有机化学烷烃-链烷烃导图（中英）

这是一篇关于有机化学烷烃-链烷烃导图（中英）的思维导图，链烷烃是一类有机化合物，其分子中的碳原子以单键相连形成链状结构，其余的价键都与氢原子结合。这种结构使得链烷烃成为饱和烃的一种，即分子中的碳原子已经达到了与氢原子结合的最大限度。

Ch3/4 Organic Compounds

• Cycloalkanes
  • Naming
    • alicyclic（脂环）/CnH2n
    • Steps
      • ① Find the parent
        • number in the largest substituent
          • cycloalkane/alkane
      • ② Number the substituents
      • ③ Write the name
  • Structure & stability
    • Cis-trans isomerism
      • less flexible
      • lesser conformational freedom
    • Stability: Ring Strain
      • Torsional strain (扭转张力)
        • the strain due to eclipsing of bonds between neighboring atoms
      • Steric strain（空间张力，非键张力）
        • the strain due to expansion or compression of bond angles
      • Angle strain（角张力）
        • forced to deviate from the ideal 109.5°tetrahedral value
        • the strain due to expansion or compression of bond angles
      • Heat of Combustion (燃烧热)
        • heat of 1 mol of compound burns completely with oxygen to form CO2 and H2O
  • Conformations
    • Cycloalkanes
      • Cyclopropane
        • Most strained - angle strain by C–C–C of 60°
        • torsional strain
        • Has bent bonds
        • C–H bonds are eclipsed
      • Cyclobutane
        • Has less angle strain
        • More torsional strain
        • one carbon atom is 25° above the plane
      • Cyclopentane
        • No angle strain
        • Large torsional strain
    • Cyclohexane
      • Conformations
        • Chair conformation
          • Strain-free
          • Neither angle strain nor torsional strain
        • Boat cyclohexane
          • No angle strain
          • Large number of eclipsing interactions
        • Twist-boat conformation
          • more stable than pure boat conformation
          • Nearly free of angle strain
      • Axial & Equatorial bonds/positions
        • Axial bond（直立键）（a键）
          • perpendicular to the ring
        • Equatorial bond（平伏键）（e键）
          • near the plane of the ring
      • Conformational Mobility
        • Ring-flip: Interconversion of chair conformations, resulting in the exchange of axial and equatorial positions
      • Monosubstituted
        • Substituent - more stable in equatorial than axial position
      • Disubstituted
        • Cis isomer
          • Both methyl groups on the same face of the ring
          • Compound exists in two chair conformations
        • Trans isomer
          • Methyl groups are on opposite faces of the ring
          • No 1,3-diaxial interactions
          • Ring-flipped conformation has both methyl groups axial
        • Exist almost exclusively in diequatorial conformation
• Alkanes
  • Naming
    • IUPAC system
      • ① Find parent hydrocarbon chain
        • longest continuous chain
        • with the larger number of branch points
      • ② Number the atoms
        • nearer to the second branch point
      • ③ Identify and number substituents
      • ④ Write the name as a single word
      • Tips
        • hyphens(-) → prefixes and commas(,)→ numbers
        • cite different side chains in alphabetical order
        • cite identical side chains after di-,tri-, tetra...
        • not for alphabetizing!
        • only prefix "iso-"used for alphabetizing
        • to name a branched substituent as compound
  • Structure & Stability
    • Alkane & Alkane Isomers
      • Alkanes:
        • Def: Compounds with C–C single bonds & C–H bonds
          • Saturated hydrocarbons
          • Also called aliphatic compounds
        • an alkane with more than three carbons can give more than one structure
      • Alkane Isomers
        • Straight-chain alkanes
        • Branched-chain alkanes
          • Alkanes with one or more carbon atoms connected to 3 or 4 C
        • Isomers
      • Constitutional Isomers
        • differs in how their atoms are arranged in chains
      • Condensed Structure of Alkanes
        • Condensed structure does not show bonds but lists atoms
    • Alkyl Groups
      • Prefixes are used to represent the number of other carbon atoms
        • 1°= primary carbon
        • 2° = secondary carbon
        • 3° = tertiary carbon
        • 4°= quaternary carbon
      • not stable compounds
      • named by replacing –ane with –yl
      • R → neralized organic group
  • Properties
    • Called paraffins
      • Low affinity
      • Burn in flame, producing CO2, H2O, and heat
    • Physical Properties
      • Solubility
        • Hydrophobic
      • Boiling points & melting points increase as size of alkane increases
      • Dispersion forces increase as molecule size increases, resulting in higher melting and boiling points
      • Branched alkanes
        • Lower b.p. with increased branching
        • Higher m.p. with increased branching
  • Conformations
    • Ethane
      • Stereochemistry（立体化学）
      • σ bonds
      • Bond rotation
        • conformer presentation
          • Sawhorse representation
          • Wedge-and-dash(楔形)
          • Newman projection(纽曼投影)
      • Torsional Strain（扭转张力）
      • Staggered conformation: Most stable(错位)
      • Eclipsed conformation: Least stable(重叠)
    • Other alkanes
      • Propane - eclipsed conformer -3 interactions
      • Butane
        • Anti conformation （对位交叉）
          • two larger groups stagger 180°
        • Gauche conformation （邻位交叉）
          • two larger groups stagger 60°
• Functional Groups
  • Def: Collection of atoms at a site that have a characteristic behavior in all molecules where they occur
  • Multiple Carbon-Carbon Bonds
    • Alkenes -- double bond
    • Alkynes -- triple bond
    • Arene -- alternating double & single C-C bonds
  • Singly bonded to an electronegative atom
  • a C– O double bond (Carbonyl Groups)