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35 Cards in this Set
- Front
- Back
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3 rules of major and minor resonance
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1. maximize octet rule
2. minimize charge separation 3. make sure charge on appropriate atom. |
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Hydrocarbons
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molecules that are only made up of hydrogens and carbons
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Alkane
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where all hydrocarbon are sp3 hybridized
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London dispersion
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Where a spontaneous induction of dipole occurs when two nonpolar molecules come together
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What characteristics make higher BP in Alkanes
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Longer chain
P surface area of molecule |
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Polycyclic alkanes
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when 2 or more rings are connected together by sharing c-atoms
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isomer
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same molecular formula but different structure of molecule
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constitutional isomer
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same molecular formula but different connectivity of atoms
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stereoisomers
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molecules that have same connectivity but different 3D spacial orientation
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MESO Compound
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has 2 or more SC that is superimposable through mirror image
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polar protic examples
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H20, CH3CH2OH, CH3SH
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polar aprotic examples
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DMSO, DMF
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Calculate delta H
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bonds broken - bonds formed
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solvolysis
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solvent acting as a reagent
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What is important about Nuc in an Sn1 reaction?
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It does not affect the rxn rate, but it affects the product distribution.
Rember Nuc in Sn1 tends to be weaker |
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Why do you want a polar protic solvent for an Sn1 reaction?
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This is because you want to stablize the carbocation. The leaving group will be surrounded by the polar protic sovent for a NUC to attack
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What does E1 stand for?
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unimolecular elimination
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What does E1 usually need?
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heat. E1 always associate with Sn1
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What reactions can give racemic mixtures?
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E1, radical halogination, Sn1
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What are some mine characteristics of E2?
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1. often occurs with Sn2
2.usually a big bulky base or strong base 3. occurs in a concerted rxn 4. must be antiperiplanar 5. usually when electrophile is hindered (branched) 6. high concentration of strong base |
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What makes a stronger acid?
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stabilization due to resonance and electronegative halogens
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Reducing agents
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NaBH4, LAH. LAH is stronger and cannot be used with a polar protic solvent
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How many steps does it take for a reduction rxn using LAH?
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two. it is too reactive. reduce carboxylic acid and ethers
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REaction of alcohol can attack where?
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top and bottom thus making it a racemic mixture
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Name 2 Grignurd Reagents
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Li, Mg
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Grignard function
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1. Can create reduce an alkyl halide into an alkane.
2. add carbons to carbonyls to form alcohol. 3. create carboxylic acid with react with CO2 |
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Never use Grignard reagent in this
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in a polar protic solvent. it will react with polar protic solvent and be killed
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Oxidizing reagents
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K2Cr2O7, H2SO4, H20
CrO3, H3O+, (CrO3, H2SO4) above will overoxidize primary alcohol PCC no water oxidize 2ndary and primary tertiary CANNOT be oxidized |
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For reaction of alcohol what is the major reaction for HX and H2SO4
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high concen of HX yields SN1
H2SO4 w/ heat will give E1 |
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Reagents to convert OH to halogens
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PBr3 sn2 mech, get inversion
SOCl2 sn2 mech, no inversion |
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Williamson Ether synthesis
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make alkoxide to attack alkyl halide
make sure it is primary or 2ndary inversion can occur |
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How to make ether using sn1
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use H2SO4 w/ heat. Then add MEOH
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Epoxide rxn with acidic reagents
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usually attack most hindered. protonate the Oxygen for a sn1 like reaction
can attack top and bottom racemic mixture |
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Epoxide reaction with basic like reagents
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Nuc attack less hindered. (sn2 inversion)
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Markounikov rule
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acidic H is added to least substituted carbon to create carbocation.
be aware there can still be shifts |
