Reagents

Question 1

AlBr₃

Answer 1

Aluminum Bromide

Lewis Acid (electron acceptor)

Used for: catalyst in EAS (bromination, and Friedel-Crafts)

Similar: FeCl₃, FeBr₃, AlCl₃

Question 2

AlCl₃

Answer 2

Aluminum Chloride

Lewis Acid (electron acceptor)

Used for: EAS catalyst (chlorination and Friedel-Crafts)

Similar: AlBr₃, FeBr₃, FeCl₃

Question 3

BF₃

Answer 3

Boron Trifluoride

Lewis Acid (electron acceptor)

Used for: formation of thioacetals from ketones (or aldehydes)

Similar to: FeCl₃, AlCl₃ (also Lewis Acids)

Question 4

BH₃

Answer 4

Borane

Used for: hydroboration of alkenes and alkynes.

• Hydroboration
  
  • Anti-Markovnikov (boron adds to less substituted end)
  • Syn-addition

Question 5

Br₂

Answer 5

Bromine

Used for: bromination, radical bromination

Similar to: NBS, Cl₂, I₂

1. Bromination - alkenes to vicinal dibromides​
   
   1. Anti-addition
2. Bromination - alkynes to vicinal dibromides
   
   1. trans alkenes (with excess goes to 4Br on an alkane)
3. Bromination - alkenes to halohydrins
   
   1. Markovnikov (OH on more substituted carbon)
   2. Anti-addition
4. EAS Bromination - arenes to aryl bromides
5. Radical Bromination
   
   1. ​Markovnikov

Question 6

Cl₂

Answer 6

Chlorine

Used for: chlorination, radical chlorination.

Similar to: NCS, Br₂, I₂

See reactions for Br₂

Question 7

CN^-

Answer 7

Cyanide Ion

Good nucleophile

Used for: Substitution reactions (S_N2), forming cyanohydrins from aldehydes and ketones.

AKA: KCN, NaCN, LiCN

Question 8

CrO₃

Answer 8

Chromium Trioxide

Oxidant

Used for: when pyridine is present, it is a mild oxidant that will oxidize primary alcohols to aldehydes (like PCC). If water and acid are present, chromium trioxide is strong and will oxidize the aldehyde all the way to carboxylic acid.

AKA: Na₂CrO₄, K2Cr₂O₇, Na₂Cr₂O₇, H₂CrO₄

Question 9

CuBr, CuCl, CuI

Answer 9

Copper (I) Bromide, Copper (I) Chloride, Copper (I) Iodide

Used to make organocuprates (Gilman reagents)

Question 10

DMS

Answer 10

Dimethyl Sulfide

Thioether. Often used in “reductive workup” of ozonolysis where is reduces the ozonide formed and is turned into dimethyl sulfoxide (DMSO) in the process.

AKA: Me₂S, methyl sulfide