Download Review

Survey
yes no Was this document useful for you?
   Thank you for your participation!

* Your assessment is very important for improving the work of artificial intelligence, which forms the content of this project

Document related concepts

Physical organic chemistry wikipedia, lookup

Marcus theory wikipedia, lookup

George S. Hammond wikipedia, lookup

Haloalkane wikipedia, lookup

Alkene wikipedia, lookup

Stille reaction wikipedia, lookup

Hydroformylation wikipedia, lookup

Strychnine total synthesis wikipedia, lookup

Alcohol wikipedia, lookup

Ene reaction wikipedia, lookup

Asymmetric induction wikipedia, lookup

Elias James Corey wikipedia, lookup

Cracking (chemistry) wikipedia, lookup

Ring-closing metathesis wikipedia, lookup

Woodward–Hoffmann rules wikipedia, lookup

Kinetic resolution wikipedia, lookup

Enantioselective synthesis wikipedia, lookup

Wolff rearrangement wikipedia, lookup

Diels–Alder reaction wikipedia, lookup

Fischer–Tropsch process wikipedia, lookup

Transcript
OUTLINE OF 2nd MIDTERM MATERIAL
Chapter 4: Alkanes (Cycloalkanes) –review from 1st midterm material




Cyclohexanes: chair and boat forms; equatorial and axial bonds of cyclohexanes
Mono-substituted cyclohexanes: equatorial substituents are more stable (1,3-diaxial
interactions); tert-butylcyclohexane
Disubstituted cyclohexanes: cis/trans-isomerism; comparison of stability (the fewer are
the axial substituents, the more stable is the disubstituted cyclohexane.
Fused rings (cis and trans decalins)
Chapter 5: Stereochemistry




Stereoisomers (drawing 3-D molecules in “wedged” and “dashed” bonds; Fischer
structures)
Enantiomers (physical properties); chirality; stereogenic (chiral) centers; racemic
mixtures
Optical activity; criteria for optical activity; R/S Configurations
Molecules with more than one stereogenic center; diastereoisomers; molecules with
chiral centers, but with a plane of symmetry (thus optically inactive, “meso” form)
Chapter 6: Understanding Organic Reactions








Types of organic reactions
Bond formation and bond cleavage (homolytic and heterolytic)
Reactive Intermediates
Bond Dissociation Energies (BDE)
Thermodynamics: Equilibria and free energy changes; enthalpy and entropy
Reaction/Energy Diagrams
Kinetics: Reaction rates
Catalysts/Enzymes
Chapter 7: Alkyl Halides – SN1 and SN2 Reactions






Nucleophiles (in their free base and anionic forms)
SN2 Reactions (stereochemical outcomes)
When site of attack is a chiral center
When site of attack is not a chiral center
Leaving Group abilities
SN1 Reactions (stereochemical outcomes)
Carbocations; factors which determine carbocation stability
Hammond Postulate
Competition between SN1 and SN2 Reactions
Conditions which favor SN2 reactions: uncrowded reaction site; strong nucleophiles;
aprotic polar solvents
Conditions which favor SN1 reactions: potential to form stable a carbocation (tertiary
alkyl halides); weak, non-ionic nucleophiles
Chapter 8: Alkyl Halides – Dehydrohalogenation (E1, and E2) Reactions






Site of attack in elimination reactions
Types of bases
Bulky, non-nucleophilic (strong) bases
Weak base nucleophiles
Regioselectivity (and stereoselectivity) in elimination reactions (Zaytzeff Rule)
Stereochemical requirements in E2 reactions (application to cyclic systems)
Competition between Nucleophilic Substitution and Elimination Reactions: SN1, E1
reactions generally occur together
Conditions which favor E2 reactions: more substituted alkyl halides (why?) –in contrast
to SN2 reactions-; bulky bases
Chapter 9: Alcohols and Ethers



Structural features of alcohols
Syntheses of alcohols through SN reactions
Reactions of alcohols
General Strategy: Converting –OH into a good LG (9.7A)
SN1 type reactions: conversions of 3o alcohols into alkyl halides (9.11A)
SN2 type reactions: Lewis acid –mediated (with SOCl2 and PBr3 -9.12)
E type reactions: dehydration of alcohols (9.8)