QUESTION 8 An alternative way to prepare aspirin (an ester) is to react acetic acid (a carboxylic acid) with salicylic acid (an alcohol), in the presence of H 3PO 4. This reaction is shown at the top of the diagram below. In addition to aspirin, water forms as a product. The water is formed from the portions of the reactant molecules that are enclosed in the box in the diagram. One of the aspects of organic chemistry that makes it incredibly useful is the fact that the reactions characteristic of each functional group will happen with ANY molecule that contains that functional group! ANY carboxylic acid can react with ANY alcohol (in the presence of an inorganic acid like H 3PO 4) to yield an ester. Ethyl butyrate is an ester that has the odor of pineapples (it is often used as "artificial" pineapple flavoring in candy). It can be prepared by reacting a carboxylic acid with an alcohol in the presence of acid. What is the structure of the carboxylic acid that must be involved in the synthesis of ethyl butyrate? H₂C carboxylic acid ??? FOH + HO (Question 8) CH3CH₂CH₂ OH HO CH3CH₂ OH CH3CH₂OH CH3CH₂CH₂OH H alcohol ??? (Question 9) H H₂PO4 acid HO O=C CH3 H ester H C-H + H₂O CH3CH₂CH₂ OCH₂CH3 Ethyl butyrate (pineapple odor)

Chemistry for Engineering Students
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Chapter4: Stoichiometry
Section: Chapter Questions
Problem 4.83PAE
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QUESTION 8
An alternative way to prepare aspirin (an ester) is to react acetic acid (a carboxylic acid) with salicylic acid (an alcohol), in the presence of H
3PO 4. This reaction is shown at the top of the diagram below. In addition to aspirin, water forms as a product. The water is formed
from the portions of the reactant molecules that are enclosed in the box in the diagram.
One of the aspects of organic chemistry that makes it incredibly useful is the fact that the reactions characteristic of each functional
group will happen with ANY molecule that contains that functional group! ANY carboxylic acid can react with ANY alcohol (in the
presence of an inorganic acid like H 3PO 4) to yield an ester.
Ethyl butyrate is an ester that has the odor of pineapples (it is often used as "artificial" pineapple flavoring in candy). It can be prepared
by reacting a carboxylic acid with an alcohol in the presence of acid.
What is the structure of the carboxylic acid that must be involved in the synthesis of ethyl butyrate?
H3C
FOH + HO
carboxylic acid
???
(Question 8)
CH3CH₂CH₂ OH
CH3CH₂ OH
CH3CH₂OH
+
CH3CH₂CH₂OH
HO
c=
alcohol
???
(Question 9)
H₂PO4
acid
но
O=C
CH3 H
ester
ܘ
—H +
CH3CH₂CH₂ OCH₂CH3
Ethyl butyrate
(pineapple odor)
H₂O
Transcribed Image Text:QUESTION 8 An alternative way to prepare aspirin (an ester) is to react acetic acid (a carboxylic acid) with salicylic acid (an alcohol), in the presence of H 3PO 4. This reaction is shown at the top of the diagram below. In addition to aspirin, water forms as a product. The water is formed from the portions of the reactant molecules that are enclosed in the box in the diagram. One of the aspects of organic chemistry that makes it incredibly useful is the fact that the reactions characteristic of each functional group will happen with ANY molecule that contains that functional group! ANY carboxylic acid can react with ANY alcohol (in the presence of an inorganic acid like H 3PO 4) to yield an ester. Ethyl butyrate is an ester that has the odor of pineapples (it is often used as "artificial" pineapple flavoring in candy). It can be prepared by reacting a carboxylic acid with an alcohol in the presence of acid. What is the structure of the carboxylic acid that must be involved in the synthesis of ethyl butyrate? H3C FOH + HO carboxylic acid ??? (Question 8) CH3CH₂CH₂ OH CH3CH₂ OH CH3CH₂OH + CH3CH₂CH₂OH HO c= alcohol ??? (Question 9) H₂PO4 acid но O=C CH3 H ester ܘ —H + CH3CH₂CH₂ OCH₂CH3 Ethyl butyrate (pineapple odor) H₂O
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