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Organic Chemistry The study of Carbon and its compounds.

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1 Organic Chemistry The study of Carbon and its compounds

2 ORGANIC CHEMISTRY The study of compounds containing Carbon atoms. Carbon has 4 valence electrons, always draw it with 4 covalent bonds around it. When it forms all single bonds the shape of around the carbon is TETRAHEDRAL.

3 Properties Solubility – Most nonpolar (like dissolves like) – Most compounds are insoluble in water – Soluble in non-polar solvents H O O

4 Properties Most are non-electrolytes – Covalent, no conductivity – (an exception is organic acids)

5 Properties Low Melting/ Boiling Points

6 Properties Rate of Reaction – Slower than inorganic compounds – High activation energy

7 Properties Bonding – Nonpolar covalent – Carbon has 4 valance electrons- tetrahedron – Carbon can bond with itself indefinitely (in dif. shapes, many variations) Always make 4 bonds C

8 HYDROCARBONS Compounds containing only C and H. 3 open chain families ALKANES ALKENES ALKYNES

9 Homologous Series or families Group of related compounds in which each member differs from the next by one carbon and 2 hydrogens

10 Alkanes Single-bonded hydrocarbons Hydrocarbon= only carbon and hydrogen atoms IUPAC nameMolecular FormulaGeneric Formula methaneCH 4 ethaneC 2 H 6 propaneC 3 H 8 butaneC 4 H 10 pentaneC 5 H 12 hexaneC 6 H 14 C n H 2n+2 heptaneC 7 H 16 octaneC 8 H 18 nonaneC 9 H 20 decaneC 10 H 22 As the molecular size and dispersion forces increase, the boiling point and freezing point increase

11 Table Q

12

13 Alkenes have one Double-bonded hydrocarbon Unsaturated Same prefix as alkanes, with suffix -ene Dienes contain TWO double bonds, and are not alkenes!

14 Alkynes one Triple-bonded hydrocarbon Unsaturated Same prefix as alkanes, and alkenes, with suffix - yne

15 Saturated vs Unsaturated compounds Single BondsDouble/Triple Bonds

16 Benzene 6 carbon atoms in a ring Aromatic Hydrocarbon Only structure really needs to be known for the regents. Cyclic Hydrocarbons

17 How to draw and name different organic compounds? ISOMERS

18 Isomers Compounds with: the same molecular formulas different structural formulas C 4 H 10 Normal Butane2-Methyl Propane Although these structures look different, they both have the same molecular formula of C 4 H 10

19 ISOMERS Same molecular formula but different structural formula. Have different chemical and physical properties.

20 Alkyl Groups Have 1 less hydrogen (H) than the corresponding alkane Ex: Methyl CH 3 – 1 less H than CH 4 Ethyl C 2 H 5 – 1 less H than C 2 H 6

21 Rules for naming organic compounds For Straight or continuous chains: normal form n-alkanes. For branched compounds: 1.Find the longest continuous chain and name the compound. Branches are alkyl groups and end with –yl. 2. The location of the alkyl group is determined by assigning numbers to the carbon atoms of the longest chain, beginning at the end that will give the lowest number to the carbon that contains the alkyl or special group.

22 Drawing Rules Step 1Step 2 -ane, Alkane: draw all single bonds -ene, Alkene: draw all single bonds except draw a double on the number carbon that is present in the name -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that is present in the name Step 3 It’s as easy as 1, 2, 3…. Make sure all carbons have 4 bonds

23 Draw Hexane 1 st Task: CCCCCC Condensed Formula: CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3

24 Draw 1-Pentene 2 nd Task: -ane, Alkane: draw all single bonds -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows

25 Draw 2-butyne 3 rd Task: -ane, Alkane: draw all single bonds -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows

26 Draw: 2, 3-dimethylbutane

27 Practice Problems Using Table Q, what type of homologous structure is this and why? Why? General formula Structure Name Why? General formula Structure Name

28 Objective : Functional groups. How to distinguish them and what do they do to an organic compound? Table R

29 Organic compounds and their functional groups

30

31 Halides (Halocarbons) A halide is formed when one or more halogen elements attach themselves to a chain of carbons atoms Halogen include all the elements in group 17

32 Naming Halocarbons Halocarbons are usually formed from Alkenes – This is because the double bonds that are present break; leaving empty bonds on the carbons where the halogens are now able to form Double Bond

33 Naming Halocarbons Every halogen has its own prefix to put at the beginning of its name – It is listed in Table R When the bonds brake;the halogens fill the empty space

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35 Alcohols Contain 1 less Hydrogen and in its place there is an –OH group instead. Even though alcohols have an –OH group, they are not a considered a base. – This is because there are covalent bonds holding the –OH to the carbons and bases don’t have covalent bonds present on the –OH. – When in solution, acids only release and H+ and bases release OH-

36 Naming Alcohols You start with Alkane. (In this case, Methane) Take away one of the Hydrogen atoms. Add an –OH group to the empty space For the name; drop the –e at the end of the prefix (Methane) and add –ol to name the Alcohol!

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38 Ether In an ether, there is always an oxygen atom in between two carbons. And there can be any number of carbons on each side of the oxygen.

39 Naming Ethers Count the amount of carbons on the left side of the Oxygen first. Count the number of carbons on the right side of the oxygen. The carbons on the left make Methyl and the carbons on the right make Ethyl, then put Ether at the end.

