1. orgchem.chem.uconn.edu Organic Chemistry Today Overview Characteristics of organic compounds Hydrocarbons Fully saturated hydrocarbons Alkanes Chemical structure, condensed structure and formulas

2. Objectives: www.brainscape.com In this unit: What these compounds look like What their names mean How they take part in the reactions that fuel our lives ORGANIC CHEMISTRY

3. orgchem.chem.uconn.edu Carbon is the element of Life www.e-reful.com There was a time when we thought that carbon compounds could only be produced by living things ORGANIC COMPOUNDS Early 1800’s: Mysticism Friedrich Wohler Synthesized urea which proved that chemical molecules could be created and manipulated ORGANIC CHEMISTRY What is it about carbon that makes it so special? Involves the study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.

4. orgchem.chem.uconn.edu Organic Compounds  Contain carbon  Have covalent bonds  Have low melting points  Have low boiling points  Burn in air (oxygen)  Are soluble in nonpolar solvents  Form large molecules www.carolinaskiffowner.com

5. orgchem.chem.uconn.edu Carbon Carbon is the foundation of most biological molecules Group 14 on the periodic table Like all other compounds in this group – 4 valence electrons. Bond to four other atoms Make possible a variety of compounds. sciencenotes.org

6. orgchem.chem.uconn.edu HYDROCARBONS Most simple organic compounds containing only one carbon and hydrogen For classification purposes, all other organic compounds are considered derivatives of hydrocarbons. Hydrocarbons can be divided into aromatic and aliphatic hydrocarbons. SATURATED PURE HYDROCARBONS Organic compounds containing only carbon and hydrogen AND only single bonds. auto.howstuffworks.com en.wikipedia.organimals.howstuffworks.com

7. orgchem.chem.uconn.edu Hydrocarbons Aliphatic Aromatic Alkanescycloalkanes AlkenesAlkynes

8. orgchem.chem.uconn.edu Aromatic hydrocarbons contain one or more benzene ring. Benzene (C 6 H 6 ) is the most important aromatic hydrocarbon. It is a clear, colorless liquid with a distinct odor, and is a carcinogen (cancer-causing agent.) Aromatic Hydrocarbons

9. orgchem.chem.uconn.edu Aliphatic Hydrocarbons Aliphatic hydrocarbons: hydrocarbons having no benzene rings. Four types Alkanes Cycloalkanes Alkenes Alkynes

10. orgchem.chem.uconn.edu Alkanes: Saturated hydrocarbons Fully saturated hydrocarbons Simple hydrocarbons that contain C and H only Contain single bonds C-C Can be arranged in a chain or a ring Have 4 bonds to every carbon (C) atom Are nonpolar

11. orgchem.chem.uconn.edu Alkanes: properties and naming Properties Contain C and H only Contain single bonds C-C Have 4 bonds to every carbon (C) atom Are nonpolar Straight Chain alkanes Structural formulas differ from the next by an increments of -H 2 -

12. orgchem.chem.uconn.edu Straight Chain alkanes Methane: CH 4 Main compound in natural gas Ethane: two carbons side-side Production of plastics chemsocialpolicy.wikispaces.com www.dayasriolk.top CH 3

13. orgchem.chem.uconn.edu Straight Chain alkanes commons.wikimedia.org Propane: C 3 H 8 cooking, heating, vehicles, etc. Butane: commons.wikimedia.org

14. orgchem.chem.uconn.edu Straight Chain alkanes Pentane: Hexane: C 5 H 12 www.answers.com myorganicchemistry.wikispaces.com

15. orgchem.chem.uconn.edu Name # carbons Structural Formula Heptane 7 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Octane 8 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Nonane 9 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Decane 10 CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 Straight Chain alkanes

16. A. What is the condensed formula for B. What is its molecular formula? C. What is its name? Timberlake LecturePLUS 16 Straight Chain alkanes CH 3 CH 2 CH 2 CH 3 C 4 H 10 butane

17. orgchem.chem.uconn.edu Organic Chemistry General Chemistry Quick review Alkane reactions Isomers Chemistry in the Community Graphing Alkanes

