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Organic ChemistryMarch/April 2015
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+ [O], heat
reflux
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HalidesPrimary Carbons
Secondary Carbons
Tertiary Carbons
IMPORTANCE?? REACTIONS!!
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Substitution Reactions of Alkanes - Halogenation
CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)UV LIGHT
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
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Alkenesdouble bonded carbons - one sigma bond and one pi bond
Addition Reaction - attacks the weaker pi bond, therefore can be broken, leaving the pi bond
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Hydrogenation
CH2CHCH3 + H2 CH3CH2CH3
Ni catalyst @ 150°C
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With Halogens...
CH2CHCH3 + Cl2 CH2ClCHClCH3
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With hydrogen halides
CH2CHCH3 + HCl CH2ClCHClCH3
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With water
mechanism in GoodNotes
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Alkanes vs Alkenesalkenes 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
very high in residual C
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BenzeneC6H6
Aromatic functional group -
C6H5 (IUPAC name - phenyl)
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Polymerization
-alkenes readily undergoing addition to create long chains
mechanism for chloroethane...
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Challenge
Draw the repeating unit of polystyrene if the formula of the monomer is C6H5CHCH2
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Alcohols-OH functional group - polar - increases volatility and solubility of alkanes with similar molecular mass
most common alcohol - C2H5OH - ethanol - readily soluble in water
don’t forget your lone pairs
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Oxidation of alcohols (different than combustion)
when looking to oxidize an alcohol, use an oxidizing agent (acidified potassium dichromate)
Primary Alcohol Oxidation - two step
to an aldehyde first, then to carboxylic acid
+ [O], heat + [O], heat
reflux
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Secondary Alcohols-oxidized to ketones by a similar process
+ [O], heat
reflux
CH3CHOHCH3
propan-2-ol(CH3)2CO
propanone
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Tertiary Alcoholsnot readily oxidized undercomparable conditions
would involve breaking the carbon skeleton
LOTS OF ENERGY!!!
+ [O], heat
refluxNO RXN!!
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HalogenoalkanesSaturated, 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
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Primary Halogenoalkanes - SN2 Mechanism
Overall reaction occurs with NaOH:
CH3Cl + OH- CH3OH + Cl-
Since hydrogen atoms are small, there are no “blockers” for the carbon to defend itself
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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
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Carbon cation Stability
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Secondary Halogenoalkanes...?
What type of substitution do you think they undergo?
SN1 SN2
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Nucleophilic Substitution ReactionsOrganic 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
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Nucleophilic Substitution Reactions
Effect of Halogen on Nuc. Sub. Rxns
Two Opposing Factors to consider
1. Polarity of the C-H bond
2. Strength of the C-H bond
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Nucleophilic Substitution ReactionsPolarity - 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)
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Nucleophilic Substitution ReactionsBased on the reaction data:
Strength is more important
Relative rate of reaction - -
iodoalkanes > bromoalkanes > chloroalkanes > fluoroalkanes
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Nucleophilic Substitution ReactionsThese 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!!
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Conversion into AlcoholBromoethane 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?!?!
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Elimination ReactionsBasic reaction:
Halogenoalkane minus a hydrogen and a halogen
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Elimination Reactions
E1 Mechanism - less common
Good notes time!!
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Elimination ReactionsMore common Elimination reaction --> E2
Halogenoalkanes undergo both SN and E reactions
Nucleophilic substitution is more common
-NaOH in a warm, aqueous solution where OH- acts as a nucleophile
Elimination reactions are favored when:
NaOH is dissolved in a hot alcohol where it behaves as a base (grabbing H+ to form water)
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Condensation reactionsWhen two molecules react to form a product with the loss of a small molecule such as water, HCl, or ammonia
Also called addition-elimination reactions
Good notes time!!
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Condensation PolymersInclude:
Natural molecules such as silk and DNA
Synthetic molecules such as Nylon, Kevlar and PET - polyethylene terephthalate
Different from addition polymerization where no small molecule is released
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Esterification
Carboxylic acids and alcohols condense to form esters
Good notes time!!
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Brain Teaser
If you had a condensation polymer of an ester, what would it be called???
POLYESTERS!Good notes
time!!
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Forming Amides
Carboxylic acids and amines
Good notes time!!
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Reaction PathwaysDiagram on page 406...
Need to be able to go from one compound to the next...
+
+ [O], heat
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StereoisomerismBuild 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
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Now, you try it!
Draw and name the geometric isomers of butenedioic acid. (Be careful...there are two tricks!)
Good notes time!!
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Physical PropertiesDepend on:
Polarity
Shape or symmetry
Name these:
What intermolecular forces will these undergo?
Which will have a higher boiling point?
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Optical IsomersA carbon atom attached to four different atoms or groups is known as asymmetric or chiral
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Optical IsomersCan 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
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Plane of symmetry
Try it with your hands...
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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...
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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. Good notes
time!!
Good notes time!!
Draw 2-chlorobutane. Find the chiral carbon.
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Properties of Optical Isomers
Have identical physical and chemical properties
Except:
Optical activity
Reactivity with other chiral molecules