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41 Aldehyde Aldehydes are known when there is one double bonded oxygen atom at the beginning or the end of a carbon chain.

42 Forming Aldehydes Start with a carbon chain (butane). Drop off two Hydrogen atoms. Add a double bonded oxygen to the open carbon.

43 Name It! Four Carbons = butane Since all aldehydes end in –al. Drop the –e and add –al to the end.

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45 Ketone Ketones can be identified by the oxygen double bonded to a carbon in the middle of a carbon chain.

46 Name a Ketone We have a chain of carbons (4=butane) If the double bonded oxygen is found in the middle of a carbon chain then it is a ketone and the –e must be dropped and add –one in its place

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48 Organic Acids!!!!!! Contains a double bonded oxygen and an –OH to the last carbon in the chain Called acids because H+ ions are released when dissolved in water Since ions are present when dissolved, an electric current can be conducted through the water Organic acids are electrolytes!

49 Name the acid Hexane Drop off the three hydrogen atoms at the end of the chain Add a double bonded oxygen atom and an –OH group to the open carbon atom REMOVE: -e ADD: -oic Acid AND THERE YOU HAVE IT!! Start with the carbon chain Form the Acid

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51 Ester Esters have two oxygen atoms present – One is connected by double bonds to a carbon atom – The other is connected by single bonds but to two carbon atoms An ester is formed from the reaction of an acid and an alcohol. And Esters smell goood!!

52 Title it! -count the number of carbons on the side that is only touching one carbon. -Add –yl as the suffix. -Now count the number of carbons in the chain attached to the two oxygen atoms. -All that’s left if to add –oate to the end

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54 Amine Amines contain a nitrogen atom – the nitrogen atom is found at the end of a carbon chain; attached to one carbon as well as two hydrogen.

55 Naming the Amine is easy There are only two steps involved! – Count the hydrocarbons – Drop the –e and add –amine

56

57 Amide Amides also contains a Nitrogen atom but attached to the same carbon is a double bonded oxygen.

58 How do I name it?? Amides are just the same as naming the amines except instead of adding –amine, you are adding –amide.

59 Amino Acids

60 Amino Acids… Contains both an amine and an organic acid Amine Organic Acid

61

62 NOTE: All the example on how the groups are named are shown on table R in the far right column. Note: The formulas on how each group is drawn is shown in the formula column.

63 OBJECTIVE: ORGANIC REACTIONS

64 Organic Reactions

65 1.Combustion TABLE I the first 6 rx are combustions Burning (reaction with oxygen) Hydrocarbons burn to form carbon dioxide and water Organic (hydrocarbon) + O 2 CO 2 +H 2 0 heat Test to show if there is Carbon Dioxide: Limewater (colorless) turns a milky white color with Carbon dioxide In a limited supply of oxygen, C and CO are formed

66 2. Substitution Replacement of one or more hydrogens in a saturated hydrocarbon by an halogen. Alkane + halogen(X 2 ) halocarbon + HX (g) + F 2 + HFF

67 3.Addition Adding one or more atoms at a double/ triple bond. Could be Hydrogenation (add H) Or Halogenation (add halogens) For alkenes and alkynes! + F 2 F HH

68 4.Esterification Acid and alcohol produce ester and water Fats are Esters dervied from glycerol (a trihydroxy alcohol- has 3 OH groups) and long fatty acids

69 Glycerol Fats are Esters derived from glycerol (a trihydroxy alcohol- has 3 OH groups) and long fatty acids

70 5.Saponification (hydrolysis) Ester breaks up into Acid and Alcohol (reverse of esterification) Produces soap Fat + Strong Base Soap + Glycerol

71 6.Fermentation C 6 H 12 O > 2 C 2 H 5 OH + 2 CO 2 Zymase (enzyme) Glucose Ethanol Carbon Dioxide

72 7 POLYMERIZATION Polymers are made of chains of smaller units called MONOMERS NATURAL POLYMERS Protein, starches, cellulose SYNTHETIC POLYMERS Nylon, rayon, polyethylene

73 7.Polymerization Small molecules join together to form bigger molecules (monomers to polymer) amino acid + amino acid + amino acid protein monomer + monomer + monomer polymer

74 Polymerization 2 Types: Condensation Polymerization: – Dehydration synthesis, occur when water is remove from primary alcohols. Have ether or ether linkages. – Make water and polymer Natural Protein (DNA) Starch cellulose Artificial Nylon Polyester silicone

75 Addition Polymerization – Monomers join together by breaking a double/triple bond nn number of ethene join together number of polyethylene

76 Finding missing reactants and products in Organic Reactions # of atoms on the left side of the arrow must equal # on the right After the elements/compounds are correctly written, change the coefficient Ex: C 2 H 6 + Cl 2 C 2 H 5 Cl + ______ HCl

77 Practice Regents Questions Go online to regentsprep.org! ns/questions.cfm?Course=CHEM&TopicCode= 06 ns/questions.cfm?Course=CHEM&TopicCode= 06

78 mes.html#top/draw.html#top mes.html#top/draw.html#top mes2.html#top mes2.html#top 11/unit-5-answers-handout.pdf 11/unit-5-answers-handout.pdf 11/hydrocarbon-nomenclature-handout.pdf 11/hydrocarbon-nomenclature-handout.pdf

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