1. 1 Organic Chemistry Chapter 24

2. Chapter 24 Organic Chemistry : 24.1 Classes of Organic Compounds 24.2 Aliphatic Hydrocarbons  Alkane  cycloalkane  Alkenes  Alkynes 24.3 Aromatic Hydrocarbon 24.4 Chemistry of Functional Groups  Alcohol, Ethers, Aldhyde and Ketones,Carboxylic acid, Esters 2

3. 24.1 Classes of Organic Compounds Organic Chemistry: is the chemistry of carbon compounds. Carbon has the ability to form long chains and ring structure. Hydrocarbons: compounds made of carbon and hydrogen only. ▫ Aliphatic Hydrocarbons: Do not contain benzene group. ▫ Aromatic Hydrocarbons: contain one or more benzene rings 3

4. 4 Common Elements in Organic Compounds

5. 5 أليفاتية عطرية Classification of Hydrocarbons

6. 24.2 Aliphatic Hydrocarbons Aliphatic hydrocarbons divided into: ▫ Alkanes: Only single covalent bonds are present, general formula C n H 2n+2, n = 1, 2, …. ▫ Cycloalkanes: alkanes whose carbon atoms are joined in rings, general formula C n H 2n, n = 3, 4, …. ▫ Alkenes: contain at least one carbon-carbon double bond, general formula C n H 2n, n = 2, 3 …. ▫ Alkynes: contain at least one carbon-carbon triple bond, general formula C n H 2n-2, n = 2, 3 …. 6

7. 24.2 Aliphatic Hydrocarbons Aliphatic hydrocarbons divided into: NameDefinitionGeneral Formula Alkane Only single covalent bonds are present C n H 2n+2 n = 1, 2, …. Cycloalkanes The carbon atoms are joined in rings C n H 2n n = 3, 4, …. Alkenes contain at least one C-C double bond C n H 2n n = 2, 3, …. Alkynes contain at least one C-C triple bond C n H 2n-2 n = 2, 3 …. 7 ألكانات ألكانات حلقيه ألكينات ألكاينات 7

8. 8 Alkanes (Paraffens) : CH 4 C2H6C2H6 C3H8C3H8 methaneethanepropane  The general formula C n H 2n+2 where n = 1,2,3,…  only single covalent bonds  Saturated hydrocarbons: because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the molecule.

9. 9 Alkanes The general formula C n H 2n +2 where n = 1,2,3,… increase

10. 10 Q: C 10 H 22 is the formula of an: a. alkane. b. alkene. c. alkyne. d. aromatic hydrocarbon. Q: A molecule with the formula C 3 H 8 is a(n): a. hexane b. propane c. decane d. butane e. ethane

11. 11 المجموعات المشتقة من الألكانات  An alkane less one hydrogen atom is an alkyl group. CH 4 CH 3 Methane (alkane) Methyl (alkyl)

12. 12 IUPAC: International Union of Pure and Applied Chemistry Alkanes Nomenclature الاتحاد الدولي للكيمياء البحتة والتطبيقية each name consist of 3 parts  prefix indicates position (1,3,…etc.), number (di, tri, tetra …etc.) and type of branches (alkyl or substituent groups)  parent indicates the length of the longest carbon chain or ring  suffix indicates the type of hydrocarbon (ane, ene, yne) basesuffixprefix What family? What substituents? How many carbons?

13. 13 1 - اختر أطول سلسلة ممكنة في الألكان ( مع التنبيه أنها قد لا تكون مكتوبة بصورة مستقيمة ). CH 3 CH 2 CHCH 2 CH 3 1234567 4-methylheptane Alkanes Nomenclature 1.The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule.

14. 14 CH 3 CHCH 2 CH 3 12345 2-methylpentane CH 3 CH 2 CHCH 3 12345 4-methylpentane 2- ابدأ بترقيم ذرات الكربون في السلسلة من الجهة الأقرب للتفرع. 2.Number in the direction that gives the smaller numbers for the locations of the branches.

15. 15 3 - في حال وجود أكثر من مجموعة متفرعة من نفس النوع، نستخدم prefixes di-, tri-, tetra-, CH 3 CH CH 2 CH 3 123456 2,3-dimethylhexane CH 3 CHCCH 2 CH 3 12 3 456 3,3-dimethylhexane يفصل الرقم عن الاسم بـ (-) ، والرقم عن الرقم بفاصلة (,) 3.Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind.

