = Isomerism

8. Determining Lewis Formulas • So why do we care about bonding capacity? • If we know how many bonding e-’s an atom has, we can predict what structure a molecular compound will have H I.e. Carbon can form 4 single bonds, 2 double bonds, 1 triple and 1 single, or 1 double and 2 singles

9. Polymers • Examples of repeating carbon chains:

10. Isomers • Compounds with the same number of each type of atom but different structures (C4H10) • We will talk about this in more detail later

11. Importance of Organic Chemistry • Building units of all living matter: carbohydrates, proteins, fats • All foods are organic compounds • Photosynthesis is a reaction that makes carbon a part of our food. Carbon is passed along through food chains and sugar from photosynthesis is modified and combined with other materials. • Dead organisms are food for other organisms, or are buried in the earth and converted to fossil fuels like peat, coal and petroleum • Petroleum is the source of fuel and starting material for plastics, fabrics and industrial chemicals

12. The carbon cycle is an illustration of the interrelationship of all living things with the environment and with technologies that refine and use fossil fuels We will continually outline the importance of organic compounds in our daily lives

13. Carbon: The Element of Life Complete the worksheet provided as you watch the following video (20 min)

15. Today’s homework • Ensure video worksheet is complete and in your notes to review later • Work on Are you Ready pg. 354-355 # 1- 6 – due tomorrow • What is coming up tomorrow? • Naming alkanes, branched alkanes and cycloalkanes

16. Naming Organic Compounds • Today’s Objectives: • Name and draw structural, condensed structural, and line diagrams and formulas for saturated and unsaturated aliphatic (including cyclic) • Containing up to 10 carbon atoms in the parent chain/cyclic structure • Containing only one type of a functional group or multiple bond • Using the IUPAC nomenclature guidelines • Identify types of compounds from the functional groups, given the structural formula • Define structural isomerism and relate to variations in properties Section 9.2 (pg. 366-374)

17. Four Types of Formulas • Molecular Formulas C5H12(g) Not very useful for organic compounds because so many isomers can exist • Structural Formulas • Condensed Structural Formulas • Line Diagrams – end of line segment represents carbon – it is assumed to satisfy each carbon’s octet

18. Naming Organic Compounds • Aliphatic Hydrocarbons – contains only hydrogen and carbon atoms • Straight line chains of carbon atoms • Alicyclic hydrocarbons have carbon atoms forming a closed ring. Still considered aliphatic

19. Naming Organic Compounds • In organic chemistry, names have a root and a suffix. • The root describes the number of carbons present in the chain or ring. • The suffix describes the type of compound it is.

20. Naming Organic Compounds

21. Naming ALKANES • Find the parent chain (the longest continuous chain of carbon atoms). Use the appropriate root and the suffix-ane.

22. Naming ALKANES • Find the parent chain. Use the appropriate root and suffix. • Number the carbon atoms, starting from the end closest to the branch(es) so that the numbers are the lowest possible • Identify any branches and their location number on the parent chain (us the suffix –yl for branches) • Write the complete IUPAC name, following the format: (number of location, if necessary) – (branch name) (parent chain) 2-methylheptane

23. Naming ALKANES • If more than one of the same branch exist, use a multiplier to show this (di, tri). Remember to include all numbers • Draw 2,4,6-trimethylheptane

24. Naming ALKANES • If different branches exist, name them in alphabetical order ethyl before methyl (e before m in the alphabet)

25. Naming ALKANES • If there is more than one branch of the same type, a locating number is given to each branch and a prefix indicating the number of that type of branch is attached to the name. • This numbering prefix does not affect the alphabetical order of the branches • Draw the structural formula for 3,4-dimethylhexane

26. Summary of Naming Alkanes • Find the parent chain. Use the appropriate root and suffix. • Number the parent chain carbon atoms, starting from the end closest to the branch(es) so that the numbers are the lowest possible • Identify any branches and their location number on the parent chain (us the suffix –yl for branches) • If more than one of the same branch exist, use a multiplier (di, tri) to show this. Remember to include all numbers • If different branches exist, name them in alphabetical order • Separate numbers from numbers using commas, and numbers from words using dashes (no extra spaces)

27. Don’t forget • Questions will specifically ask about structural, condensed structural or line structural formulas. • You must be comfortable drawing any of the three

28. Practice • Write the IUPAC name for the following 2,5-dimethyl-4-propyloctane

29. Correct the following names: • 4-ethyl-2-methylpentane • ACTUALLY 2,4-dimethylhexane • ALWAYS LOOK FOR LONGEST CHAIN!!

