Chapter 17: Alcohols

Question 1

Name this compound

Answer 1

Question 2

Name this compound

Answer 2

Question 3

Name this compound

Answer 3

Question 4

Name this compound

Answer 4

Question 5

Answer 5

Question 6

What is the pKa of alcohol?

Answer 6

16

Question 7

What factors impact the acidity of alcohol?

Answer 7

1. Resonance
2. Induction
3. Substitution Effects

Question 8

Which resonance structure is more stable creating a more stable and weaker CB?

Answer 8

Question 9

Which of the following compounds are more acidic and why?

Answer 9

2,2,2-trifluoro-1-ethanol because the induction effects of fluorine increase the acidity of the alcohol

Question 10

Can OH endure substitution effects in H2O if it is in the tertiary position?

Answer 10

No, its harder to make a solvent cage for higher sub OH

Question 11

Name this reaction and draw the product

Answer 11

Hydroboration oxidation

Question 12

Name this reaction and draw the product

Answer 12

Oxymercuration/reduction

Question 13

Name this reaction and draw the product

Answer 13

Acid Catalyzed addition of water

Question 14

Name this reaction and draw the product

Answer 14

Hydroxylation

Question 15

In organic chemistry, how do we define reduction?

Answer 15

increase in C-H bonds
decrease in C-O bonds

Question 16

In organic chemistry, how do we define oxidation?

Answer 16

decrease in C-H bonds
increase in C-O bonds

Question 17

Which reagents are used to accomplish the reduction/oxidation of carbonyls?

Answer 17

Hydrides
1. Basic hydrides (Not in this section)
2. Nucleophilic hydrides

Question 18

Which nucleophilic hydrides are used to accomplish the reduction/oxidation of carbonyls?

Answer 18

Sodium Borohydride (baby hammer)
Lithium Aluminum Hydride

Question 19

What are the characteristics of Sodium Borohydride?

Answer 19

• Weak reducing agent
• Stable to water and alcohol
• attacks carbon center

Question 20

What are the characteristics of Lithium Aluminum Hydride?

Answer 20

• Strong reducing agent
• Very reactive
• pyrophoric with H2O
• Attacks carbon center

Question 21

What type(s) of alcohols are made from reducing a ketone?

Answer 21

secondary alcohol

Question 22

What type(s) of alcohols are made from reducing a aldehyde?

Answer 22

primary alcohol

Question 23

Which hydride reagents can reduce ketones and aldehydes?

Answer 23

Both sodium borohydride and lithium aluminum hydride

Question 24

Draw the product of the following reaction

Answer 24

reduction of aldehyde to primary OH

Question 25

Draw the mechanism of the following reaction

Answer 25

reduction of aldehyde to primary OH

Question 26

Draw the mechanism for the following reaction

Answer 26

Question 27

Draw the product of the following reaction

Answer 27

Question 28

What type of alcohol is made when reducing carboxylic acid?

Answer 28

primary alcohol

Question 29

What type of alcohol is made when reducing ester?

Answer 29

primary alcohol

Question 30

Is the reduction of carboxylic acids and esters more or less reactive than ketones and aldehydes?

Answer 30

Less reactive and therefore can only be reduced by lithium aluminum hydride. This reaction is a double reduction down to primary OH.

Question 31

Draw each product for a comparison chart of the carboxylic reduction reactions below

Answer 31

Question 32

Draw the product of the following reaction

Answer 32

Question 33

Draw the mechanism of the following reaction

Answer 33

Question 34

Draw the product of the following reaction

Answer 34

Question 35

Draw the product of the following reaction

Answer 35

Question 36

Draw the product of the following reaction

Answer 36

Question 37

What do Grignard reactions make?

Answer 37

new C-C bonds

Question 38

Draw the product of the following reaction

Answer 38

Question 39

Draw the mechanism of the following reaction

Answer 39

Question 40

Draw the product of the following reaction

Answer 40

Question 41

What does primary alcohol produce when oxidized?

Answer 41

aldehyde (weak, first step)
carboxylic acid (strong, second step)

Question 42

What does secondary alcohol produce when oxidized?

Answer 42

ketone

Question 43

What does tertiary alcohol produce when oxidized?

Answer 43

NO REACTION
no H bonds on attached carbon to react with

Question 44

What types of reagents are used in the oxidation of OH reactions?

Answer 44

1. Weak Oxidants
2. Strong Oxidants

Question 45

Name two weak oxidants used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones

Answer 45

1. Dess Martin Periodinase (DMP) in DCM
2. Pyrinidium chlorochromate (PCC) in DCM

Question 46

Which strong oxidant is used to oxidize primary alcohol to a carboxylic acid and secondary alcohol to a ketone?

Answer 46

Jones Reagent
Potential recipes:
1. CrO3, H2SO4, H2O
2. NaCr2O7, AcOH, H2O

Question 47

What is the name of the following reaction?

Answer 47

Acid-catalyzed dehydration of water

Question 48

Name 2 reagents that can dehydrate alcohol

Answer 48

1. H2SO4, H2O, heat
2. POCl3, Pyr, 0° (low temp kinetic control) (Phosphorus Oxychloride)

Question 49

Draw the mechanism

Answer 49

acid catalyzed dehydration

Question 50

Draw the mechanism

Answer 50

Phosphorus Oxychloride (POCl3)

Question 51

Draw the product

Answer 51