16. 16 CH 3 CHCH 2 CHCH 3 Br 4 - إذا وجد تفرع متساوي من الجهتين للسلسلة، فإننا نرقم من الجهة الأقرب للمشتق الأول في الحروف الانجليزية ( مجموعات الكيل أو أي مجموعات أخرى ) ويستثنى من الترتيب الهجائي البادئات ( ثنائي ، ثلاثي ، رباعي ). 2-bromo-5-methylhexane 4.If there is an equal branch of both sides of the series, we nomenclature from the closest to the first derivative of the letters in English alphabetically. 123456

17. 17 CH 3 CH CH 3 Br 1234 NO 2 2-bromo-3-nitrobutane 5.Use previous rules for other types of substituents. CH 2 CHCH 3 NH 2 1234 Cl 1-amino-3-chlorobutane

18. 18 Example 24.2: Give the IUPAC name of the following compound: Solution: 2,2,4-trimethylhexane

19. 19 Example 24.3: Write the structural formula of 3-ethyl-2,2-dimethylpentane Solution:

20. 20 Q: What is the IUPAC name of the following compound? 1234567 8 CH 3 CHCH 2 CHCH 2 CH 3 C2H5C2H5 CH 2 CH 3 4-ethyl-2-methyloctane Q: What is the structure of 4-methyl-2-propylhexane? 123456 CH 3 CHCH 2 CHCH 2 CH 3 C3H7C3H7

21. 21 Q: What is the IUPAC name of the following compound? Solution: 5-ethyl-2,4-dimethyloctane

22. 22 Molecular formulae: A molecular formula simply counts the numbers of each sort of atom present in the molecule, but tells you nothing about the way they are joined together. Example: the molecular formula of butane is C 4 H 10, and the molecular formula of ethanol is C 2 H 6 O. Structural formulae: A structural formula shows how the various atoms are bonded. Example: ethanoic acid (acetic acid) would be shown in a fully displayed form and simplified form as: Drawing Organic Molecules CH 3 COOH or الصيغة الجزيئية الصيغة التركيبية

23. 23 Structural isomers: are molecules that have the same molecular formula but different structural formula التشكل البنائي : هي أشكال مختلفة لمركبات لها نفس الصيغة الجزيئية ولكنها تختلف في الصيغة البنائية. Structural Isomers  متشكلات بنائيه : تكون في الالكانات ( يحفظ الجدول في الشريحه التاليه )

24. 24 Structural Isomers of Alkanes # carbonsName# isomers 1Methane1 (no isomer) 2Ethane1 (no isomer) 3Propane1 (no isomer) 4Butane2 5Pentane3 6Hexane5 7Heptane9 8Octane18 20Eicosane366,319

25. 25 CH 4 C2H6C2H6 C3H8C3H8 C 4 H 10 Structural Isomers

26. 26 Example 24.1: How many structural isomers does pentane, C 5 H 12, have? CCCC C HHHHH H HHHHH H CCC C HCH 3 HH H HHHH H CC C H H H HH H n-pentane 2-methylbutane 2,2-dimethylpropane

27. 27 Q: How many structural isomers does pentane (C 5 H 12 ) have? A. 1 B. 2 C. 3 D. 4 Solution: C 5 H 12 = C n H 2n+2 THUS: Alkane → Pentane → 3 isomers Q: Which of these species are structural isomers of C 6 H 14 ? A. I and II B. I and III C. II and III D. II and IV E. III and IV

28. 28 Cycloalkanes  Alkanes whose carbon atoms are joined in rings are called cycloalkanes.  The general formula: is C n H 2n where n = 3,4,…

29. 29 Alkenes (Olefins) CH 2 CHCH 2 CH 3 CH CH 3 2-butene1-butene  Alkenes: at lease one C-C double bond is present.  The general formula: is C n H 2n where n = 2,3,4,…  أبسط الألكينات هو الإيثين أو الإيثيلين ethene or ethylene H 2 C = CH 2  Cracking C 2 H 6 (g) CH 2 = CH 2 (g) + H 2 (g) Pt catalyst

30. سم أطول مجموعة متسلسلة كربونية تحتوي على رابطة ثنائية وابدأ بترقيم ذرات الكربون في السلسلة من الجهة الأقرب إلى الرابطة المزدوجة. 3-methyl-2-heptene 30 Alkene Nomenclature CH 2 CH 3 CHCCH 3 CH CH CH 3 Br 4-bromo-2-pentene

31. 31  إذا كانت النهايتان بنفس المسافة من الرابطة الثنائية ابدأ بالترقيم من النهاية التي يكون بقربها أول تفرع. 2-methyl-3-hexene CH 2 CHCH 3 CH CH 3 123456

32. 32 CH 2 CHCH 2 CH CH 2 Q: Name the following compound? 1,4-pentadiene  إذا كان هناك أكثر من رابطة ثنائية رقم موقعها واستخدم الدلالات التالية الدالة على عددها [ دايين ، ترايين.... ] رابطتين ثنائيتين ، ثلاث روابط ثنائية.

