Markovnikov addition, also called Markovnikov's rule, states that a protic acid (HX) will add to an alkene such that the proton will bond to the less substituted carbon. During this addition, the carbocation intermediate bares a positive charge on the most substituted carbon. If the reverse occurs, that is the more electronegative atom (X) ends up bonding to the least substituted carbon, it is termed anti-Markovnikov addition.
Regioselectiviy occurs in chemical reactions where one reaction site is preferred over another. For example, the addition of an asymmetric reagent (such as H-Cl) to an asymmetric alkene may yield two different products. The reaction is regioselective if one of the two products is preferred over the other. Markovnikov additions are common examples of regioselective reactions.
Nonaxial groups C n groups D n groups C nv groups C 2v C 3v C 4v C 5v C 6v C 7v C 8v C nh groups C 2h C 3h C 4h C 5h C 6h D nh groups D 2h D 3h D 4h D 5h D 6h D 7h D 8h D nd groups D 2d D 3d D 4d D 5d D 6d D 7d D 8d S n groups S 10 S 12 Cubic groups Linear groups C ∞v D ∞h
Enthalpy Δ f H (kJ) Gibbs Δ f G (kJ) Specific heat C P (J/K) Al (s) Al 2 SiO 5 (kyanite) Al 2 SiO 5 (andalusite) Al 2 SiO 5 (sillimanite) Ar (g) CH 4 (g) C 2 H 6 (g) C 3 H 8 (g) C 2 H 5 OH (l) C 6 H 12 O 6 (glucose) CO (g) CO 2 (g) H 2 CO 3 (aq) HCO 3 - (aq) Ca 2+ (aq) CaCl 2 (s) Cl 2 (g) Cl - (aq) H 2 (g) H (g) H + (aq) H 2 O (l) H 2 O (g) He (g) N 2 (g) NH 3 (g) Na + (aq) NaAlSi 3 O 8 (albite) NaAlSi 2 O 6 (jadeite) Ne (g) O 2 (g) O 2 (aq) OH - (aq) SO 4 2- (aq) HSO 4 - (aq) H 4 SiO 4 (aq)
B = e h / (4 m e ) N = e h / (4 m p ) Free electron g factor g e e = 2 g e e = -(1/2) g e m p / m e = 1836.152701 Charge-to-mass ratio for the electron e / m e c = h / (m e c) (Note that the use of brackets [ ] in the following expressions is not in accordance with standards which require the use of a slash, e.g. e = e / (2 ) (g / g e ) B e [GHz] = 13.9962 g B [T] g = 0.07144775 e [GHz] / B [T] g = 3.04199 e [GHz] / p [MHz] A [MHz] = 2.80249 (g / g e ) A [G] A [MHz] = 28.0249 (g / g e ) A [mT]
Acidities of Common Compounds at room temperature (25 o C) Hydrogen Iodide, HI (strongest acid) Sulfuric Acid, H 2 SO 4 Hydronium ion, H 3 O + Acetic Acid, CH 3 COOH Water, H 2 O Methane, CH 4 (weakest acid) pK a HA = Acetic acid H 2 A + = GlycineH + H 2 A + HA + H + H 2 A = Maleic acid H + + A 2− H 3 A = Citric acid HA = Boric acid HA H + + A − H 3 A = Phosphoric acid H 3 A H 2 A − + H + H 2 A − HA 2− + H + A 3− + H + HA − = Hydrogen sulfate H 2 A = Oxalic acid H 2 A HA − + H + HA − A 2− + H +
Chapter 2: Structure and Reactivity of Acids and Bases, Polar and Nonpolar Molecules Reactions of Alcohols with Strong Acids-Alkyloxonium Ions in Substitution and Elimination Reactions of Alcohols Chapter 9: Further Reactions of Alcohols and the Chemistry of Ethers Section 11.11: Preparation of Alkenes by Dehydration of Alcohols Section 12.3: Nucleophilic Character of the ? Bond-Electrophilic Addition of Hydrogen Halides Section 17.5: Reactivity of the Carbonyl Group-Mechanisms of Addition