Organic Chemistry I Workbook For Dummies, 2nd Edition
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When you're studying organic chemistry, keep these helpful reminders close by because they highlight some of the most important concepts you'll need to understand organic chemistry:

  • Electronegativity increases as you go up and to the right in the periodic table.

  • In reaction mechanisms, arrows show the movement of electrons; the tip of the arrow points to where the electrons are going.

  • Resonance is a stabilizing feature of molecules; molecular stability generally increases as the number of resonance structures increases.

  • Bronsted-Lowry acids are proton donors; Bronsted-Lowry bases are proton acceptors.

  • Strong acids have weak (stable) conjugate bases.

  • Conformation refers to the way a molecule folds itself in three-dimensional space based on the rotation around carbon-carbon single bonds; configuration (such as R or S configuration of a chiral center or cis or trans configuration of double bonds) refers to the specific orientation of atoms, which can change only through a chemical reaction.

  • Only chiral molecules have enantiomers; enantiomers rotate plane-polarized light in equal and opposite directions.

  • Molecules with chiral centers that have a plane of symmetry are called meso compounds; meso compounds are achiral.

  • In order to have diastereomers, molecules generally have to have two or more chiral centers.

  • Most organic reactions are driven by an electron-rich species (a nucleophile) attacking an electron-poor species (an electrophile).

  • Double bonds are stabilized by alkyl substituents.

  • Tertiary carbocations are more stable than secondary carbocations; secondary carbocations are more stable than primary carbocations. Allylic carbocations and benzylic carbocations are about as stable as secondary carbocations.

  • Triple bonds are shorter than double bonds; double bonds are shorter than single bonds.

  • Electrophiles are Lewis acids (electron acceptors); nucleophiles are Lewis bases (electron donors).

  • Weak bases are good leaving groups; strong bases are bad leaving groups.

  • Nucleophilicity generally parallels basicity. Typically, strong bases are also good nucleophiles.

  • Primary halides undergo SN2 substitution; tertiary halides undergo SN1 substitution.

  • Aromatics have 4n + 2 pi electrons; anti-aromatic compounds have 4n pi electrons.

  • Substituents on aromatic rings with lone pairs on the ring-attaching atom are ortho-para directors.

About This Article

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About the book author:

Arthur Winter, PhD, is a chemistry professor at Iowa State University.

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