30. Correct the following name: • 4,5-dimethylhexane • Actually 2,3-dimethylhexane • **Want branch numbers to be as low as possible

31. CYCLOALKANES • Based on evidence, chemists believe that organic carbon compounds sometimes take the form of cyclic hydrocarbons: • Cycloalkanes: Alkanes that form a closed ring • General Formula CnH2n • Two less hydrogens are present than in straight chain alkanes because the two ends of the molecule are joined • Are these considered saturated?? Yes, because they have only single bonds and the max amount of hydrogen's bonded to the carbons • Cyclo-compounds will have a higher boiling point than their straight chain partners (because there is an additional bond present)

32. Naming CYCLOALKANES • Cycloalkanes are named by placing the prefix cyclo in front of the alkane name, as in cyclopropane and cyclobutane • If branches are present, treat the cycloalkane as the parent chain and identify the branches. • Since there is no end at which to start the numbering, use the lowest numbers possible

33. Name the following: 1. 2. 1,2-dimethylcyclopentane ethylcyclohexane **Why don’t we need a number?

34. Today’s homework • HW Book page 1 – check over as a class • Pg. 370 #7 (a-c) ,9(a-c), 10 (a-b) 11 (a-c) • Pg. 372 #5-6 (Extra) • What is coming up tomorrow? • Naming Alkenes, Alkynes, Cycloalkenes and Cycloalkynes • Comparing properties of Isomers

35. Naming Organic Compounds: Alkenes and Alkynes • Today’s Objectives: • Name and draw structural, condensed structural, and line diagrams and formulas for saturated and unsaturated aliphatic (including cyclic • Containing up to 10 carbon atoms in the parent chain/cyclic structure • Containing only one type of a functional group or multiple bond • Using the IUPAC nomenclature guidelines • Identify types of compounds from the functional groups, given the structural formula • Define structural isomerism and relate to variations in properties Section 9.3 (pg. 374-380)

36. Review: • Find and name all of the isomers of pentane (C5H12(l))

37. Structural Isomerism • Compound with the same molecular formula but different structures • They will have different chemical and physical properties – based on their different structures

38. Alkenes and Alkynes • Alkenes – hydrocarbons containing a double C-C bond • General formula (CnH2n) - (like cycloalkanes) • Alkynes – hydrocarbons containing a triple C-C bond • General formula (CnH2n-2) – (like cycloalkenes) • Alkenes and Alkynes are considered unsaturated compounds. They do not have the maximum number of hydrogen atoms surrounding each carbon. • Reactivity: Alkynes (highest), Alkenes, Alkanes (lowest)

39. Naming Alkenes and Alkynes • Find the parent chain. It MUST contain the multiple bond. • If the bond is a double, the suffix for the parent chain will be -ene • If the bond is a triple, the suffix for the parent chain will be –yne • Count carbon atoms so that the multiple bond will be on the lowest possible number. Indicate the number that the multiple bond falls on directly before the suffix • Name branches as before

40. Naming Alkenes and Alkynes • Draw the following as condensed structural formulas: 4-methylpent-2-yne methylpropene (why don’t we need a number?)

41. Naming Alkenes and Alkynes • Name the following: 3-methylbut-1-ene 5-methylhex-2-ene

42. Naming Alkenes and Alkynes • It is possible for a molecule to have more than one double bond. These are called alkadienes and have the same general formula as alkynes (CnH2n-2) • If this is the case, indicate both numbers where the double bond is formed, and change the suffix to –diene. a) Draw buta-1,3-diene: b) What is the IUPAC name for the following: buta-1,2-diene

43. Cycloalkenes and -ynes • The rules for naming cycloalkenes and cycloalkynes are the same as naming cycloalkanes • The numbering for the carbon atoms begins with the double bond; the carbons of the double bond are carbons 1 and 2; lowest numbers possible • Draw 3-methylcyclohexene as a condensed structural formula

44. Today’s homework • HW Book page 2 – go through as a class • Pg. 377 #1-5 • Pg. 380 #6 (a-b) , 7 (a-b), 11 (a-b) • Due tomorrow /22 marks • What is coming up tomorrow? • Hydrocarbon Quiz #1 (MON) • Naming Aromatics • Boiling point and Chemical Properties Analysis

45. Naming Organic Compounds: Aromatics • Today’s Objectives: • Name and draw structural, condensed structural, and line diagrams and formulas for aromatic carbon compounds • Using the IUPAC nomenclature guidelines • Identify types of compounds from the functional groups, given the structural formula • Define structural isomerism and relate to variations in properties Section 9.4 (pg. 381-385)

46. Hydrocarbon Quiz #1

47. Aromatics • Originally, organic compounds with an aroma or odour were called aromatic compounds • Now, aromatics refer to compounds containing a benzene-ring structure • Benzene’s formula is C6H6, which would suggest a highly unsaturated and reactive compound • Benzene is actually quite unreactive and is considered more stable than alkenes and alkynes • Did You Know?? Benzene is a carcinogen and is found naturally in petroleum – why would this be a problem?

48. We will use this line structural formula to represent benzene in compounds The three double bonds resonate resulting in an overall bond length somewhere in between a single and a double bond, explaining benzene’s stability • What do we know about benzene? • Formula is C6H6 (3D link) • Unreactive – so no true double or triple bonds • Carbon-carbon bonds are the same length and strength • Each carbon is bonded to a hydrogen • So what does benzene look like??

49. Common Aromatic Compounds • Include Aspirin and Vanillin (one of the flavour molecules in vanilla) • You will notice many aromatic molecules are often depicted using a condensed structural formula except for the benzene ring, which is shown as a line structural formula. • This combination is commonly used by chemists, and we will use this method when drawing aromatics.

50. Naming Aromatics • If an alkyl branch is attached to a benzene ring, the compound is named as an alkylbenzene. • Alternatively, the benzene ring may be considered as a branch of a large molecule: in this case, the benzene ring is called a phenyl branch. Which has a phenyl branch? An alkylbenzene Contains a phenyl branch