2. VII. Organic

3. J Deutsch 2003 2 Organic compounds contain carbon atoms which bond to one another in chains, rings, and networks to form a variety of structures. Organic compounds can be named using the IUPAC system. (3.1ff)

4. J Deutsch 2003 3 Hydrocarbons are compounds that contain only carbon and hydrogen. Saturated hydrocarbons contain only single carbon-carbon bonds. Unsaturated hydrocarbons contain at least one multiple carbon-carbon bond. (3.1gg)

5. J Deutsch 2003 4 Homologous series of hydrocarbons:  Saturated hydrocarbons –Alkanes Only single bonds between carbons Name ends in ___ ane General formula C n H 2n+2 Methane CH 4 Ethane C 2 H 6  Unsaturated hydrocarbons –Contain at least one double or triple bond –Alkenes Contain one double bond Name ends in ___ene General formula C n H 2n –Alkynes Contain one triple bond Name ends in ___yne General formula C n H 2n-2

6. J Deutsch 2003 5 Table Q gives the general formula and examples (name and structure) of the homologous series of hydrocarbons.

7. J Deutsch 2003 6 Regents Question: 06/03 #24 Which element has atoms that can form single, double, and triple covalent bonds with other atoms of the same element? (1)hydrogen (2) oxygen (3) fluorine (4) carbon

8. J Deutsch 2003 7 Table P gives the prefix used to name the first 10 hydrocarbons in an homologous series.

9. J Deutsch 2003 8 The prefix of the name tells you how many carbons in the chain.The suffix tells you the type of hydrocarbon. Pentene C 5 H 10 Butene C 4 H 8 Propene C 3 H 6 Ethene C 2 H 4 Pentane C 5 H 12 Butane C 4 H 10 Propane C 3 H 8 Ethane C 2 H 6 Methane CH 4 Pent But Prop Eth Meth Prefix Pentyne C 5 H 8 5 Butyne C 4 H 6 4 Propyne C 3 H 4 3 Ethyne C 2 H 2 2 1 Number of Carbons Alkane C n H 2n+2 Alkene C n H 2n Alkyne C n H 2n-2 Example

10. J Deutsch 2003 9 Regents Question: 06/03 #21 Which hydrocarbon is saturated? (1) propene (2) ethyne (3) butene (4) heptane Alkanes are saturated hydrocarbons.

11. J Deutsch 2003 10 A structural formula show the way the atoms are arranged.  MethaneEthane HHH H C HHCCH HHH Each line represents a covalent bond - a shared pair of electrons.

12. J Deutsch 2003 11 A structural formulas show the way the atoms are arranged.  propene H H H C CCH H H  ethyne H CCH The double bonds makes this hydrocarbon an alkene The triple bonds makes this hydrocarbon an alkyne

13. J Deutsch 2003 12 Regents Question: 01/03 #13 The empirical formula of a compound is CH 2 Which molecular formula is correctly paired with a structural formula for this compound?

14. J Deutsch 2003 13 Chains of carbons can be branched  A carbon group connected to a chain is called an alkyl group.  To name the alkyl group, use the prefix for the number of carbons and add -yl. -CH 3 H H C H Methyl -C 2 H 5 H H H C C H H Ethyl

15. J Deutsch 2003 14 Carbon always has 4 bonds.  Hydrogen always has 1 bond  Oxygen always has 2 bonds  Nitrogen always has 3 bonds H O or O N C or C or C

16. J Deutsch 2003 15 Regents Question: 08/02 #42 Which structural formula is incorrect? Carbon always has four bonds.

17. J Deutsch 2003 16 Naming hydrocarbons with alkyl groups:  Find the longest continuous chain of carbons. This is the backbone. Find the name of the backbone.  Find the name of the alkyl group (or groups) attached to the backbone.  Name the alkyl group and then the name of the backbone.  Use a number to indicate which carbon the alkyl group is attached to if necessary.

18. J Deutsch 2003 17 4 H H C H H H H H H H C C C C C C H H H H H H H 4 3 256 Find the name of this hydrocarbon. Find the longest chain Find the alkyl group hexanemethyl 12 3 561 Counting from each direction find the carbon where the alkyl group is attached (the lower number) 3-

19. J Deutsch 2003 18 H H C H H H H H H C C C C C H H H H H H The longest chain does not have to be drawn straight. 3-methylhexane H H C H H H H H H C C C C C H H H H H H

20. J Deutsch 2003 19 Chains of carbons can form rings  Use a prefix cyclo when a ring is formed  To make a ring, two Hydrogen atoms are removed Cyclopentane is a 5 carbon ring with all single bonds.