18. orgchem.chem.uconn.edu Cycloalkanes Cycloalkane have rings of carbon atoms. Each carbon atom is fully saturated. The smallest possible ring: C 3 H 6. Naming cycloalkanes: cyclo____________ Molecular structureCondensed structural formula Cyclo_______________ Name Note: there is a carbon atom at each corner and enough hydrogens are assumed to be attached for the carbon atom to be fully saturated

19. orgchem.chem.uconn.edu Cycloalkanes Fill in the boxes: Structural formula Condensed Structural Formula Name

20. orgchem.chem.uconn.edu Note that in the condensed structural formulas, there is a carbon atom at each corner and enough hydrogens are assumed to be attached to give a total of four single bonds. Cycloalkanes

21. orgchem.chem.uconn.edu Graphing Alkanes: 1.Estimate the average change in boiling point (°C) when one carbon atom and two hydrogen atoms are added to a particular chain. 2.Estimate the boiling point of undecane (C 11 H 24 ) 3.Estimate the boiling point of dodecane (C 12 H 26 ) 4.Estimate the boiling point of tridecane (c13H28) 5.For the alkanes we have studied thus far, what is the relationship between the strength of the intermolecular forces between the molecules, and the number of carbon atoms in each molecule Finish the table two ( from work sheet and answer questions

22. orgchem.chem.uconn.edu Quick Review: 1.What is organic chemistry? 2.How many valence electrons does carbon have? 3.Carbons bond to ________ other atoms. 4.What is a hydrocarbon? 5.What is a alkane?

23. orgchem.chem.uconn.edu chempaths.chemeddl.org http://www.peoi.org/Courses/Coursesen/chemintro/ch/ch16b.html Name this alkane What is the condensed structure? What is the formula? Name this alkane What is the condensed structure? What is the formula? Name this alkane What is the condensed structure? What is the formula? Review

24. orgchem.chem.uconn.edu Alkane Reactions 1.Combustion: burning Requires a hydrocarbon, oxygen and a source of heat energy / catalyst 2.Halogenation Replacement of hydrogen atoms with halogens www.eoearth.org 3.Dehydrogenation Removal of water molecules Carbon atoms are no longer saturated with hydrogen atoms

25. orgchem.chem.uconn.edu Alkenes hydrocarbons (compounds containing only C and H) that have one or more C=C double bonds (two C atoms are linked by 4 shared electrons). One or more double bonds Hydrocarbons that are related to fats / lipids Saturated Unsaturated Monounsaturated Omega-3 Hydrogenated Transfatty acids alevelnotes.com

26. orgchem.chem.uconn.edu Alkynes Unsaturated hydrocarbons (compounds containing only C and H) that have one or more triple bonds (two C atoms are joined by 6 shared electrons). Few alkynes are known to occur naturally because they are very reactive Can be synthesized from other organic compounds chemistrywithelevens.blogspot.com

27. orgchem.chem.uconn.edu Organic Chemistry Today Alkyl groups Isomers Functional groups

28. orgchem.chem.uconn.edu Alkyl Group Alkyl group contains one less hydrogen than the corresponding alkane. In naming this group the “-ane” is dropped and “-yl” is added. For example, methane becomes methyl. Ethane becomes ethyl.

29. orgchem.chem.uconn.edu Alkyl Group Always count left to right and count the longest chain Parent chain: longest string of carbon atoms in a molecule

30. orgchem.chem.uconn.edu Isomers Molecules that have the same molecular formula but different structures Contain different properties such as boiling and melting points and chemical reactivity. In the case of alkanes – there is more than one way to arrange atoms Example: butane and isobutene – both have a molecular formula of C 4 H 10, but their structural formula and arrangement is different. www.britannica.com

31. orgchem.chem.uconn.edu possible to construct a different structural arrangement: -Using the same number and types of atoms -Without violating the octet rule Same atoms may be connected to one another in different, but valid, ways. Isomers Copyright © Houghton Mifflin Company. All rights reserved

32. orgchem.chem.uconn.edu Cis and Trans structures 1 Methyl grp 2 3 4 2012books.lardbucket.org

