Chapter 17: Alcohols Flashcards by serena beirold

Q

Name this compound

A

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Q

Name this compound

A

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Q

Name this compound

A

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Q

Name this compound

A

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Q

A

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Q

What is the pKa of alcohol?

A

16

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Q

What factors impact the acidity of alcohol?

A

Resonance
Induction
Substitution Effects

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Q

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

A

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Q

Which of the following compounds are more acidic and why?

A

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

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Q

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

A

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

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Q

Name this reaction and draw the product

A

Hydroboration oxidation

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Q

Name this reaction and draw the product

A

Oxymercuration/reduction

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Q

Name this reaction and draw the product

A

Acid Catalyzed addition of water

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Q

Name this reaction and draw the product

A

Hydroxylation

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Q

In organic chemistry, how do we define reduction?

A

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

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Q

In organic chemistry, how do we define oxidation?

A

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

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Q

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

A

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

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Q

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

A

Sodium Borohydride (baby hammer)
Lithium Aluminum Hydride

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Q

What are the characteristics of Sodium Borohydride?

A

Weak reducing agent
Stable to water and alcohol
attacks carbon center

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Q

What are the characteristics of Lithium Aluminum Hydride?

A

Strong reducing agent
Very reactive
pyrophoric with H2O
Attacks carbon center

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Q

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

A

secondary alcohol

Q

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

A

primary alcohol

Q

Which hydride reagents can reduce ketones and aldehydes?

A

Both sodium borohydride and lithium aluminum hydride

Q

Draw the product of the following reaction

A

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?

1. Weak Oxidants 2. Strong Oxidants

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

1. Dess Martin Periodinase (DMP) in DCM 2. 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

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

Draw the mechanism

acid catalyzed dehydration

Draw the mechanism

Phosphorus Oxychloride (POCl3)

Draw the product