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Alkenes
Pure Hydrogen Carbon with at least 1 double bond
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Boiling Point increases by 20-30 degrees
Add 1 carbon to a straight chain molecule
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Dipole Moment
The greater the dipole moment the more polarity, thus the greater the BP
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Entegen-Zusamen
- Similar to Trans-Cis
- Used in a molecule with 3 or more large groups
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Dienes
2 double bonds in a molecule
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Rules to have Cis or Trans in an Alkene
- 1) C=C
- 2) 2 large groups- 1 each on adjacent carbons
- 3) 2 Hydrogens- must be on the double bond carbons
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Functional group in an Alkene
The double bond
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Trans in a molecule
is more stable
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To determin E-Z with large groups
- He who has the greater atomic number is considered the larger group.
- Ties are broken by carbon substitution (more substitution = largest group).
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Carbon Substitution
Carbons bonded to anything but a Hydrogen
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To find the E-Z when given the name
- 1) Draw out the chain
- 2) Create the C=C in a box
- 3) Determine E-Z
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Cis always has a Higher ____ and Lower _____ than trnas
Boiling Point, Melting Point
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Sytzef's Rule/ Anti-Saytzef's Rule
- Poor Get Poorer- Major product
- Rich Get Poorer- Minor Product
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Dehydrohalogenation
- Synthesis
- Saytzef's rule w/ major & minor
- Poor get Poorer, Rich Get Poorer
- KOH in alcohol
- Original contains a halogen
- alKANE to alKENE
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Dehydration of Alcohol
- Synthesis
- Saytzef's rule w/ major & minor products
- Poor get Poorer, Rich Get Poorer
- H+ bonds w/ OH of alcohol creates H2O
- Starts as an alcohol creates an alkene + H2O when in acid
- AlkANE to AlkENE
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3D
- Dehydrohalogenation
- Dehydration of alcohols
- Dehalogenation of Vicinaldihalides
Synthesis of Alkenes
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Dehalogenation of Vicinal Dihalides
- Synthesis
- alKANE to alKENE
- 2 halogens on adjoining carbons
- Adds Zn
- No major/ minor
- Check for Cis/Trans
- Halogens link on to Zn (i.e. ZnX2)
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Reduction of Alkynes
- Synthesis
- alkynes to alKENES
- Saytzef's Rule w/ Major & Minor
- Poor get Poorer, Rich get Poorer
- Major- Lindlar Catylst, H2
- Minor- Na, Li, NH3
- 2 large groups on same side- lateral for Major poduct
- Check for Cis/Trans
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Lindlar Catylst
Creates 2 large groups on same side
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SAC
Reactions of Alkenes
- SAC-
- Substitutions
- Additions
- Cleavage
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SE//AM
- SE- Saytzef's Elimination
- AM- Addition Markovnikov
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Addition of Hydrogen
- Addition of Hydrogen in Pt, Pd, Ni
- Markovnikov, Rich get Richer, Poor get Richer
- alKENE to alKANE
- + is currency
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Addition of Halogens
- Reaction
- Markovnikov w/ major & minor products
- Rich get richer, poor get richer
- alKANE to alKENE
- Addition of X2 in CD4 (CCl4)
- Richer in +
- Halogen splits into + and -
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Addition of Hygrogen Halides
- Reaction
- Markovnikov, Major & Minor
- Rich get richer, poor get poorer
- Richer in +
- alKENE to ALKANE
- Hydrogen (+) and Group 7 (-)
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Addition of Sulfuric Acids
- Reaction
- Markovnikov, Major & Minor
- Rich get richer, poor get richer
- HSO4
- alKENE to alKANE
- H+ and HSO4-
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Addition of Water/ Hydrate Alcohols
- Reaction
- Markovnikov, Major & Minor
- Rich get Richer, Poor get Poorer
- Richer in +
- Reaction of alKENE in H20 (H+ and OH-)
- alKENE to alKANE
- Creates an alcohol side group
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Halohydration
Halohydrin Formation
- Reaction
- Markovnikov, Major & Minor
- Rich get richer, poor get richer
- H20 and Halogen (Group 7)- X+ and OH- attach
- alKENE to alcohol alKANE
- richer in +
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Alkylation
- Reaction
- Markovnikov, Major & Minor
- Rich get richer, poor get poorer
- Alcohol in acid
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Oxymercuration
- Reaction
- Major product only
- Creates an alcohol alKANE
- H20 + Hg(OAc)2
- OH attaches to + charged C
- Large group leaves becomes H
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Cations=more stable= warms faster
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Hydroboration-Oxidation
- Reaction
- Minor product only but it is Rich gets Richer
- (BH3)2 = Diborane in H20
- H+ and OH- attach
- alKENE to alcohol alKANE
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Hydroxylation
- Reaction
- Major (Hot) and Minor (Cold)
- Major- KMn04, Hot, Conc, aldahide,
- Minor- KMn04, cold dilute, alcohol
- if you make an aldahide, put an O btwn H & C and make an oic acid
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In Hydroxlyation major product-
- Break the alkene bond and replace with double bond O on carbon
- If this creates an aldahide, put an O btwn H &C and create an Oic Acid
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Ozonolysis
- Cleavage Reaction
- Major- KMnO4, Hot, conc- break the alkene bond add = O to carbons
- Minor- O3, Break the alkene bond and add = O to carbons
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Reverse Ozonolysis
Replace the double bond where the carbons are split with = O
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Halogenation
- Substitution Reaction
- Benzylic Alpha Allylic (Baa)
- Halogen reacting in heat
- Halogen replaced Hydrogen at opposite end of double bond
- X-C-C=C
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Diene
Hydrocarbon with 2 double bonds
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Isolated Diene
double bonds on opposite ends of each other
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Cumulated Diene
- double bonds on carbons next to each other
- 1 carbon has 2 double bonds
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Conjugate Diene
- C=C-C=C-C
- Double bond skips a carbon
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Diene that participates in 1,2 or 1,4 addition
- Conjugated
- Major Products Only, Rich get richer
- HBR
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