Organic Chemistry 1, Final Review

Based on WSU's CHEM 345

Nickname for this reagent combo: Na₂Cr₂O₇, H₂SO₄

Jones Reagent

When water is added to an acetal, what is the result?

Hydrolysis of the acetal: find the C with bonds to two Os. The water “cuts” those two C-O bonds. The O’s stay with the alcohol (or diol) they came from. The carbon becomes part of a carbonyl, which is part of the starting material.

When water is removed from an acetal, what is the result?

Dehydration of an acetal: MORE

What is an acetal?

A carbon atom bonded to 2 -OR groups (aka alkoxy groups)

Chromium (Cr) and Manganese (Mn), like in PCC or KMnO₄, are what type of agents in a reaction?

Oxidation (loss of H)

Boron (B) and Aluminum (Al) hydrides, like NaBrH₄ and LiAlH₄, are what type of agents in a reaction?

Reduction (gain of H)

True or false: Tautomers are a special type of isomers that can quickly interconvert by moving a hydrogen and a double bond.

True

What is an enol?

An alkene with a hydroxy (-OH) group

What category are these base/nucleophiles? HO^-, MeO^-, and EtO^-

Strong base, strong nucleophile

What category are these base/nucleophiles? I^-, Br^-, Cl^-, RS^-, HS^-, RSH, H₂S

Weak base, strong nucleophile

What category are these base/nucleophiles? H₂O, MeOH, EtOH

Weak base, weak nucleophile

What type of reaction(s) would you expect from the following: 1° substrate + Cl^-

SN2

What type of reaction(s) would you expect from the following: 2° substrate + EtO^-

E2 major, SN2 minor

What type of reaction(s) would you expect from the following: 3° substrate + HO^-

E2

What type of reaction(s) would you expect from the following: 1° or 2° substrate + HS^-

SN2

A bulky base (like t-ButOK) favors elimination or substitution, and what specific type?

Elimination, specifically E2