33. 33 Geometric Isomers of Alkenes CC Cl HH CC H H cis-dichloroethylenetrans-dichloroethylene نفس الاتجاه عكس المتشكلات الهندسيه سس وترانس ( متشكلات هندسيه ) يعني وجود مجموعات متشابه على طرفي الرابطه الثنائيه بالتالي ننظر هل هما في نفس الاتجاه ( سس ) او : في اتجاهين متعاكسين ( ترانس ) Less stable More stable

34. 34 Q: Which of the following compounds has geometrical isomer? CC HCl HH CC H H CC NO 2 Cl HH CC NO 2 Cl H CC HH NO yes cis-chloronitroethylen cis-dichloroethylene يشترط لوجود متشاكلين مختلفين أن تكون على كل من ذرتي الكربون للرابطة المزدوجة مجموعتان أو ذرتان مختلفتان ، إذ بمجرد وجود مجموعتين متشابهتين على إحدى ذرتي الكربون يصبح جانبا الجزيء متماثلين.

35. 35 Q: For which of the compounds below are cis- trans isomers possible? CH 3 CH=CH 2 CH 3 CH=CHCH 2 CH 3 CH 3 CH=CHCH 3 (1)(2)(3) only 2 both 1 and 2 both 2 and 3 all three only 3 ملحوظة : بما أن الرابطة المزدوجة عند ذرة الكربون رقم (1) ولا تحتوي على مستبدلات ( ترتبط فقط بذرات هيدروجين ) فإن الألكين لايكون متشكلات هندسية

36. 36 Q: Which of the following does NOT exhibit geometric isomerism? (Hint: draw them!) A.4-octene B.2-pentene C.3-hexene D.2-hexene E.1-hexene CH 2 CHCH 3 CHCH 3 CH 2 CC H H CH 3 CH 2 3-hexene CH 2 CH 3 CHCH 2 ملحوظة : بما أن الرابطة المزدوجة عند ذرة الكربون رقم (1) ولا تحتوي على مستبدلات ( ترتبط فقط بذرات هيدروجين ) فإن الألكين لايكون متشكلات هندسية

37. 37 1-butyne 2-butyne CH CCH 2 CH 3 CC  Alkynes: at lease one C-C triple bond is present.  The general formula: is C n H 2n-2 where n = 2,3,4,… Alkynes

38. 38 Q: Write the structural formulas for the following compounds:

39. 39 C C C CC C H H H H H H C C C CC C H H H H H H Aromatic compound: contain one or more benzene ring Aromatic Hydrocarbons Delocalized molecule orbital's x H H H H H x H H H H H Parent الأساس benzene substituent مستبدل phenyl

40. 40  Benzene is parent name: If one H atom has been replaced by another atom or a group of atom → the name of the atom or group then benzene Aromatic Hydrocarbons Nomenclature CH 2 CH 3 ethylbenzene Cl chlorobenzene NH 2 aminobenzene (aniline) NO 2 nitrobenzene الأساس

41. 41  If more than one substituent is present → we must indicate the location of the second group relative to first then benzene 1 2 3 4 5 6 Br 1,2-dibromobenzene (o-dibromobenzene) Br 1,3-dibromobenzene (m-dibromobenzene) Br 1,4-dibromobenzene (p-dibromobenzene) 1,2 ortho o- 1,3 meta m- 1,4 para p- مستبدل

42. 42 1 2 3 4 5 6 NO 2 Br 3-bromonitrobenzene (m-bromonitrobenzene) CH 3 -CH-CH 3 2-phenylpropane isopropylbenzene

43. 43 Q: Which one of these formulas is that of an unsaturated hydrocarbon? A.CH 3 – CH 2 – CH 3 B.CH 3 – CH = CH 2 C.CH 3 – CH 2 – OH Answer: B غير مشبع ( يحتوي رابطة مزدوجة أو ثلاثية )

44. Q: Which of these is the systematic name for the compound represented below? CH 3 – CH 2 – CH – CH 3 CH = CH 2 A. 2-ethylbutane B. 3-methyl-1-hexene C. 3-methyl-1-pentene Answer: C 44 12 3 45 التسمية النظامية ( أيوباك ) طالما أن المركب العضوي يحتوي رابطة مزدوجة فاختاري أطول سلسلة تحتوي هذه الرابطة وابدئي الترقيم من الجهة الأقرب للرابطة المزدوجة

45. 45 Functional Groups Groups that are responsible for most of the reactions of the parent compounds. المجموعات الوظيفية تعرف المجموعة الوظيفية بأنها مجموعة من الذرات التي تمثل الموضع المهم والنشط في التفاعلات الكيميائية للمركب الذي يحتوي عليها. 24.4 Chemistry of Functional Groups  Different Functional Groups forms: Alcohol Ethers Aldhyde Ketones Carboxylic acid Esters Amines Aminoacid

46. 46 Alcohols: contain the hydroxyl functional group and have the general formula R-OH.

