Chemistry 1B CHEM1102

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1 Chemistry 1B CEM1102 Lecture 1 Welcome & Introduction to rganic Chemistry Chris McErlean, Room 518a, C.McErlean@chem.usyd.edu.au

Faculty of Science Code for Success The First Year

information and resources to ease your transition and

The site can be accessed via sydney.edu.

Management System (icon link can be found on the right)

2 Faculty of Science Code for Success The First Year Science ecommunity is a website that provides information and resources to ease your transition and maximise your success as a scientist at Sydney. The site can be accessed via sydney.edu.au/current_students, by logging into the Learning Management System (icon link can be found on the right) then clicking the ecommunities tab in the bar menu. My Degree Research and Information Skills FAQs

3 Welcome to First Year Chemistry Questions or problems with the course? Director of First Year Studies Adam Bridgeman (Room 543a) Adam Questions or problems with the labs? Director of First Year Laboratories Ron Clarke (Room 318) Ron

Not sure about something ask Sophie! First Year Enquiry ffice (10 am - 3.15 pm) firstyear@chem.usyd.edu.au Sophie Need extra help with course work?

4 Not sure about something ask Sophie! First Year Enquiry ffice (10 am pm) firstyear@chem.usyd.edu.au Sophie Need extra help with course work? First Year Chemistry Learning Centre At the back of Lab D textbooks, computers etc and. Tutors available Mon-Thu, 1-2pm from week 2 for free consultations CEM1102 Discussion Board on elearning Submit your questions and a tutor will reply

5 Information and Resources First Year Chemistry web site: firstyear.chem.usyd.edu.au CEM1102 website: firstyear.chem.usyd.edu.au/chem1102 Access answers to tutorial problems, lecture notes, exam papers etc elearning : elearning.sydney.edu.au/ Access pre-lab quizzes and resources from off-site CEM1102 Discussion Board ChemCAL: chemcal.chem.usyd.edu.au Self-help tutorials and quizzes

6 Syllabus and Learning utcomes firstyear.chem.usyd.edu.au/chem1102/syllabus.shtml firstyear.chem.usyd.edu.au/chem1102/learningoutcomes.shtml Lecture Notes firstyear.chem.usyd.edu.au/chem1102/lecture_notes.shtml Username chem1102 Password carbon12 Textbook Recommended (single book covers both semesters): Blackman, Bottle, Schmid, Mocerino and Wille, Chemistry and SI Chemical Data (package), 2012 (John Willey) ISBN:

7 Tutorials Start in week 1 Check answers to questions in the problem book on the web before tutorial Laboratory Work Starts in week 2 check your timetable If you ve previously passed this lab course, see Enquiry ffice about exemption Assessment 15% laboratory assessment (see first lab session for details) 15% tutorial quizzes (3 per semester: weeks 5, 9 and 12) 10% research assignment on spectroscopy (from week 4 7) 60% 3 hour exam at the end of semester

8 Laboratory andbook Free collect during your first lab session in week 2 Safety glasses must be worn btainable when you get your laboratory book in week 2 or from the Union Laboratory Coat - Complying to Australian Safety Standards btainable from the Co-p bookshop, Wentworth Newsagency or Faculty estore ( for less than $30 Must be white and long sleeved Footwear and Long air Covered footwear must be worn during all lab classes no sandals or thongs Long hair must be tied back

9 Lecturers We are very approachable - if you have questions, talk to us! There are 3 series of this unit: Weeks 1-7: Dr Matt Todd (1) (matthew.todd@sydney.edu.au) A/Prof Richard Payne (2) (richard.payne@sydney.edu.au) Dr Chris McErlean (3) (christopher.mcerlean@sydney.edu.au) Weeks 8-13: A/Prof Tony Masters (1 and 3) (anthony.masters@sydney.edu.au) Dr Siggi Schmid (2) (siegbert.schmid@sydney.edu.au)

