Named Reactions & Reagents Formula Sheet

Reaction Name	Reagents	Starting Material	Product	Key Feature
Markovnikov Addition	HX (no peroxide)	Alkene	More substituted alkyl halide	Ionic; stable carbocation
Kharasch Effect	HBr + ROOR (peroxide)	Alkene	Less substituted alkyl halide	Radical; ONLY HBr
Free Radical Halogenation	$X_{2}$ / hν or $\Delta$	Alkane	Alkyl halide	Chain: Init→Prop→Term
Ozonolysis (reductive)	$O_{3}$ then Zn/ $H_{2}O$	Alkene	Aldehydes + Ketones	Locates C=C position
Lindlar Reduction	$H_{2}$ , Pd/CaC $O_{3}$ , Pb(OAc)_{2}, quinoline	Alkyne	cis-Alkene	Syn-addition, partial
Birch (alkyne)	Na, liq. $NH_{3}$	Internal alkyne	trans-Alkene	Anti-addition, radical anion
Acetylide Formation	NaN $H_{2}$	Terminal alkyne RC≡CH	Sodium acetylide RC≡ $C^{-}$$Na^{+}$	Acidity of sp C–H

General molecular formulas:

$\text{Alkane: } C_nH_{2n+2}$

$\text{Alkene: } C_nH_{2n}$

$\text{Alkyne: } C_nH_{2n-2}$

Acidity and s-character relationship:

$\text{s-character: sp}^3 = 25\%, \quad sp^2 = 33.3\%, \quad sp = 50\%$

$\text{Acidity order: alkyne (pK}_a \approx 25) > \text{alkene (pK}_a \approx 44) > \text{alkane (pK}_a \approx 50)}$