Cheat Sheet — OC-05 Final Rapid Review — Notes | NoteTube

Test/Reaction	Key Fact
Lucas test	3°: immediate turbidity; 2°: 5-20 min; 1°: no rxn at RT. Reagent: $ZnCl_{2}$ /conc. HCl
Oxidation	1° --[PCC]--> aldehyde; 1° --[ $KMnO_{4}$ ]--> RCOOH; 2° --[any oxid.]--> ketone; 3° → resistant
Dehydration	conc. $H_{2}SO_{4}$ , 443 K; Saytzeff: more substituted alkene; ease: 3° > 2° > 1°
Reduction	$NaBH_{4}$ reduces only aldehydes/ketones; $LiAlH_{4}$ reduces everything including RCOOH
Preparation	Acid-hydration (Markovnikov), Grignard + carbonyl, $NaBH_{4}$ / $LiAlH_{4}$

Concept	Key Fact
Acidity	pKa ~10 >> alcohol pKa ~16-18; phenoxide stabilized by resonance (5 structures)
Substituent effects	- $NO_{2}$ → more acidic (EWG); - $CH_{3}$ → less acidic (EDG)
Bromination	$Br_{2}$ / $H_{2}O$ → 2,4,6-tribromophenol (white ppt); NO catalyst needed
Kolbe reaction	P $hO^{-}$$Na^{+}$ + $CO_{2}$ → (125°C, 4-7 atm) → salicylic acid (ortho-COOH) `SMILES:OC(=O)c1ccccc1O`
Reimer-Tiemann	PhOH + $CHCl_{3}$ /NaOH → salicylaldehyde (ortho-CHO) via : $CCl_{2}$ `SMILES:O=Cc1ccccc1O`
Esterification	PhOH + $CH_{3}$ COCl → phenyl acetate `SMILES:CC(=O)Oc1ccccc1`

Concept	Key Fact
Williamson synthesis	$RO^{-}$$Na^{+}$ + R'X (MUST be 1°) → R-O-R' + NaX (SN2)
Why 1° only	2°/3° halides give E2 elimination with strong alkoxide base
HI cleavage	R-O-R' + excess HI → RI + R'I (both alkyl iodides)
Diethyl ether	`SMILES:CCOCC`; anhydrous conditions needed for Grignard

PCC = stops at aldehyde (never goes to acid); $KMnO_{4}$ = complete oxidation
Williamson = 1° halide only (3° halide → elimination, not ether)
Phenol bromination needs NO catalyst (contrast: benzene bromination needs $FeBr_{3}$ )