47. 47 Ethers: have the general formula R-O-R’. CH 3 OCH 3 Dimethyl ether C 2 H 5 OC 2 H 5 Diethyl ether CH 3 OC 2 H 5 methyl Ethyl ether

48. 48 H C H O H C O CH 3 C O H3CH3C Aldehydes and Ketones: Contain the Carbonyl functional group  Aldehyde: has the general formula:  Ketone: has the general formula: C = O R H R R’ C = O formaldehyde methanal acetaldehyde ethanal acetone Dimethyl ketone

49. 49 Carboxylic acids: contain the carboxyl ( -COOH ) functional group.

50. 50 Esters: have the general formula R’COOR, where R is a hydrocarbon group, and R’ can be H or a hydrocarbon The odour of fruits is due to the ester compounds they contain. CH 3 COOH + HOCH 2 CH 3 CH 3 C O CH 2 CH 3 + H 2 O O ethyl acetate Carboxylic acidsAlcohols

51. 51 Amines: are organic bases with the general formula R 3 N. CH 3 NH 2 CH 3 CH 2 NH 2 Ethylamine Methylamine CH 3 CHCH 3 2-aminopropane NH 2 aminobenzene (aniline)

52. 52 Chapter 25 Synthetic and Natural Organic Polymer

53. 53 Polymers: are large molecules made up of repeating units called Monomers. Proteins: are polymers of amino acids. Termed polypeptides Play a key role in nearly all biological processes. Proteins high molar mass; ranging from about 5000 g. 25.3 Proteins

54. 54

55. 55 The basic structural unit of protein is amino acids Amino acids: are the basic structural units of proteins.  Contain at least one amino group (-NH 2 )  And at least one carboxyl group (-COOH) 25.3 Proteins Amino acid

56. 56 Amino acids: existing form is pH dependent

57. 57 Amino acids: are joined in a protein by the formation of a peptide bond + H 3 N C C N C C O - + H 2 O H R1R1 H R2R2 O O H + H 3 N C C O - + + H 3 N C C O - H R1R1 H R2R2 OO Peptide (amide) bond planar

58. 58 CompoundsFunctional group.Comments 1-alcohol R-OH 2-Ethers R-O-R’ R=R’, R≠ R’ R (Hydrocarbon, aromatic ) 3-ketone R=R’, R≠ R’ R (Hydrocarbon, aromatic ) 4-aldhyde 5-carboxilic acid 6- ester R=R’, R≠ R’ R (Hydrocarbon, aromatic ) 7- amine R3NR3N R 2 NH, RNH 2 8-Amino acid R - C - H O = R - C – R’ O = R - C - OH O = R - C – OR’ O = R-CH - C - OH O = NH 2 - Functional Group Chemistry

59. 59 Q: A protein is: A) a polymer of amino acids B) a fatty acid ester of glycerol C) a polysaccharide D) an addition polymer E) a polymer of fatty acids

60. 60 Q: Classify each of the following molecules as: alcohol, aldehyde, ketone, carboxylic acid, ether, or amino acid

61. 61 Q: The formula CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 OH represents: A. an alcohol B. an alkene C. an alkyne D. an unsaturated hydrocarbon Q: Which of the following is a ketone? A. CH 3 CH 2 COCH 3 B. CH 3 CH 2 CHO C. CH 3 OCH 3 D. CH 3 CH 2 COOH E. H 2 C=C=CH 2

62. 62 Q: Which type of functional group does not include a carbonyl group in its structure? A. carboxylic acid B. ether C. ketone D. aldehyde E. ester Q: Vanillin is used as a flavoring agent. Identify the functional group circled. A. aldehyde B. ketone C. carboxylic acid D. Alcohol C = O carbonyl

63. 63 Problems 24.3 – 24.7 – 24.14 24.2 – 24.16 – 24.26 – 24.28 – 24.32 – 24.50 24.36 – 24.42 – 24.58 – 24.60