Chapter 12 Alkenes & Alkynes. Organic and BioChem

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1 hapter 12 Alkenes & Alkynes Organic and Biohem

2 Section 12.1 Introduction Unsaturated ydrocarbons ontain one or more carbon-carbon double or triple bonds 3 6? 2 2? Three lasses of Unsaturated ydrocarbons Alkenes: Alkynes: Arenes:

3 Unsaturated ydrocarbons ontain one or more carbon-carbon double or triple bonds 3 6? 2 2? Section 12.1 Introduction Three lasses of Unsaturated ydrocarbons Alkenes: ontain Double Bonds Alkynes: ontain Triple Bonds Arenes: Rings Benzene compounds (h 14)

4 Section 12.2 Structure Alkenes 3 Ethylene Propene Bond Angles?

5 Section 12.2 Alkenes Structure 3 Ethylene Propene Bond Angles? Id s with Id s with 120

6 2-butene cis-trans Isomerism cis-2-butene trans-2-butene Why a Difference?

7 cis-2-butene trans-2-butene 2-butene cis-trans Isomerism Why a Difference? NO free rotation around Double Bonds!! Only an issue when double bond is NOT terminal

8 Alkynes Ethyne (or Acetylene) Bond Angle? cis? trans?

9 Alkynes Ethyne (or Acetylene) Bond Angle? 180 cis? trans? No worries! LINEAR SAPE! There is no up or down

10 Section 12.3 Nomenclature (Naming) Double Bond: Add - ene to prefix Base prefix for longest chain that contains the double bond. ount from end closest to Double Bond Assign lowest number to double bond ARBON Double Bond cis trans Only interior double bonds Orientation of carbons in parent chain determines cis or trans IF YOU DON T KNOW DON T INLUDE!

11 Alkene Name Examples: 3 ( 2 ) 3 = =

12 Alkene Name Examples: 3 ( 2 ) 3 = 2 1-hexene = methyl-2-hexene don t know cis or trans 2-ethyl-4-methyl-1-pentene trans-3-hexene 3 3-methyl-cis-2-pentene

13 Triple Bond: Add yne to the prefix ounting rule same as double bonds 3 3 No cis or trans to worry about 3-methyl-1-butyne One new EXEPTION! Base molecule?? ommon Name is used in IUPA 2 acceptable Names Both are used. Ethyne Acetylene common used more frequently 6,6-dimethyl-3-heptyne

14 Name the following: Which could have cis/trans? 2 =( 2 ) 5 3 ( 3 ) 2 =( 3 )

15 Name the following: Which could have cis/trans? 2 =( 2 ) 5 3 ( 3 ) 2 =( 3 ) 2 1-octene 2,3-dimethyl-2-butene ,2-dimethyl-3-butyne 3,4-dimethyl-trans-2-pentene ethyl-cis-3-heptene

16 ycloalkenes Examples 3-methyl-1-cyclopentene 4-ethyl-1-methyl-1-cyclohexene Practice

17 ycloalkenes Examples 3-methyl-1-cyclopentene 4-ethyl-1-methyl-1-cyclohexene Practice 3,3-dimethyl 1-cyclohexene 1-isopropyl-4-methyl 1-cyclohexane 4-tertbutyl 1-cyclohexane

18 Dienes, trienes, and polyenes Used when multiple double bonds are found in a chain 2 = 2 = == 2

19 Dienes, trienes, and polyenes Used when multiple double bonds are found in a chain Similar rules to naming substituents are used numbers are used to Id location of double bonds di, tri, ect are used in front of ene 2 = 2 = 2 2,4-pentadiene 3 2 == 2 2-methyl-1,3-butadiene also called isoprene common name

20 omplex diene s (cis, trans) 2,4-heptadiene

21 omplex diene s (cis, trans) 2,4-heptadiene 3 trans-2-trans-4-heptadiene trans-2-cis-4-heptadiene

22 Vitamin A (retinol) Example of an all-trans alkene chain An alcohol O 3

23 Vision Molecules 11-cis-retinal (aldehyde derivative of Vitamin A) Reacts with light into All-trans-retinal O O Why is Vitamin A associated with vision? Our bodies use it as a building block for these molecules

24 3,3-dichloro-1-cyclopentene Naming examples Draw the following l l 3 2,3-dimethyl-2-butene 3 3 trans-2-pentene 2,4,4-trimethyl-2-hexene bromo-1-cyclohexene Br

25 Sec Properties: Alkenes & Alkynes ALL Non-polar compounds Only London Force intermolecular attractions Similar Properties to Alkanes Insoluble in WATER. Soluble in each other ALL less dense than water

26 Terpene Section 12.5 Terpenes Isoprene: 2-methyl-1,3-butadiene arbon #1 is the head and carbon #4 is the tail Terpenes are the most widely distributed compounds in the biological world Small subunits bonded together by catalyzed enzyme reactions Most common are essential oils used to make perfumes

27 omplex Subject: Linking Isoprene unit together

28 Section 12.6 Alkene Reactions Addition is the most common reaction Breaking and adding across the double bond! Addition of hydrogen halides Add hydrogen halides l, Br, I across the double bond to make alkyl halide alogen substituents are listed in alphabetical order along with substituents (branches) chloro, bromo, iodo ommon name is the alkyl group + followed by the name of the halide

29 Markovnikov s Rule During the addition of X to an alkene, the hydrogen will add onto the carbon that has the greatest number of s Regioselective: The addition of X is favored in one direction over another Markovnikov s rule does not explain why, it just predicts the favored result Example: Propene + Br Br Br

30 Addition of Water (ydration): Acid atalyzed Water adds across the = to form an alcohol ( and O) In the presence of an acid catalyst ( 2 SO 4 ) Draw a structural formula for the product of acid-catalyzed hydration of 1-methylcyclohexene 3 4 2SO O 2

31 ydration Examples Draw the structural formula for the product of each 2 3 alkene hydration 3 2SO4 2O 2-methyl-2-butene 4 2SO O 2

32 Addition of Bromine and hlorine arried out with pure reagents or in the presence of l 4 or 2 l 2 an be used to identify an unknown as an alkene. Br 2 is red but a dibromoalkene is colorless. 2 l 2 2l

33 Addition of ydrogen (Reduction) 2 in the presence of a metal catalyst (Pd, Ni, Pt, Ru) will add hydrogen across the double bond alled catalytic reduction or catalytic hydrogenation 3 = 3 2 Pd 2 Ni

34 Section 12.7 Polymerization of Alkenes Most important reaction of Alkenes is the formation of polymers Polymers are large molecules made of repeating monomers atalysts called initiators create the chain Structure shown by placing the repeating monomer in parentheses

35 Monomer Formula 2=2 2=3 2=l 2=l2 2=N F2=F2 2=65 2=OO23 2=OO3 xxxx ommon Name Ethylene Propylene Vinyl chloride 1,1-dichloroethylene Acrylonitrile Tetrafluoroethylene Styrene Ethyl acrylate Methyl methacrylate Polymer Name(s) ommon uses polyethylene, polythene break resistant containers polypropylene, erculon textile and carpet fibers poly vinyl chloride (PV) construction tubing poly (1,1-dichloroethylene) Saran Wrap polyacrylonitrile, Orion acrylics & acrylates polytetrafluoroethylene, PTFE Teflon, non-stick coatings polystyrene, Styrofoam insulating materials poly (ethyl acrylate) latex paints poly (methyl methacrylate), Lucite, Plexiglass: Glass substitutes

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