10 check your university regularly

11 CEM1102 verview Main topics rganic chemistry (Weeks 1-7) Molecular Structure and Stereochemistry rganic Synthesis Structure Determination Inorganic & Physical Chemistry (Weeks 8-13) Acids and Bases States of matter Coordination chemistry

12 CEM1102 Textbooks Recommended texts: Chemistry Blackman, Bottle, Schmid, Mocerino, Wille others are Chemistry: Molecular Nature of Matter & Change Martin Silberberg, McGraw ill, 3rd Edition rganic Chemistry John McMurry, Brooks Cole, 6th Edition (or 5th ed) Fundamentals of rganic Chemistry John McMurry, 5th Edition; Brooks Cole

13 CEM1102 Study Formal: Lectures Tutorials Informal: Study groups Duty tutor Discussion boards n-line: USYD elearnig ChemCAL Self-help problems ff-line: Assignments Textbooks Lecture notes Plan your study time from the start now!

14 CEM1102 rganic Chemistry 1. Representations of Molecular Structure 2. Alkanes, Alkenes, Alkynes 3. Aromatic Compounds 4. Structure Determination 5. Alcohols & Amines 6. Stereochemistry 7. rganic alogen Compounds 8. Aldehydes & Ketones 9. Carboxylic Acids & Derivatives 10.Synthetic Strategies 3 C Aspirin

15 CEM1102 Timeline Week 1 Drawing Structures; Alkanes; Isomerism Week 2 rganic Reactions; Alkenes; Substitution Reactions Week 3 Structural Determination: Spectroscopy! Week 4 Alcohols; Amines; Stereochemistry Week 5 More on Stereochemistry; Aldehydes & Ketones Week 6 Carboxylic Acids; Esters & Amides; Synthetic Polymers Week 7 Biopolymers; Synthetic Strategies; Review

16 rganic Chemistry 1. Representations of Molecular Structure 2. Alkanes, Alkenes, Alkynes 3. Aromatic Compounds 4. Structure Determination 5. Alcohols & Amines 6. Stereochemistry 7. rganic alogen Compounds 8. Aldehydes & Ketones 9. Carboxylic Acids & Derivatives 10.Synthetic Strategies 3 C Aspirin

17 What is rganic Chemistry? Chemistry of Life (proteins, sugars, nucleic acids ) Based around the chemistry of carbon organic molecules possess carbon-carbon bonds a few other elements (mainly ) Concerns transformations (reactivity) and building (synthesis) of organic structures Serine 2 N C 2 C 3 7 N 3 C, 34%;, 7%; N, 13%;, 46%

18 What is rganic Chemistry? Carbon has unique properties Atomic Number 6 1s 2 2s 2 2p 2 Valence of 4 Mid-range electronegativity C-C and C- bonds are strong and unreactive provides solid scaffolds C can bond to itself to metals to heteroatoms Geometrically flexible cabable of catenation forms chains, rings, multiple bonds.

19 What is rganic Chemistry? 2 C CCl 3 Chloroform N 2 N Nutrasweet C 2 Me Ph Properties depend on structure uge number of organic compounds known (even more yet to be discovered) To communicate unambiguously, need to master Representation & Nomenclature Ac Bz ie N how to draw molecules Ph Ac N CF 3 Taxol Aspirin Prozac

20 C 2 6 C 3 C 2 C C C C Ethanol C 2 5 C 2 6 ow to Draw rganic Compounds? Line structure

21 General Drawing Concepts 1. Lines represent bonds 2. C is basis of structure (chains and rings of carbon atoms) carbon atoms assumed to be at intersections and ends of lines C bonds omitted (hydrogen count assumed from valence) All heteroatoms shown (+ s bound to heteroatoms) 3. Valence 4 for C 3 for N 2 for 1 for, Cl, Br, I 4. Geometry depends on hybridisation Indicate bond angles (~120 or 180 )

22 Pop Quiz Draw a line representation for 1. C 3 CC 2 C 2 C 3 2. (C 3 ) 3 CCBrC 2 C 2 3. C 3 CClC=C 2 4. C 6 6 Can you name any of the above compounds?