21. J Deutsch 2003 20 Organic acids, alcohols, esters, aldehydes, ketones, ethers, halides, amines, amides, and amino acids are categories of organic molecules that differ in their structures. Functional groups impart distinctive physical and chemical properties to organic compounds. (3.1hh)

22. J Deutsch 2003 21 Functional Groups:  Functional groups are groups of atoms that have special chemical properties and which define the chemistry of an organic compound.  The following are common functional groups:

23. J Deutsch 2003 22 Reference Table R lists all the functional groups.

24. J Deutsch 2003 23 Reference Table R Cont’d.

25. J Deutsch 2003 24 Which pair below contains an alcohol and an acid? (1) a and b (3) b and d (2) a and c (4) c and d Regents Question: 06/03 #44 Given the formulas of four organic compounds:

26. J Deutsch 2003 25 Naming Halocarbons (-X)  Halocarbons (or halides) have a halogen (F, Cl, Br, I) in place of a hydrogen  Name the halogen first (fluoro, chloro, bromo, iodo) then name the alkane  If there are more than 2 carbons in the chain, use a number to indicate which carbon the –X group is attached to. (Number from the direction that gives the smallest number) H H Cl H C C C H H H H H Br H H H C C C C H H H 1-chloropropane 2-bromobutane

27. J Deutsch 2003 26 H OH H H C C C H H H H Naming Alcohols (-OH)  Alcohols have the hydroxyl group -OH  The prefix is the number of carbons in the longest chain –Name the alkane and drop the letter e  The suffix is ol  If there are more than 2 carbons in the chain, use a number to indicate which carbon the –OH group is attached to. (Number from the direction that gives the smallest number) H H OH H C C C H H H H 1-propanol2-propanol

28. J Deutsch 2003 27 Regents Question: 08/02 #20 Which compound is an alcohol? (1)propanal (2) ethyne (3) butane (4) methanol

29. J Deutsch 2003 28 Naming Ethers (-O-)  Ethers have an Oxygen in the chain of carbons  Name the alkyl groups on either side of the O that is in the chain  If both alkyl groups are the same it is named once with the prefix DI in front of it. H H H H C C O C H H H H Methyl ethyl ether H H H C O C H H H Dimethyl ether

30. J Deutsch 2003 29 H H O H C C C H H H Naming Aldehydes (-CHO)  Aldehydes have a double bonded Oxygen on the last carbon in the chain.  Name the alkane, drop the e and add __al propanal O H C H methanal

31. J Deutsch 2003 30 H H O H H C C C C H H H H Naming Ketones (-CO-)  Ketones have a double bonded Oxygen on a carbon in the middle of the chain. (Not the last carbon)  Name the alkane, drop the e and add __one  If there are more than 4 carbons in the chain, use a number to indicate the location of the =O butanone 3-pentanone H H O H H H C C C C C H H H H H

32. J Deutsch 2003 31 H H O H C C C OH H H Naming Organic Acids (-COOH)  Acids have a double bonded Oxygen and an –OH on the last carbon in the chain.  Name the acid, drop the e and add __oic acid Propanoic acid Pentanoic acid O H H H H HO C C C C C H H H H H H This is OH and not HO…the Carbon is bonded to the O

33. J Deutsch 2003 32 H H H C C NH 2 H H Naming Amines (-NH 2 )  Amines have a nitrogen bonded to the carbon chain. The nitrogen may have two, one or no hydrogen atoms bonded to it.  Name the alkane, drop the e and add __amine  If there are more than two carbon atoms, use a number to indicate which carbon the N is attached to. ethanamine 2-Pentanamine H NH 2 H H H H C C C C C H H H H H H

34. J Deutsch 2003 33 H O H C C OH H Name the folowing: H OH H H H H C C C C C H H H H H H H H O H H H H C C C C C C H H H H H H H O H C C H H H H H H H C C C C H H H H H H H H C C C N H H H H Ethanoic acid 1-Propanamine Ethanal 2-butene 3-hexanone 2-pentanol

