Chapter 11 Unsaturated Hydrocarbons Alkenes and Alkynes

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1 1 Chapter 11 Unsaturated ydrocarbons Alkenes and Alkynes

2 Saturated ydrocarbons 2 Saturated hydrocarbons have the maximum number of hydrogen atoms attached to each carbon atom are alkanes and cycloalkanes with single C C bonds C 3 C 2 C 3

3 Unsaturated ydrocarbons 3 Unsaturated hydrocarbons have fewer hydrogen atoms attached to the carbon chain than alkanes are alkenes with double bonds the three groups bonded to carbon atoms in a double bond are at 120 angles alkenes are flat because the atoms in a double bond all lie in the same plane are alkynes with triple bonds the two groups bonded to each carbon in a triple bond are at 180 angles Ball-and-stick models of ethene and ethyne show functional groups of double or triple bonds and bond angles.

4 Ethene (Ethylene) 4 Ethene, or ethylene, is the simplest alkene, with the formula C 2 4 has two carbon atoms connected by a double bond has two atoms bonded to each C atom is flat, with all the C and atoms in the same plane is part of a plant hormone used to accelerate the ripening of fruits C 2 = C 2 C C

5 Ethyne (commercially known as Acetylene) 5 The simplest alkyne is ethyne, which has the common name of acetylene. Acetylene is a fuel used in welding C C

6 ydrocarbon chains: alkanes, alkenes and alkynes 6 NUMBER OF CARBON ATOMS ALKANE NAME ALKENE NAME ALKYNE NAME 1 Methane Ethane Ethene Ethyne 3 Propane Propene Propyne 4 Butane Butene Butyne 5 Pentane Pentene Pentyne 6 exane exene exyne 7 eptane eptene eptyne 8 Octane Octene Octyne 9 Nonane Nonene Nonyne 10 Decane Decene Decyne

7 Learning Check 7 Identify the organic family for each: A. C 3 C 2 C=C 2 B. C. C 3 C C D.

8 Solution 8 Identify the organic family for each: A. C 3 C 2 C=C 2 alkene B. cycloalkane (alkane) C. C 3 C C alkyne D. aromatic

9 Naming Alkenes and Alkynes 9 When the carbon chain of an alkene or alkyne has four or more C atoms, number the chain to give the lowest number to the first carbon in the double or triple bond. C 2 =C C 2 C C 3 C=C C C 3 C 2 C C C butene 2-butene 2-pentyne

10 Guide to Naming Alkenes and Alkynes 10

11 Naming Alkenes 11 Using the IUPAC system, name the following compounds: C 3 C 3 C 3 C 3 C C=C 2 C 2 =C C 2 C C 3 Step 1 Name the longest carbon chain that contains the double bond. Use the ending ene for alkenes. C 3 C 3 C 3 C 3 C C=C 2 C 2 =C C 2 C C 3 butene pentene

12 Naming Alkenes 12 Step 2 Number the longest carbon chain starting from the end nearer the double bond. C 3 C 3 C 3 C 3 C C=C 2 C 2 = C C 2 C C 3 1-butene 1-pentene Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the alkene name. C 3 C 3 C 3 C 3 C C=C 2 C 2 =C C 2 C C 3 3-methyl-1-butene 2,4-dimethyl-1-pentene

13 Naming Alkynes 13 Using the IUPAC system, name the following compound: C 3 C 3 C C C C C 3 Step 1 Name the longest carbon chain that contains the triple bond. Use the ending yne for alkynes. C 3 C 3 C C C C C 3 pentyne

14 Naming Alkynes 14 Step 2 Number the longest carbon chain starting from the end nearer the triple bond. C 3 C 3 C C C C C 3 1-pentyne Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the alkyne name. C 3 C 3 C C C C C 3 3,4-dimethyl-1-pentyne

15 Learning Check 15 Write the IUPAC name for each of the following: A. C 2 =C C 2 C 3 B. C 3 C=C C 3 C 3 C. C 3 C=C C 3 D. C 3 C C C 3

16 Solution 16 Write the IUPAC name for each of the following: A. C 2 =C C 2 C 3 1-butene B. C 3 C=C C 3 2-butene C 3 C. C 3 C=C C 3 2-methyl-2-butene D. C 3 C C C 3 2-butyne

17 Learning Check 17 Write the IUPAC name for each of the following: A. C 3 C 2 C 2 C C C 3 C 3 B. C 3 C 2 C=C C 3

18 Solution 18 Write the IUPAC name for each of the following: A. C 3 C 2 C 2 C C C 3 2-hexyne C 3 B. C 3 C 2 C=C C 3 3-methyl-2-pentene

19 Cis and Trans Isomers 19 In an alkene, the double bond is rigid holds attached groups in fixed positions makes cis trans isomers possible

20 Cis Trans Isomers 20 In cis trans isomers, there is no rotation around the double bond in alkenes groups attached to the double bond are fixed relative to each other You can make a double bond with your fingers with both thumbs on the same side or opposite from each other

21 Cis Trans Isomers 21 Two isomers are possible when the groups attached to each side of the double bond are different. In a cis isomer, the alkyl groups are attached on one side of the double bond and atoms are on the other side. In the trans isomer, the groups and atoms are attached on opposite sides. BrC 3 C C Br C 3 Br C 3 C C C Br 3 cis isomer trans isomer Ball-and-stick models of the cis and Copyright trans 2012 isomers by Pearson of Education, 2-butene. Inc.

