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Problem Set: Carboxylic Acids and Nitriles (CHE 311), Lecture notes of Chemistry

University of Mary (UMary)Chemistry

A problem set focused on carboxylic acids and nitriles for che 311. It includes various tasks such as ranking molecules in acidity, identifying reagents for transformations, and proposing synthesis routes for specific compounds. Students are expected to apply their knowledge of organic chemistry concepts to solve these problems.

What you will learn

  • Determine the structure of a compound based on its IR and 1H NMR spectra.
  • Propose a synthesis of Ibuprofen from benzene.
  • What is the order of acidity for the given molecules?
  • Which method is best for synthesizing carboxylic acids from alkyl halides?
  • Write the complete stepwise mechanism for the Fischer esterification reaction of methyl butanoate.
  • Which sequence of reagents will accomplish the transformation?

Typology: Lecture notes

2021/2022

Uploaded on 09/27/2022

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Problem Set 15_Carboxyli c Acids and Nitriles CHE 311
1. Rank the following molecules in acidity from most acidic to least acidic.
(1)
OH
O
A
OH
O
B
OH
OCl
Cl
Cl
C
(2)
OH
HO
OOCH3
OH
A B C D
(3)
COOH
NO2
COOH
OCH3
OH
NO2
OH
OCH3
ABC D
2. What sequence of reagents will accomplish the following transformation?
O
OH
pf3

Partial preview of the text

Download Problem Set: Carboxylic Acids and Nitriles (CHE 311) and more Lecture notes Chemistry in PDF only on Docsity!

1. Rank the following molecules in acidity from most acidic to least acidic.

OH

O

A

OH

O

B

OH

Cl O Cl Cl C

OH HO OH O (^) OCH 3 A B C D

COOH NO 2 COOH OCH 3 OH NO 2 OH OCH 3 A (^) B C D

2. What sequence of reagents will accomplish the following transformation?

O

OH

3. Methyl butanoate has been isolated from pineapple oil and can be prepared by the Fischer

esterification reaction shown below. Write the complete stepwise mechanism for this reaction.

Show all electron flow with arrows and include all intermediate structures.

4. Propose a synthesis of the anti-inflammatory drug Ibuprofen from benzene. Show all reagents

and all intermediate structures. Assume that ortho and para isomers can be separated.

(CH 3 ) 2 CHCH 2 CHCOOH

CH 3

Ibuprofen

+ + H 2 O

OCH 3

O

HCl CH 3 OH

OH

O