OH is more activating than OR. This is the kinda answer I was looking for .
towards electrophilic aromatic substitution. It’s one thing to learn about electrophilic aromatic substitution reactions of benzene itself. How Do We Know Methane (CH4) Is Tetrahedral? In one pattern, ortho- and para– products dominate, and the meta- product is an extremely minor byproduct. Examples of meta– directors include nitriles, carbonyl compounds (such as aldehydes, ketones, and esters), sulfones, electron-deficient alkyl groups, nitro groups, and alkylammoniums. How do ortho-, para- and meta– directors differ, and how could this difference affect the product distribution? Explain whether or not this Great article! Two Methods For Solving Problems, Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams), How To Determine R and S Configurations On A Fischer Projection, Optical Rotation, Optical Activity, and Specific Rotation, Stereochemistry Practice Problems and Quizzes, Introduction to Nucleophilic Substitution Reactions, Walkthrough of Substitution Reactions (1) - Introduction, Two Types of Nucleophilic Substitution Reactions, The Conjugate Acid Is A Better Leaving Group, Polar Protic?
-NO2 group is an electron withdrawing group. Selectivity between the sites is often decided by steric effects.
Polar Aprotic? I believe it should be a meta director since the carbon would be quite electrophilic due to the -I effect of the phenyl group. It’s a very small point but it would have saved me a few points on a test! Use any piece of structure drawing We call the substituents which lead to this result “meta- directors”. The group is nitro- and not nitrobenzene in this case.
Hence, NO 2 is a meta-director, as we all learned in organic chemistry.. However, the first place to start is that it has to do with the stability of the carbocation intermediate in electrophilic aromatic substitution reactions. learned in organic chemistry. More specifically, how does each substituent affect the stability of that intermediate? Regerence: B. Moodie, J.R. Penton, and K. Schofield, “Nitration and Aromatic Reactivity” Cambridge University Press, Cambridge 1971. https://www.cambridge.org/vi/academic/subjects/chemistry/chemistry-general-interest/nitration-and-aromatic-reactivity?format=PB. 7 - Lewis Structures, From Gen Chem to Org Chem, Pt. Master Organic Chemistry LLC, 1831 12th Avenue South, #171, Nashville TN, USA 37203, © Copyright 2020, Master Organic Chemistry, Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution. Fused Rings - Cis-Decalin and Trans-Decalin, Naming Bicyclic Compounds - Fused, Bridged, and Spiro, Bredt's Rule (And Summary of Cycloalkanes), The Most Important Question To Ask When Learning a New Reaction, The 4 Major Classes of Reactions in Org 1. Examples: -OH, -NH2, -Me, -F, -Cl, -Br, -I. Meta-directing: Substituents which draw electron density from the ortho and para positions, hence increasing reaction on the meta position. Why Do Organic Chemists Use Kilocalories? But once you move beyond benzene, that’s when things start getting really interesting.. Today we’ll describe the two main patterns by which substituents “direct” electrophilic aromatic substitution. Donation or withdrawal of electrons can occur via either a conjugative or an inductive effect. Examples: -CF3, -NO2, -CN.
Thus these positions are deactivated towards electrophilic aromatic substitution. 11 - The Second Law, From Gen Chem to Org Chem Pt.
Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction?
But, what if you have a Ph group as an substituent? Diels-Alder Reaction: Kinetic and Thermodynamic Control, Electrocyclic Ring Opening And Closure (2) - Six (or Eight) Pi Electrons, Regiochemistry In The Diels-Alder Reaction, "Is This Molecule Aromatic?"
Maybe they should call them, "Formal Wins" ?
In one pattern, substituents direct the reaction to give either the “ortho” (1,2) or “para” product, with a slight preference for “para” (1,4). Deactivating substituents: Reaction stops after the first substitution. Planning Organic Synthesis With "Reaction Maps", The 8 Types of Arrows In Organic Chemistry, Explained, The Most Annoying Exceptions in Org 1 (Part 1), The Most Annoying Exceptions in Org 1 (Part 2), Screw Organic Chemistry, I'm Just Going To Write About Cats, On Cats, Part 1: Conformations and Configurations, The Marriage May Be Bad, But the Divorce Still Costs Money.
4 - Chemical Bonding, From Gen Chem to Organic Chem, Pt. Save my name, email, and website in this browser for the next time I comment. – Deactivators (not halogens) are meta-directing. The Third Most Important Question to Ask When Learning A New Reaction, 7 Factors that stabilize negative charge in organic chemistry, 7 Factors That Stabilize Positive Charge in Organic Chemistry, Common Mistakes: Formal Charges Can Mislead, Curved Arrows (2): Initial Tails and Final Heads, Leaving Groups Are Nucleophiles Acting In Reverse, Three Factors that Destabilize Carbocations, Learning Organic Chemistry Reactions: A Checklist (PDF), Introduction to Free Radical Substitution Reactions, Introduction to Oxidative Cleavage Reactions, Bond Dissociation Energies = Homolytic Cleavage.
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