33. orgchem.chem.uconn.edu

34. FUNCTIONAL GROUPS specific groups of atoms or bonds within molecules that are responsible for the characteristic chemical reactions. Derivative of hydrocarbons Organic molecule characteristics Depends on the number, arrangement and type of atoms

35. orgchem.chem.uconn.edu Review canadaconnects.caen.wikibooks.org

36. orgchem.chem.uconn.edu Amine Compounds that contain nitrogen joined to at least one alkyl group NH 2 group Derivatives of ammonia amino acids (proteins) have amine groups attached Many amines have medicinal applications. Copyright © Houghton Mifflin Company. All rights reserved

37. orgchem.chem.uconn.edu Alcohol OH C Alcohols are organic compounds containing the hydroxyl group, —OH, attached to an alkyl group. The most simple alcohol is methanol Other examples: Ethanol: alcoholic beverages, perfumes, dyes and tarnishes Rubbing alcohol is another alcohol: 2-hydroxypropane or isopropyl alcohol Ethylene glycol is an alcohol used widely as an antifreeze and coolant. Copyright © Houghton Mifflin Company. All rights reserved

38. orgchem.chem.uconn.edu Carboxylic acid Carboxylic acids contain the carboxyl group. (–COOH) www.chemistry-drills.com Copyright © Houghton Mifflin Company. All rights reserved Examples: Formic acid Vinegar: acetic acid

39. orgchem.chem.uconn.edu Esters Ester – a compound that has the following general formula RCOOR’ most esters have pleasant odors. C = O (differentiates between esters and ethers) Fragrances and tastes of flowers and fruits www.cram.com

40. orgchem.chem.uconn.edu Amides Amides are nitrogen-containing organic compounds Amide formation is similar to ester formation but there is a double with Oxygen and a NH 2 group attached to the same carbon atom. en.wikibooks.org C

41. orgchem.chem.uconn.edu Ether Organic compounds that contain an ether group. Charaterisized by an oxygen sandwiched between two carbons. example is the solvent and anesthetic diethyl ether,.solventanestheticdiethyl ether www.studyblue.com

42. orgchem.chem.uconn.edu Ketones and aldehydes 2012books.lardbucket.org simple compounds that contain a carbonyl group (a carbon-oxygen double bondcarbonyl group Do not have reactive groups Many ketones are known and many are of great importance in industry and in biology. Examples include many sugars (ketoses) and the industrial solvent acetone, which is the smallestsugarsketosessolventacetone ketone www.proprofs.com

43. orgchem.chem.uconn.edu Polymers M olecules with high molar masses and are composed of a large number of repeating units. Naturally occurring polymers: proteins, starches, cellulose, and latex. Synthetic polymers are produced commercially and have a wide range of properties and uses. Plastics First synthetic polymer was prepared by Leo Baekeland in 1907.

44. orgchem.chem.uconn.edu Polymer Lab 1.Working in groups of 2 or 3 (no more) 2.Pre-Lab 3.Prepare Sample mixture 4.DO NOT THROW ANY SOLUTION DOWN THE SINK DRAINS. USE TRASH CANS! 5.Define terms and concepts 6.Write out your observations in the table provided 7.Answer questions

45. orgchem.chem.uconn.edu Additional References: Crash Course: https://www.youtube.com/watch?v=UloIw7dhnlQhttps://www.youtube.com/watch?v=UloIw7dhnlQ Khan Academy: https://www.khanacademy.org/science/organic-chemistry/gen-chem-review/dot-strcutures-jay/v/dot- structures-i-single-bonds-1https://www.khanacademy.org/science/organic-chemistry/gen-chem-review/dot-strcutures-jay/v/dot- structures-i-single-bonds-1 Organic Chemistry Tutor Phillips, John S., Strozak, Victor S., Wistrom, Cheryl, 2005 Chemistry: Concepts and Applications, Glencoe / McGraw-Hill, Columbus, Ohio. Wikipedia: https://en.wikipedia.org/wiki/Organic_chemistryhttps://en.wikipedia.org/wiki/Organic_chemistry http://scifun.chem.wisc.edu/chemweek/polymers/polymers.html