Chapter 17: Alcohols Flashcards
Name this compound
Name this compound
Name this compound
Name this compound
What is the pKa of alcohol?
16
What factors impact the acidity of alcohol?
- Resonance
- Induction
- Substitution Effects
Which resonance structure is more stable creating a more stable and weaker CB?
Which of the following compounds are more acidic and why?
2,2,2-trifluoro-1-ethanol because the induction effects of fluorine increase the acidity of the alcohol
Can OH endure substitution effects in H2O if it is in the tertiary position?
No, its harder to make a solvent cage for higher sub OH
Name this reaction and draw the product
Hydroboration oxidation
Name this reaction and draw the product
Oxymercuration/reduction
Name this reaction and draw the product
Acid Catalyzed addition of water
Name this reaction and draw the product
Hydroxylation
In organic chemistry, how do we define reduction?
increase in C-H bonds
decrease in C-O bonds
In organic chemistry, how do we define oxidation?
decrease in C-H bonds
increase in C-O bonds
Which reagents are used to accomplish the reduction/oxidation of carbonyls?
Hydrides
1. Basic hydrides (Not in this section)
2. Nucleophilic hydrides
Which nucleophilic hydrides are used to accomplish the reduction/oxidation of carbonyls?
Sodium Borohydride (baby hammer)
Lithium Aluminum Hydride
What are the characteristics of Sodium Borohydride?
- Weak reducing agent
- Stable to water and alcohol
- attacks carbon center
What are the characteristics of Lithium Aluminum Hydride?
- Strong reducing agent
- Very reactive
- pyrophoric with H2O
- Attacks carbon center
What type(s) of alcohols are made from reducing a ketone?
secondary alcohol
What type(s) of alcohols are made from reducing a aldehyde?
primary alcohol
Which hydride reagents can reduce ketones and aldehydes?
Both sodium borohydride and lithium aluminum hydride
Draw the product of the following reaction
reduction of aldehyde to primary OH
Draw the mechanism of the following reaction
reduction of aldehyde to primary OH
Draw the mechanism for the following reaction
Draw the product of the following reaction
What type of alcohol is made when reducing carboxylic acid?
primary alcohol
What type of alcohol is made when reducing ester?
primary alcohol
Is the reduction of carboxylic acids and esters more or less reactive than ketones and aldehydes?
Less reactive and therefore can only be reduced by lithium aluminum hydride. This reaction is a double reduction down to primary OH.
Draw each product for a comparison chart of the carboxylic reduction reactions below
Draw the product of the following reaction
Draw the mechanism of the following reaction
Draw the product of the following reaction
Draw the product of the following reaction
Draw the product of the following reaction
What do Grignard reactions make?
new C-C bonds
Draw the product of the following reaction
Draw the mechanism of the following reaction
Draw the product of the following reaction
What does primary alcohol produce when oxidized?
aldehyde (weak, first step)
carboxylic acid (strong, second step)
What does secondary alcohol produce when oxidized?
ketone
What does tertiary alcohol produce when oxidized?
NO REACTION
no H bonds on attached carbon to react with
What types of reagents are used in the oxidation of OH reactions?
- Weak Oxidants
- Strong Oxidants
Name two weak oxidants used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones
- Dess Martin Periodinase (DMP) in DCM
- Pyrinidium chlorochromate (PCC) in DCM
Which strong oxidant is used to oxidize primary alcohol to a carboxylic acid and secondary alcohol to a ketone?
Jones Reagent
Potential recipes:
1. CrO3, H2SO4, H2O
2. NaCr2O7, AcOH, H2O
What is the name of the following reaction?
Acid-catalyzed dehydration of water
Name 2 reagents that can dehydrate alcohol
- H2SO4, H2O, heat
- POCl3, Pyr, 0° (low temp kinetic control) (Phosphorus Oxychloride)
Draw the mechanism
acid catalyzed dehydration
Draw the mechanism
Phosphorus Oxychloride (POCl3)
Draw the product