23 Pop Quiz Draw a condensed formula for C N Can you name the above compounds?

24 Showing Bonds in 3D When you need to show the 3D shape of a molecule Bonds in the plane of the paper: C Bonds coming towards you: C Bonds going away from you: C For example C 4 : C

25 Summary You should now be able to 1. Understand the basis of drawing organic structures 2. Convert between a condensed molecular formula and a skeletal or line structure 3. Determine the formula of a molecule from its skeletal representation Next Lecture Bonding and Nomenclature

Appendix 2: ther Ways to Draw Space-Filling Representation: Ethanol C 2 5 C 2 6 C 2 6 Advantages: Disadvantages: Gives an indication of the extent of the molecule

26 Appendix 2: ther Ways to Draw Space-Filling Representation: Ethanol C 2 5 C 2 6 C 2 6 Advantages: Disadvantages: Gives an indication of the extent of the molecule Indicates perspective (3-D image) Difficult to draw by hand requires computer Not obvious what elements are present Bond angles hidden Difficult to use for mechanisms

27 General Drawing Concepts 1. Lines represent bonds 1, 2 or 3 lines for single, double, triple bonds 2. C is basis of structure (chains and rings of carbon atoms) carbon atoms not shown assumed to be at intersections and ends of lines C bonds omitted (hydrogen count assumed from valence) All heteroatoms shown (+ s bound to heteroatoms) 3. Valence 4 for C 3 for N 2 for 1 for, Cl, Br, I 4. Geometry depends on hybridisation Indicate bond angles (~120 or 180 ) 5. In condensed formulae, atoms bonded to a C atom are listed after it

28 Appendix 2: ther Ways to Draw Line Representation: Ethanol C 2 5 C 2 6 Advantages: Disadvantages: Quick to draw Bond angles and heteroatoms represented Determining molecular formula takes time for beginners C 2 6

29 Appendix 2: ther Ways to Draw Traditional Representation: Ethanol C 2 5 C 2 6 C C C 2 6 Advantages: All atoms and bonds drawn All molecules represented as 2-D images Disadvantages: Bond angles are not 90 0 Tedious to draw

30 Appendix 2: ther Ways to Draw Condensed Molecular Formula: Ethanol C 2 5 C 2 6 C 3 C 2 Advantages: Disadvantages: C 2 6 Indicates connectivity Easily written Enables naming of the constitutional isomer Does not represent stereochemistry where applicable No indication of molecular shape Again slightly tedious

31 Appendix 2: ther Ways to Draw Structural Formula: Ethanol C 2 5 C 2 6 Advantages: Disadvantages: Wedge and hash bonds indicate 3-D structure Atoms and bond angles represented Enables accurate naming of the molecule Permits advanced mechanistic understanding Takes time to draw C 2 6 C C

32 Appendix 2: ther Ways to Draw Ball & Stick Representation: Ethanol C 2 5 C 2 6 Advantages: Disadvantages: Bond angles represented Some indication of space occupied Stereochemistry indicated where applicable Type of atom not specified Requires computer/models C 2 6

33 Pop Quiz Draw a line representation for C 3 CC 2 C 2 C 3 Draw a condensed formula for Can you name either of the above compounds?

University of Sydney Chemistry 1B (CHEM1102) Organic Chemistry Lecture Notes

University of Sydney Chemistry 1B (CHEM1102) Organic Chemistry Lecture Notes University of Sydney hemistry 1B (EM1102) rganic hemistry Lecture Notes Topic 1 Introduction & isomers 2 Topic 2 Alkenes, alkynes, arenes 20 Topic 3 Structure determination 27 Topic 4 Alcohols and amines