Beginner’s Guide to Common Hybrid Atomic Orbitals

SP Hybrid Atomic Orbitals

  • The central atom is bonded to two and only two atoms.
  • The electron states of the central atom have half 2s and half 2p character.
  • Three atoms generally form a straight line.

Common SP (linear) Atoms

  • Beryllium hydride (BeH2)   
  • Beryllium fluoride (BeF2) 
  • Carbon dioxide (CO2) 
  • Hydrogen cyanide (HCN) 
  • Acetylene (HCCH) 

SP2 Hybrid Atomic Orbitals

  • Combination of two 2p orbitals with one 2s orbital gives three SP2 hybridized orbitals.
  • These three orbitals generally lie in a plane.
  • An orbital may be filled with a single/double bond, or a single/paired electron.

Common SP2 (trigonal planar) atoms

  • Borane (BH3) 
  • Boron trifluoride (BF3) 
  • Formaldehyde (CH2O) 
  • Ketones (>C=O) 
  • Aldehydes (RCOH) 
  • Alkenes (>C=C<) 
  • Carbonate ion (CO32-) 
  • Benzene (C6H6) 
  • Graphite 
  • Fullerenes 
  • Nitrogen dioxide 
  • Ozone (O3-)
  • Sulfur dioxide (:SO2)
  • Sulfur trioxide (SO3)

SP3 Hybrid Atomic Orbitals

  • Combination of one s and three p orbitals, yielding four SP3 hybridized orbitals.
  • Generally has shape of a tetrahedron.
  • Often one or two orbital locations are filled with electron pairs (as in water).

Common SP3 (tetrahedral) atoms

  • Methane (CH4)  
  • Tetrafluoromethane (Carbon tetrafluoride) (CF4) 
  • Tetrachloromethane (Carbon tetrachloride) (CCl4) 
  • Chloromethane (Methyl chloride) (CH3Cl)
  • Ammonium ion (NH4+) 
  • Ammonia (:NH3) 
  • Phosphorous tetrafluoride (:PF3) 
  • Thionyl fluoride (:SOF2) 
  • Water (H2O) (::OH2) 
  • Sulfur difluoride (SF2) 
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Fundamentals: Common Strong and Weak Nucleophiles

@amoosari asks: is there an easier way to distinguish b/n strong nucleo/bases and weak ones?

Here are some common nucleophiles used in organic chemistry SN1, SN2, E1, and E2 reactions, sorted by strength:

  • VERY Good Nucleophiles: SH-, RS-, I-
  • Good Nucleophiles: CN-, N3-, Br-, HO-, RO-
  • Fair Nucleophiles: NH3, Cl-, F-, RCO2-
  • Weak nucleophiles: H20, ROH
  • VERY Weak Nucleophiles: RCO2H
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Fundamentals: What is a Locant?

In organic chemistry nomenclature, the locant is used to show where a functional group is attached, on the parent chain.

Let’s say we have a 5-carbon molecule with a ketone functional group. According to ketone nomenclature, the name will be pentanone. Pentan- for the 5 carbon chain, and -one for the ketone primary functional group.

But, the name pentanone doesn’t give us enough information to draw the molecule, because we don’t know where the ketone is on the carbon chain.

In this pentanone, the ketone is attached to carbon #2
In this pentanone, the ketone is attached to the middle carbon

In this example, a locant can be used to specify where the ketone is attached. The above examples can be renamed 2-pentanone (top) and 3-pentanone (bottom).

If a compound has multiple functional groups, then a locant can be used for each one:

6-bromo-2-methyl-1-hexene

In this example, locants are used to show that a Bromine is attached to carbon #6, a methyl is attached to carbon #2, and the double bond starts at carbon #1.

Not all locants are numbers! When naming amides, the locant “N” is often used.

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