22 Cis Trans Isomerism 22 Alkenes cannot have cis trans isomers if a carbon atom in the double bond is attached to identical groups. identical C C Br Br C C C 3 Br 2-Bromopropene 1,1-Dibromoethene (not cis or trans) (not cis or trans) identical These alkenes do not have cis-trans isomers

23 Naming Cis Trans Isomers 23 The prefix of cis or trans is placed in front of the alkene name when the compound is a cis or trans isomer. Br cis Br Br trans C C C C Br cis-1,2-dibromoethene trans-1,2-dibromoethene

24 Learning Check 24 Name each, using cis or trans prefixes when needed. Br Br A. C C C 3 B. C C C 3 C 3 Cl C. C C Cl

25 Solution 25 Name each, using cis or trans prefixes when needed. A. Br C C Br cis-1,2-dibromoethene B. C 3 C C trans-2-butene C 3 C 3 Cl C. C C Cl 1,1-dichloropropene Not a cis-trans isomer

26 26 Rules for naming cyclic hydrocarbons 1. Name it as alkane or alkene according to number of carbons in the cyclic structure 2. Use word cyclo in front 3. Multiple attachments are named in alphabetical order 4. Cycloalkanes require no location number for a single attachment 5. Double bonded carbons always get numbers 1 and 2 6. Cycloalkenes attachments closest to the C=C are numbered after. 7. C66 (aromatic compound) is called benzene

27 Naming Cyclic ydrocarbons 27 Name the following ydrocarbons: Br I C2-C3 Cl C2-C3 C3 C2-C3

28 Naming Cyclic ydrocarbons 28 Name the following ydrocarbons: Br I C2-C3 Ethyl Cyclohexane Cl 1-bromo, 2-chloro Cyclopentane 1,2 dimethyl Cyclobutane C2-C3 1-ethyl Cyclopentene 3-ethyl, 1-methyl Cyclobutene Cyclohexene benzene C3 C2-C3 1-ethyl, 5-methyl Cyclohexene

29 Example of Naming Cycloalkenes Problem: Name this cycloalkene Parent chain = 8 (cyclooctene) Which way to number? double bond gets 1, 2 3, 4, 8 or 3, 7, 8 (closest to C=C) Branches? 3 branches: one ethyl and two methyl (use prefix di for the two methyls) Alphabetize : 8 - ethyl - 3, 4 - dimethyl Name: 8-ethyl-3, 4-dimethylcyclooctene

30 Chemical Reactions of Alkenes and alkynes: Addition Reactions 30 In alkene and alkynes, the double or triple bond is easily broken, providing electrons to form new bonds double and triple bonds are very reactive in addition reactions, reactants are added to the carbon atoms in the double or triple bond Three types of chemical reactions: ydrogenation alogenation ydration

31 ydrogenation 31 In hydrogenation, hydrogen atoms add to the carbon atoms of a double bond or triple bond a catalyst such as Pt or Ni is used to speed up the reaction Pt 2 C C C C 2 C 3 C 3 2 C C Ni C C C 3 C 3

32 ydrogenation of Oils 32 Adding 2 to double bonds in vegetable oils produces ydrogenated compounds with higher melting points These compounds are solids at room temperature, such as margarine, soft margarine, and shortening

33 Learning Check 33 Write an equation for the hydrogenation of 1-butene using a platinum catalyst.

34 Solution 34 Write an equation for the hydrogenation of 1-butene using a platinum catalyst. Pt C 2 =C C 2 C C 3 C 2 C 2 C 3

35 Learning Check 35 Write the product of each of the following reactions: Pt a) C 3 C=C C b) + 2 Pt

36 Solution 36 Write the product of each of the following reactions: Pt a) C 3 C=C C C 3 C 2 C 2 C 3 b) + 2 Pt

37 alogenation Reactions 37 In halogenation reactions, halogen atoms such as chlorine or bromine add across a double bond the reaction occurs without a catalyst a dihaloalkane product results In the general equation for halogenation, X 2 is used for either Cl 2 or Br 2.

38 alogenation Reactions 38 The addition reaction of Br 2 across a double bond is used to test for the presence of double bonds. A positive result turns a clear solution red.

