Organic Chemistry ACS Final Exam Flashcards

Functional Groups

• Ketone: An organic compound characterized by a carbonyl group (C=O) where the carbon atom is bonded to two other carbon atoms.
• Aldehyde: Contains a carbonyl group (C=O) at the end of the carbon chain, making it highly reactive.
• Carboxylic Acid: Contains a carboxyl group (-COOH), and is known for its acidic properties.
• Ester: Formed from the reaction between an alcohol and a carboxylic acid; commonly found in fats and oils.
• Amide: Contains a carbonyl group (C=O) bonded to a nitrogen atom; formed from the condensation of an amine and a carboxylic acid.
• Anhydride: Formed from two carboxylic acids by the removal of water; frequently used in organic synthesis.
• Amine: Contains a nitrogen atom bonded to one or more alkyl or aryl groups; classified as primary, secondary, or tertiary.
• Ether: Organic compounds with an oxygen atom connected to two alkyl or aryl groups.

Isomerism

• Constitutional Isomers: Molecules with the same molecular formula but different connectivity of atoms.
• Stereoisomers: Molecules with the same molecular formula, but different spatial arrangements of atoms.
• Enantiomers: Type of stereoisomer that are non-superimposable mirror images of each other.
• Diastereomers: Stereoisomers that are not mirror images; often have different physical properties.

Configuration

• R Configuration: Clockwise arrangement of substituents around a chiral center.
• S Configuration: Counterclockwise arrangement of substituents around a chiral center.

Peptide Bond and Lipids

• Peptide Bond: Contains an amide functional group, linking amino acids in proteins.
• Lipids: Composed mainly of ester functional groups, important for storing energy.

Amino Acids

• Amino acids commonly contain aromatic rings which contribute to their chemical properties.

Meso Compound

• Contains multiple stereocenters but is superimposable on its mirror image due to internal symmetry.

Common Prefixes

• NO2: Nitro
• CH=CH2: Vinyl
• CH2CH=CH2: Allyl

Aromatic Compounds

• Phenol: A benzene ring with a hydroxyl (-OH) group.
• Benzoic Acid: An aromatic carboxylic acid with a carboxyl group attached to a benzene.
• Aniline: An aromatic amine, comprising a benzene ring and an amino group.

Benzene Derivatives

• Three types of disubstituted benzenes are ortho (1,2), meta (1,3), and para (1,4).

Stability and Energy

• Stability decreases as the heat of combustion increases; more stable compounds release less energy upon combustion.

NMR Spectroscopy

• Carbon-13 NMR Resonances:

  • 0-80: sp3 Hybridized Carbon
  • 125-150: Aromatic
  • 160-180: Esters/Acids
  • 200-220: Aldehydes/Ketones

• Proton NMR Resonances:

  • 0.9-1.5: sp3 Carbon
  • 2-2.5: Allylic Hydrogen
  • 3-4.5: O-CH3
  • 4.5-6.5: Vinylic Hydrogen
  • 7-8.5: Aromatic Hydrogen
  • 10: Aldehyde
  • 10-12: Carboxylic Acid

• Infrared (IR) Resonances:

  • 3400: OH and NH
  • 3100-3000: sp2 Carbon
  • 2100: Triple Bonds
  • 1700: Ketones
  • 1600: C=C, Aromatic C-C
  • 1500: Aromatic C-C

Additional Concepts

• Phenyl vs. Benzyl: Benzyl includes a -CH2- group linking the benzene ring to another substituent.
• Hybridization: The bond angle for sp2 hybridized carbon is approximately 120 degrees.
• Lewis Structures: Focus on achieving filled octets and placing negative charges on electronegative atoms.
• Aromatic rings with charges indicate increased aromaticity.
• A strong acid correlates with a weak base and indicates higher acidity associated with lower pKa values.
• Hybridization affects acidity; more s character in hybridized orbitals leads to greater acidity.

Stereochemistry

• Meso compounds do not rotate plane-polarized light due to symmetry.
• Racemic mixtures do not rotate plane-polarized light as well; they contain equal amounts of enantiomers.
• A hydrogen next to an electronegative atom is typically more acidic.
• Dehydrohalogenation generally results in the formation of double bonds to increase compound stability.
• Syn addition occurs when two substituents add to the same face of a double bond, while anti addition occurs on opposite faces.