University:
Binghamton University
Course:
CHEM 231 | Organic Chemistry I
Academic year:

2024
Views:

425

Pages:

2
Author:

CrystalMintah

ACS Organic Chem Review Nomenclature Naming: Identify the parent chain (longest carbon chain) Number the chain, starting from the end closest to the substituent Name the substituents List the substituents alphabetically Use prefixes (di-, tri-, etc.) for multiple substituents of the same type Indicate the position of each substituent with a number Separate numbers from letters with hyphens and numbers from each other with commas Examples: CH₃CH₂CH₂CH₃: butane CH₃CH₂CH₂CH₂CH₃: pentane CH₃CH₂CH₂CH₂CH₂CH₃: hexane CH₃CH₂CH₂CH₂CH₂CH₂CH₃: heptane CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₃: octane Isomers: Structural isomers: Different connectivity of atoms Stereoisomers: Same connectivity, different spatial arrangement Geometric isomers (cis/trans): Same connectivity, different spatial arrangement around a double bond Enantiomers: Non-superimposable mirror images Diastereomers: Stereoisomers that are not enantiomers Practice: CH₃CH₂CH₂CH₂CH₂CH₃: hexane CH₃CH₂CH₂CH₂CH₂CH₂CH₃: heptane CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₃: octane CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₃: nonane CH₃CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₃: decane Key Differences: Alkane: Single bonds between carbon atoms Alkene: Double bond between carbon atoms Alkyne: Triple bond between carbon atoms Aromatic: Contains a benzene ring Practice: CH₃CH₂CH₂CH₂CH₂CH₃: hexane CH₃CH₂CH=CHCH₂CH₃: 2-hexene CH₃CH₂C≡CCH₂CH₃: 2-hexyne C₆H₆: benzene CH₃C₆H₅: toluene C₆H₅OH: phenol C₆H₅CH₃: toluene C₆H₅CH₂CH₃: ethylbenzene C₆H₅CH₂CH₂CH₃: n-propylbenzene C₆H₅NH₂: aniline Functional Groups: Alcohol: -OH Aldehyde: -CHO Ketone: -CO- Carboxylic acid: -COOH Ester: -COO- Amide: -CONH₂ Amine: -NH₂ Ether: -O- Practice: CH₃CH₂OH: ethanol CH₃CHO: ethanal CH₃COCH₃: propanone CH₃COOH: ethanoic acid CH₃COOCH₃: methyl ethanoate CH₃CONH₂: ethanamide CH₃NH₂: methylamine CH₃OCH₃: dimethyl ether ACS Organic Chem Review Structure Hybridization Formula FC = Ve - (B + d) where: FC: formal charge Ve: valence electrons B: bonds d: lone pairs Hybridization: sp³: 4 bonds, 0 lone pairs sp²: 3 bonds, 1 lone pair sp: 2 bonds, 2 lone pairs Carbocations: More stable carbocations have more alkyl groups attached to the positively charged carbon. Tertiary carbocations are more stable than secondary carbocations,1 which are more stable than primary carbocations. Drawing Lewis Structures Count valence electrons: Add up the valence electrons of all atoms in the molecule. Find the number of electrons needed to satisfy the octet rule: Each atom needs 8 electrons (except for hydrogen, which needs 2). Make multiple bonds or add lone pairs to fill the octet rule. Cycloalkanes Heat of combustion: Increases with ring strain. Heat of combustion per CH₂ group: Increases with ring strain. Aromaticity Rules for Aromaticity: Must be cyclic Every atom in the ring must be conjugated Molecule must have (4n+2) π electrons Molecule must be flat Acids & Bases Lewis acid: Electron pair acceptor Lewis base: Electron pair donor Any substance such as H+ that can accept a lone pair Resonance Resonance structures: Different Lewis structures that can be drawn for a molecule Resonance hybrid: The average of all resonance structures