39 Example of alogenation of Alkenes C 2 =C-C 2 -C 2 -C 3 + Br 2 Problem: What is the product of the above reaction? alogenation adds the two halogen atoms into the double bond, by removing the double bond and replacing it with a single bond 1,2-dibromopentane Br Br C 2 = C-C 2 -C 2 -C 3 + Br 2 C 2 - C-C 2 -C 2 -C 3

40 Symmetrical and Unsymmetrical Alkenes: Markovnikov s Rule Symmetry in Alkenes: A symmetrical alkene has the same number of hydrogen atoms attached to each carbon of the double bond An unsymmetrical alkene does not have the same number of hydrogen atoms attached to each carbon of the double bond Markovnikov s Rule applies to unsymmetrical alkenes It decides how a compound that has two non-identical atoms (i.e. -X or -O) is added to an unsymmetrical double bond Markovnikov s Rule states that the hydrogen adds to the carbon that has the most hydrogens on it

41 Reactions of Alkenes: ydrohalogenation ydrohalogenation An alkene reacts with a hydrogen halide (X = F, Cl, Br or I) The product of the reaction is a halogenated hydrocarbon (an alkyl halide) When the alkene is unsymmetrical, Markovnikov s Rule applies

42 Example of ydrohalogenation of Alkenes C 2 =C-C 2 -C 2 -C 3 + Br Problem: What is the product of the above reaction? ydrohalogenation adds a hydrogen and a halogen into the double bond by removing it and replacing it with a single bond. If alkene is unsymmetrical: the hydrogen adds to the carbon of the double bond that has the most hydrogens on it Br C 2 =C-C 2 -C 2 -C 3 + Br C 3 -C-C 2 -C 2 -C 3 2-bromopentane

43 ydration 43 In the addition reaction called hydration, an acid + catalyst is required water ( O) adds to a double bond an atom bonds to one C in the double bond an O bonds to the other C an alkene is converted to an alcohol + O C 3 C=C C 3 + O C 3 C C C 3 Alkene Alcohol

44 ydration 44 When hydration occurs with a double bond that has an unequal number of atoms, Markovnikov rule is applied the atom bonds to the C in the double bond with the more the O bonds to the C in the double bond with the fewer atoms

45 Learning Check 45 Write the product for the hydration of each of the following C 3 C 2 C=C C 2 C 3 + O C C 3 C=C C 2 C 3 + O 3. + O +

46 Solution 46 Write the product for the hydration of each of the following. C 3 C 2 C=C C 2 C 3 + -O + C 3 C 2 C 2 C C 2 C 3 O

47 Solution 47 Write the product for the hydration of each of the following. C C 3 C=C C 2 C 3 + O C 3 C 3 C C 2 C 2 C 3 O

48 Solution 48 Write the product for the hydration of each of the following O + O O Final Molecular Representation (Note that ydrogens are never shown in the skeletal form) Water 2 O is represented as O or -O in the above equation (as optional) in order to facilitate understanding of the molecular structure prior to reaction

49 Examples of Alkene Reactions 2SO4 C2=C-C2-C3 + 2O 1-butene C3 C=C-C3 + Cl C3 2-methyl 2-butene -C3 + Br 1-methyl cyclohexene

50 Examples of Alkene Reactions 2SO4 O C2=C-C2-C3 + 2O C3-C-C2-C3 1-butene 2-butanol (alcohol) C3 C=C-C3 + Cl C3 C2-C-C3 Cl C3 2-methyl 2-butene C3 2-chloro, 2-methyl butane -C3 + Br C3 Br 1-methyl cyclohexene 1-bromo, 1-methyl cyclohexane

51 Aromatic Compounds 51 Benzene is an aromatic compound a ring of six C atoms and six atoms a flat ring structure drawn with three double bonds represented by two structures because the electrons are shared among all the C atoms

52 Benzene Structure 52 Benzene has six electrons shared equally among the six C atoms is also represented as a hexagon with a circle drawn inside

53 Aromatic Compounds in Nature and ealth 53 Vanillin O C Aspirin O CO O C O C 3 OC 3 O O Ibuprofen Acetaminophen N C C 3 3 C C 3 C C 2 C 3 O C CO O

54 Naming Aromatic Compounds 54 Aromatic compounds are named with benzene as the parent chain with one side group named in front of benzene C 3 Cl methylbenzene chlorobenzene

55 Some Common Names 55 Some substituted benzene rings have common names that have been in use for many years with a single substituent use a common name or are named as a benzene derivative C 3 N 2 O toluene aniline phenol (methylbenzene) (benzenamine) (hydroxybenzene)

56 Naming Aromatic Compounds 56 When two groups are attached to the benzene ring, the ring is numbered to give the lowest numbers to the side groups. C 3 Cl O Cl Cl Cl 3-chlorotoluene 1,3-dichlorobenzene 2-chlorophenol (1-chloro, 3 methylbenzene)

57 Learning Check 57 Select the correct name for each compound. 1. Cl A. chlorocyclohexane B. chlorobenzene C. 1-chlorobenzene 2. C 3 A. 1,2-dimethylbenzene B. 1,4-dimethylbenzene C. 1,3-dimethylbenzene C 3

58 Solution 58 Select the correct name for each compound. 1. Cl B. chlorobenzene 2. C. 1,3-dimethylbenzene C 3 C 3

59 Learning Check 59 Write the structural formulas for each of the following: 1. 1,3-dichlorobenzene 2. 2-chlorotoluene

60 Solution 60 Write the structural formulas for each of the following: 1. 1,3-dichlorobenzene Cl Cl 2. 2-chlorotoluene C 3 Cl

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