Organic Chemistry. Unit 10

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1 Organic Chemistry Unit 10

2 Halides Primary Carbons Secondary Carbons Tertiary Carbons IMPORTANCE?? REACTIONS!!

3 Benzene C6H6 Aromatic functional group - C6H5 (IUPAC name - phenyl)

4 Substitution Reactions of Alkanes - Halogenation CH4(g) + Cl2(g) UV LIGHT CH3Cl(g) + HCl(g) Reaction Mechanism - sequence of steps in a chemical reaction Initiation - creating the free radical Propagation - both use and produce free radicals Termination - removing free radicals from the mixture SHOW THE MECHANISM

5 Alkanes vs Alkenes alkenes undergo addition where alkanes will not different flame colors burning of alkenes is dirtier - higher C:H ratio Aromatic Compounds - Benzene Ring Highly unsaturated - very smoky flame Greenhouse gases, global warming, global dimming? very high in residual C

6 Alkenes - Electrophilic Addition double bonded carbons - one sigma bond and one pi bond Addition Reaction - attacks the weaker pi bond, therefore can be broken, leaving the sigma bond

7 Addition of Halogens CH2CHCH3 + Cl2 CH2ClCHClCH3

8 Hydrogenation Ni 150 C CH2CHCH3 + H2 CH3CH2CH3

9 Addition of hydrogen halides CH 2 CHCH 3 + HCl CH 2 ClCH 2 CH 3 This is only one possible product and maybe not the most likely Markovnikov and stability of carbocations

10 Carbocation Stability

11 Addition of water mechanism on the board

12 Polymerization alkenes readily undergoing addition to create long chains mechanism for chloroethene

13 Challenge Draw the repeating unit of polystyrene if the formula of the monomer is C 6 H 5 CHCH 2

14 Alcohols -OH functional group - polar - increases volatility and solubility of alkanes with similar molecular mass most common alcohol - C 2 H 5 OH (ethanol) - readily soluble in water don t forget your lone pairs

15 Oxidation of alcohols (different than combustion) when looking to oxidize an alcohol, use an oxidizing agent (acidified potassium dichromate, colored) Primary Alcohol Oxidation - two step to an aldehyde first, then to a carboxylic acid + [O], heat + [O], heat reflux

16 REFLUX VS DISTILLATION

17 Secondary Alcohols oxidized to ketones by a similar process + [O], heat reflux CH3CH(OH)CH3 propan-2-ol H + /Cr(VI) (CH3)2CO propanone Cr(III)

18 Tertiary Alcohols not readily oxidized under comparable conditions would involve breaking the carbon skeleton LOTS OF ENERGY!!! + [O], heat reflux NO RXN!!

19 Esterification Carboxylic acids and alcohols condense to form esters

20 Halogenoalkanes Saturated, polar molecules the carbon in this molecule is considered electron poor nucleophile - reactants that are electron rich and hence attracted to regions of electron deficiency leads to a reaction where the substitution of the halogen occurs called Nucleophilic Substitution shorthand - Sn

21 Primary Halogenoalkanes - SN2 Mechanism Overall reaction occurs with NaOH: CH 3 Cl + OH - CH 3 OH + Cl - Since hydrogen atoms are small, there are no blockers for the carbon to defend itself Use polar aprotic solvents (acetonitrile, acetone)

22 Tertiary Halogenoalkane: SN1 Mechanism The presence of 3 alkyl groups...what is happening? This is called steric hindrance - bulky carbon atoms make it difficult for an incoming group to attack the carbon atom

23 Secondary Halogenoalkanes? What type of substitution do you think they undergo? SN1 SN2

24 Nucleophilic Substitution Reactions Organic Reactions are very sloooooooooooowww Rate of reaction is important and studied heavily Experiments show that: SN1 is faster than SN2 reaction...why?? Which is the fastest rate of reaction...? (primary/secondary/tertiary?) TERTIARY > SECONDARY > PRIMARY

25 Nucleophilic Substitution Reactions Effect of Halogen on Nuc. Sub. Rxns Two Opposing Factors to consider 1. Polarity of the C-Halogen bond 2. Strength of the C-Halogen bond

26 Nucleophilic Substitution Reactions Polarity - electronegativity decreases down a group (from F to Cl to Br to I) Carbon is less and less electron deficient - less vulnerable to nucleophilic attack Strength - as bond strength decreases down the group, the breakage of this bond is easier (iodoalkane is the most reactive, fluorine is the least)

27 Nucleophilic Substitution Reactions Based on the reaction data: Strength is more important Relative rate of reaction - - iodoalkanes > bromoalkanes > chloroalkanes > fluoroalkanes

28 Nucleophilic Substitution Reactions These reactions are vital to many organic reactions Allow for different synthetic reagents to be used Conversions from halides to: Alcohol Amine Nitrile Good notes time!!

29 Conversion into Alcohol Bromoethane and NaOH --> ethanol and NaBr Class of alcohol produced will match class of halide used in reaction This will work with water, but is better with a base... WHY?!?!

30 Condensation reactions When two molecules react to form a product with the loss of a small molecule such as water, HCl, or ammonia Also called additionelimination reactions Good notes time!!

31 Stereoisomerism Build 2-butene...GO! Are all of our structures the same? 2 types of stereoisomerism Geometric - cis and trans isomers Optical isomers Geometric Isomers-occur with some constraint

32 Now, you try it! Draw and name the geometric isomers of butenedioic acid. (Be careful...there are two tricks!) Good notes time!!

33 Physical Properties Depend on: Polarity Shape or symmetry Name these: What intermolecular forces will these undergo? Which will have a higher boiling point?

34 Optical Isomers A carbon atom attached to four different atoms or groups is known as asymmetric or chiral

35 Optical Isomers Can be arranged in two different 3-D configurations that are mirror images of each other Known as optical isomerism The term refers to the way the isomers react with plane polarized light They are chiral molecules with NO plane of symmetry

36 Plane of symmetry Try it with your hands...

37 Enantiomers The two non-superimposable forms of optical isomers A mixture containing equal amounts of the two is known as a RACEMIC mixture A racemic mixture is optically inactive...

38 How do I know it's an optical isomer? Find the C atom with four different groups bonded to it. It is useful to mark the CHIRAL carbon with an asterisk. Try it!! Draw butan-2-ol. Find the chiral carbon. Mark it with an asterisk. Draw 2-chlorobutane. Find the chiral carbon. Good notes time!! Good notes time!!

39 Properties of Optical Isomers Have identical physical and chemical properties Except: Optical activity Reactivity with other chiral molecules

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