Ester Prelab Quiz

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14 Terms

1
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What is the mechanism of Fischer esterification of acetic acid with benzyl alcohol?

  1. Carbonyl from acetic acid takes a proton from protonated alcohol (forms  another OH)

  2. Then the Oxygen from benzyl alcohol attacks carbonyl carbon

  3. Then the alcohol deprotonates itself

  4. OH from either esterification or acid takes proton from protonated alcohol to be a better leaving group

  5. Leaving group leaves, forming a C=O bond

  6. Then the C=OH group gets deprotonated

<ol><li><p><span>Carbonyl from acetic acid takes a proton from protonated alcohol (forms&nbsp; another OH)</span></p></li><li><p><span>Then the Oxygen from benzyl alcohol attacks carbonyl carbon</span></p></li><li><p><span>Then the alcohol deprotonates itself</span></p></li><li><p><span>OH from either esterification or acid takes proton from protonated alcohol to be a better leaving group</span></p></li><li><p><span>Leaving group leaves, forming a C=O bond</span></p></li><li><p><span>Then the C=OH group gets deprotonated</span></p></li></ol><p></p>
2
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What is the mechanism of the reaction between acetyl chloride and benzyl alcohol?

  1. Benzyl alcohol attacks carbonyl group (rate determining)

  2. Benzyl alcohol has a positive charge and oxygen has a negative charge

  3. Chloride leaves and then C=O bond reforms

  4. Chloride then deprotonates the benzyl alcohol, removing the positive charge

<ol><li><p><span>Benzyl alcohol attacks carbonyl group (rate determining)</span></p></li><li><p><span>Benzyl alcohol has a positive charge and oxygen has a negative charge</span></p></li><li><p><span>Chloride leaves and then C=O bond reforms</span></p></li><li><p><span>Chloride then deprotonates the benzyl alcohol, removing the positive charge</span></p></li></ol><p></p>
3
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What is the structure of propyl acetate?

3 carbon chain

<p>3 carbon chain</p>
4
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What is the structure of 3-methylbutyl acetate?

4 carbon chain with a methyl group on C3

<p>4 carbon chain with a methyl group on C3</p>
5
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What is the structure of octyl acetate?

8 carbon chain

<p>8 carbon chain</p>
6
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What is the structure of benzyl acetate?

1 carbon and then a benzene ring

<p>1 carbon and then a benzene ring</p>
7
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How do you synthesize acetyl chloride from acetic acid and any inorganic reagent? Show the balanced equation.

CH3COOH + SOCl2 → CH3COCl + SO2 + HCl

<p><span>CH<sub>3</sub>COOH + SOCl<sub>2</sub> → CH<sub>3</sub>COCl + SO<sub>2</sub> + HCl</span></p>
8
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What is the structure of ethyl formate?

Aldehyde with 2C ether

<p>Aldehyde with 2C ether</p>
9
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What is the structure of Ethyl Acetate?

2C Ketone with 2C ether

<p>2C Ketone with 2C ether</p>
10
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What is the structure of ethyl propionate?

Ketone with 3 carbons and 2C ether group

<p>Ketone with 3 carbons and 2C ether group</p>
11
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What is the structure of ethyl benzoate?

Ketone with benzene ring and then 2C ester

<p>Ketone with benzene ring and then 2C ester</p>
12
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What is the mechanism of the base catalyzed ester hydrolysis?

  1. In basic conditions alcohol attacks carbonyl carbon, shifting electrons to oxygen on carbonyl

  2. Then electrons on carbonyl carbon shift back, kicking off ether group

<ol><li><p><span>In basic conditions alcohol attacks carbonyl carbon, shifting electrons to oxygen on carbonyl</span></p></li><li><p><span>Then electrons on carbonyl carbon shift back, kicking off ether group</span></p></li></ol><p></p>
13
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What is the mechanism of the acid catalyzed ester hydrolysis

  1. First, the O in carbonyl takes proton from hydronium ion

  2. Then the H2O attacks carbonyl carbon

  3. H2O then gets deprotonated 

  4. Ether group gets protonated

  5. OH shifts electrons to make double bond, and then ether group leaves

  6. Finally water deprotonates OH on carbonyl

<ol><li><p><span>First, the O in carbonyl takes proton from hydronium ion</span></p></li><li><p><span>Then the H<sub>2</sub>O attacks carbonyl carbon</span></p></li><li><p><span>H<sub>2</sub>O then gets deprotonated&nbsp;</span></p></li><li><p><span>Ether group gets protonated</span></p></li><li><p><span>OH shifts electrons to make double bond, and then ether group leaves</span></p></li><li><p><span>Finally water deprotonates OH on carbonyl</span></p></li></ol><p></p>
14
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<p>Rank these ester slowest to fastest for reactivity in hydrolysis</p>

Rank these ester slowest to fastest for reactivity in hydrolysis

  1. Benzyl Group

  2. 2 chain

  3. 1 Chain

  4. Formic acid

    1. More electron donating means slower hydrolysis

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