Orgo 2, Exam 1 Alcohols

Question 1

Properties of alcohols (x3)

Answer 1

1. Act as Acids and Bases
2. Strong Acid/ Base to react (Not NaOH)
3. More stable than carbon chaines (ex. higher BP…)

Question 2

Phenol Properties

Answer 2

1. 1mil x more acidic than alcohols (NaOH works)

2. Very Stable due to resonance

Question 3

ARIO

Answer 3

• Atom
• Resonance
• Induction
• Orbital

Question 4

Acid Catalyzed addition

Answer 4

• Markovnikov

- Carbocation intermediate w/ rearrangement

Question 5

Mercury Catalyzed

Answer 5

• Markovnikov

- No intermediate/ rearrangement

Question 6

Hydroboration

Answer 6

• Anti- Markovnikov

- no rearrangement/ intermediate

Question 7

E1

Answer 7

• weak bases, often w/ heat
• 3>2>1
• 2 steps with C+ intermediate
  Alpha Beta rule, orientation irrelevant

Question 8

E2

Answer 8

• Strong Base only
• 3>2>1
• Zaitsev rule, H & X anti-periplanar

Question 9

SN1

Answer 9

• 3>2 no primary!
• Protic is favored
• C+ intermediate
• Racemization

Question 10

SN2

Answer 10

• 1 step process
• 1>2, No tertiary (sterics)
• strong Nu- only, APROTIC ONLY
• Inversion! stereochemistry

Question 11

Oxidation

Answer 11

Gain of electrons

Question 12

Reducing agents

Answer 12

NaBh4

LiAlH4

Question 13

H-

Answer 13

Strong, unstable base, Nu-

Question 14

Ketone —-NaBh4—->

Answer 14

secondary alcohol

Question 15

Aldehyde ——-NaBh4, ethanol, H3O+—->

Answer 15

Primary Alcohol

Question 16

Carbox. Acid ——LiAlH4, ether, H3O+——>

Answer 16

Primary Alcohol

Question 17

Ester ———LiAlH4, ether———>

Answer 17

Primary alcohol + R-OH

Question 18

Ketone (Grignard)

Answer 18

3 alcohol

Question 19

Aldehyde (Grignard)

Answer 19

2 alcohol

Question 20

Ester (Grignard)

Answer 20

3 alcohol + R- OH

Question 21

Oxidations of Alcohols: Primary

Answer 21

Aldehydes or Carboxylic Acides

Question 22

Ox. of secondary Alcohols

Answer 22

Ketones

Question 23

Ox. of Tertiary R-OH

Answer 23

NO REACTIONS!