Complete the following (answers below):

1. PCC oxidizes a primary alcohol to ________, while $K_{2}Cr_{2}O_{7}$ oxidizes it to ________.
2. The Lucas test reagent is ________ dissolved in ________.
3. A 3° alcohol shows ________ turbidity in the Lucas test.
4. Phenol has pKa ≈ ________, making it ________ acidic than ethanol (pKa ~16).
5. The Kolbe reaction converts sodium phenoxide + $CO_{2}$ → ________.
6. The intermediate in the Reimer-Tiemann reaction is ________.
7. In Williamson synthesis, the alkyl halide used must be ________ degree.
8. Phenol + $Br_{2}$/$H_{2}O$ (no catalyst) → ________.
9. -$NO_{2}$ group on phenol ________ (increases/decreases) its pKa, making it ________ acidic.
10. $NaBH_{4}$ ________ (can/cannot) reduce carboxylic acids; ________ is required instead.
11. The ease of dehydration order for alcohols is: ________ > ________ > ________.
12. Diethyl ether SMILES is ________.

Answers:

1. Aldehyde; Carboxylic acid
2. $ZnCl_{2}$; concentrated HCl
3. Immediate (within 5 min)
4. ~10; more
5. Salicylic acid (2-hydroxybenzoic acid)
6. Dichlorocarbene (:$CCl_{2}$)
7. Primary (1°)
8. 2,4,6-tribromophenol (white precipitate)
9. Decreases; more
10. Cannot; $LiAlH_{4}$
11. 3° > 2° > 1°
12. SMILES:CCOCC