35. J Deutsch 2003 34 Regents Question: 06/02 #17 Which compound is classified as a hydrocarbon? (1)Ethane (2) Ethanol (3) chloroethane (4) ethanoic acid

36. J Deutsch 2003 35 Regents Question: 06/02 #48 Which pair of compounds are alcohols?

37. J Deutsch 2003 36 Regents Question: 01/03 #49 Which type of organic compound is represented by the structural formula shown below? (1) aldehyde (2) alcohol (3) ether (4) ester

38. J Deutsch 2003 37 Isomers of organic compounds have the same molecular formula but different structures and properties. (3.1ii) H H H H H H C C C C C H H H H H H H H H C C C C H H H H H C H H Pentane C 5 H 12 Methylbutane C 5 H 12

39. J Deutsch 2003 38 Examples of isomers: 1-butanol (C 4 H 9 OH) diethyl ether (C 2 H 5 OC 2 H 5 ) propanal (C 2 H 5 CHO) 2-propanone (CH 3 COCH 3 ) 4 Carbon, 10 Hydrogen, 1 Oxygen3 Carbon, 6 Hydrogen, 1 Oxygen Isomers have the same chemical formulas but different structural formulas.

40. J Deutsch 2003 39 Regents Question: 06/03 #25 Which compound is an isomer of pentane? (1) butane (2) propane (3) methyl butane (4) methyl propane

41. J Deutsch 2003 40 Regents Question: 06/02 #19 Which formula is an isomer of butane?

42. J Deutsch 2003 41 Regents Question: 08/02 #55 Given the structural formula for butane: Draw the structural formula for an isomer of butane. H H H H C C C H H H H C H H

43. J Deutsch 2003 42 Regents Question: 01/03 #18 Which compound has an isomer?

44. J Deutsch 2003 43 In a multiple covalent bond, more than one pair of electrons are shared between two atoms. Alkenes have one double bond H C H Alkynes have one triple bond H C C H Ethene C 2 H 4 Ethyne C 2 H 2

45. J Deutsch 2003 44 Unsaturated organic compounds contain at least one double or triple bond. (5.2e) Alkenes and Alkynes are unsaturated. By breaking the multiple bond in alkenes and alkynes, more hydrogen atoms can be added Alkanes are saturated. Alkanes do not have multiple bonds, therefore, they already have as many hydrogen atoms as they could possibly hold.

46. J Deutsch 2003 45 Regents Question: 01/03 #25 In saturated hydrocarbons, carbon atoms are bonded to each other by (1) single covalent bonds, only (2) double covalent bonds, only (3) alternating single and double covalent bonds (4) alternating double and triple covalent bonds

47. J Deutsch 2003 46 Types of organic reactions include: addition, substitution, polymerization, esterification, fermentation, saponification, and combustion. (3.2c)

48. J Deutsch 2003 47 Cl Cl H C C H H Organic Reactions-Addition  Addition –H 2, Cl 2, Br 2, HCl, HBr is added to an unsaturated hyrdrocarbon. Both atoms are added to where the double (or triple) bond was located. –Key to look for – Unsaturated hydrocarbon reactant and one product. H C H + Cl 2 H C H

49. J Deutsch 2003 48 Organic Reactions- Addition Cont’d H H C C H H C H + H 2 H C H Addition of hydrogen H 2 Can be used to saturate and unsaturated hydrocarbon. It uses a catalyst such as platinum (Pt) Pt

50. J Deutsch 2003 49 Regents Question: 01/03 #26 Which formula correctly represents the product of an addition reaction between ethene and chlorine? (1)CH 2 Cl 2 (2) CH 3 Cl (3) C 2 H 4 Cl 2 (4) C 2 H 3 Cl

51. J Deutsch 2003 50 H Cl H C C H H Organic Reactions-Substitution  Substitution –A halogen is reacted with a saturated hydrocarbon. One of the halogen atoms substitutes one of the hydrogen atoms. –Key to look for – Saturated hydrocarbon reactant and two product. H H C C H H + Cl 2 UV + HCl

52. J Deutsch 2003 51 Organic Reactions- Polymerization  Polymerization – joining many small molecules together to form a large molecule –A single unit is called a monomer –Many monomers are bonded together to form a polymer –Polymers can be natural or artificial Natural PolymersArtificial Polymers ProteinPolyester RubberNylon CelluloseStyrofoam

