Questions and Answers
What is a ketone?
What is an aldehyde?
What is a carboxylic acid?
What is an ester?
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What is an amide?
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What is an anhydride?
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What is an amine?
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What is an ether?
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What are constitutional isomers?
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What are stereoisomers?
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What are enantiomers?
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What are diastereomers?
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What is R configuration?
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What is S configuration?
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What functional group does a peptide bond contain?
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What functional group does a lipid contain?
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What functional groups do amino acids contain?
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What is a meso compound?
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What is the NO2 prefix?
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What is the CH=CH2 prefix?
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What is the CH2CH=CH2 prefix?
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What is phenol?
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What is benzoic acid?
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What is aniline?
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What is toluene?
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What are the three types of disubstituted benzenes?
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What is benzene?
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What happens to stability as you increase heat of combustion?
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What are Carbon 13 NMR resonances for different compounds?
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What are H 1 NMR resonances for different compounds?
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What are IR resonances for different functional groups?
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What is the difference between phenyl and benzyl?
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What is the bond angle for sp2 hybridized atoms?
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What are two key things to remember in Lewis structures?
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If a ring has a charge, then it is ____
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What does a strong acid correspond to?
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What does a double bond right next to an acidic H mean?
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What does a low pKa value indicate?
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How does hybridization relate to acidity?
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What will a hydrogen next to an electronegative atom always be?
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How do you determine if molecules are meso isomers?
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How do you find the most stable Newman projection?
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What are wedges and dashes in Fischer projections?
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If only one stereocenter is flipped in a molecule, they are...
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Do racemic mixtures get plane polarized light?
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Do meso compounds get plane polarized light?
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What can triple bonds not do stereoisomerically?
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What can an enantiomer not have?
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What happens with a dehydrohalogenation reaction?
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A strong acid corresponds to a ________ nucleophile
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Study Notes
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.
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Prepare for your ACS final exam in organic chemistry with these essential flashcards. Cover important functional groups, definitions, and key concepts in the subject. Perfect for quick revision and mastering organic chemistry terminology.
