Orgo Practice Problems Ch.10-13

Step 1: a

Step 2: c

Step 3: n/a

Step 1: a

Step 2: g

Step 3: b

Step 4: d

Step 1: a

Step 2: f

Step 3: n/a

Step 1: a

Step 2: g

Step 3: e

Step 1: a

Step 2: g

Step 3: e

Step 1: e

Step 2: n/a

Step 3: n/a

Step 1: d

Step 2: f

—>Hydroboration-Oxidation

Synthesize using benzylic bromination by NBS

Step 1: d

Step 2: f

Step 3: n/a

Synthesize using benzylic bromination by NBS

Step 1: d

Step 2: c

Step 3: n/a

Synthesize using benzylic bromination by NBS

Step 1: d

Step 2: g

Step 3: n/a

Synthesize using benzylic bromination by NBS

Step 1: d

Step 2: g

Step 3: n/a

Synthesize using benzylic bromination by NBS

Step 1: d

Step 2: c

Step 3: g

Step 1: d

Step 2: g

Step 3: n/a

Hydroboration Oxidation

Step 1: a

Step 2: c

Step 3: f

Step 1: e

Step 2: n/a

Step 3: n/a

*PBr3 specifically turns alcohols to akyl bromides!!

Step 1: b

Step 2: g

Step 3: b

Step 1: a

Step 2: b

Step 3: n/a

Step 1: b

Step 2: n/a

Step 3: n/a

Hydroboration Oxidation

Step 1: d

Step 2: n/a

Step 3: n/a

Essentially Hydroboration Oxidation

Step 1: e

Step 2: g

Step 3: n/a

Step 1: b

Step 2: f

Step 3: a

Step 1: d

Step 2: n/a

Note: SOCl2 is specifically used to convert alcohol to an alkyl chloride

Step 1: b

Step 2: n/a

Simply Hydroboration Oxidation

Step 1: a

Step 2: g

Answer: I

(LAH) reduces all carbonyl groups to alcohols

NaBH4 only reduces more reactive carbonyl groups…(aldehydes/ketones)

Jones Reagent! (CrO3 goes all the way)

Oxidation= increasing oxygen; decreasing H

IV. (COCl)2=swern oxidation “environmentally friendly” (similar to PCC)

Mg=Gringard Reagent! Strong Nucleophiles

Protection groups

Jones Oxidation

III. and IV

I. because tertiary carbocation and allylic

pi bonds must be separated by one carbon….this one is separated by two carbons

Minor meaning exo so CHO/CH3 will be pointed outwards

Major meaning endo so will be pointed downwards

Major meaning endo so facing downwards

Effect peroxide has on HBr addition

With peroxide: anti-Markovnikov

Without peroxide: Markovnikov