53. J Deutsch 2003 52 Regents Question: 06/02 #49 The process of joining many small molecules into larger molecules is called (1) neutralization (2) polymerization (3) Saponification (4) substitution

54. J Deutsch 2003 53 Regents Question: 06/03 #45 Which type of reaction is represented by the equation below? Note: n and n are very large numbers equal to about 2000. (1) Esterification (3) saponification (2) fermentation (4) polymerization

55. J Deutsch 2003 54 Organic Reactions-Esterification  Esterification – making an ester by combining an alcohol with an organic acid H H C C OH H O H HO C C H H + H C C O H O H C C H H + H2OH2O

56. J Deutsch 2003 55 H H O H C C C OH H H Naming Esters (-COOC-)  Esters have a double bonded Oxygen and an –O– bonded to another carbon.  Name the alkyl group that came from the alcohol. Name the acid but drop __ic acid and replace it with ate. Propanoic acid 1-Pentanol H H H H H HO C C C C C H H H H H H Propanoic acid + pentanol Pentyl propanoate + water

57. J Deutsch 2003 56 H H O H C C C O H H H H H H H C C C C C H H H H H H H HO Propanoic acid 1-Pentanol Pentyl propanoate Making an ester by removing water from an acid and an alcohol

58. J Deutsch 2003 57 Name the ester: H O H H C C O C H H H Determine which side was the alcohol and which side was the acid by drawing a line through the oxygen in the chain. The side with the double bonded O was the acid. AcidAlcohol Alcohol will make you yl if you ate the acid. Methyl Ethanoate Methyl ethanoate

59. J Deutsch 2003 58 Regents Question: 08/02 #56 Given the ester: ethyl butanoate a. Draw the structural formula for this ester. b. Determine the gram formula mass of this ester. H H H O H C C C C O H H H H C C H H C 6 x 12 = 72 O 2 x 16 = 32 H 12 x 1 = 12 116 g Even if you got the structure wrong but you got the correct mass for the structure you drew, you got one point.

60. J Deutsch 2003 59 Amides (-CON) are made by reacting an organic acid with ammonia or with an amine. H O H H C C N C H H H H H O H C C N H H H From ammonia (NH 3 ) From amine (CH 3 NH 2 )

61. J Deutsch 2003 60 H H O H C C C OH H H Naming Amides (-CON-)  Amides have a double bonded Oxygen and a Nitrogen.  Name the alkyl group that came from the amine. Name the acid but drop __oic acid and replace it with amide. Propanoic acid 1-Pentanamine H H H H H H 2 N C C C C C H H H H H H Propanoic acid + 1-pentanamine Pentyl propanamide + water

62. J Deutsch 2003 61 H H O H C C C H H H H H H H N C C C C C H H H H H H H OH H Propanoic acid 1-Pentanamine Pentyl propanamide Making an amide by removing water from an acid and an amine

63. J Deutsch 2003 62 Amino acids have both an amine group and an acid group. An amino acid is a compound that has an amine group on one side and an acid group on the other. O R H HO C C N H H R is the only part that changes in different amino acids.

64. J Deutsch 2003 63 Proteins are polymers of amino acids O R HO C C N H H O R C C N H H H O R HO C C N H H H Remove water

65. J Deutsch 2003 64 Organic Reactions-Fermentation  Fermentation – yeast and bacteria can make ethanol and carbon dioxide by breaking down sugar using an enzyme. –The alcohol can be used to make beer and wine, –The carbon dioxide can be used to make bread rise or make the bubbles in beer and champagne. C 6 H 12 O 6 2C 2 H 5 OH + 2CO 2 Enzyme

66. J Deutsch 2003 65 Organic Reactions-Saponification  Saponification is a reaction in which a lipid (fat or oil) is used to make soap.

67. J Deutsch 2003 66 Organic Reactions-Combustion  Combustion –Burning –Combining with oxygen to produce carbon dioxide and water Burning Methane CH 4 + 2O 2 CO 2 + 2H 2 O Burning Octane 2C 8 H 18 +25O 2 16CO 2 + 18H 2 O Burning Ehtanol C 2 H 5 OH + 3O 2 2CO 2 + 3H 2 O

68. J Deutsch 2003 67 Regents Question: 08/02 #21 In which reaction is soap a product? (1) addition (2) substitution (3) Saponification (4) polymerization