ORGANIC CHEMISTRY 354ELECTROPHILIC AROMATIC SUBSTITUTIONREACTIVITYDIRECTIVE EFFECTSSYNTHESIS- REACTIVITY IN ELECTROPHILIC AROMATIC SUBSTITUTION
- METHYL GROUP ACTIVATES THE BENZENE RING TOWARDS ELECTROPHILIC AROMATIC SUBSTITUTION!
- RELATIVE RATES
- OTHER GROUPS
- *** GROUPS THAT RELEASE ELECTRON DENSITY TO THE RING ARE "ACTIVATING" GROUPS.
- *** GROUPS THAT WITHDRAW ELECTRON DENSITY FROM THE RING ARE "DEACTIVATING" GROUPS.
- *** CAN BE VIA INDUCTIVE EFFECT OR RESONANCE EFFECT.
- INDUCTIVE EFECTS
- RESONANCE EFECTS
- *** NOTE: IN SOME CASES INDUCTIVE EFFECT IS IN THE OPPOSITE DIRECTION OF THE RESONANCE EFFECT!
- ***** IN MOST CASES THE RESONANCE EFFECT IS LARGER THAN THE INDUCTIVE EFFECT (-OH, -NH2), BUT SOMETIMES RESONANCE EFFECT IS SMALLER (-Cl, -Br).
- DIRECTIVE EFFECTS IN ELECTROPHILIC AROMATIC SUBSTITUTION
- EXAMPLES
- WHY IS METHYL AN ORTHO-, PARA-DIRECTOR? answer.
- WHY IS OH AN ORTHO-, PARA-DIRECTOR?answer?, answer.
- WHY IS CHO A META-DIRECTOR?answer?, answer.
- OTHER GROUPS
- OXIDATION AND REDUCTION OF AROMATIC COMPOUNDS.
- SYNTHESIS: A -> B -> C -> D, ETC.
- HINT: ALWAYS WORK BACKWARDS!
- HOW CAN WE MAKE BENZOIC ACID FROM BENZENE?
- HOW CAN WE MAKE o-CHLOROBENZOIC ACID FROM BENZENE?
- HOW CAN WE MAKE m-CHLOROBENZOIC ACID FROM BENZENE?
| Chemistry Home | Dr. Sundin Home | sundin@uwplatt.edu |
