Question 1

Name the carboxylic acid.

Accepted Answer

The longest chain containing the carboxylic acid is highlighted in red below. The name is 2,5-dimethylheptanoic acid.

Question 2

Provide structures for products A-D. The 1H NMR spectrum of D is given.
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Accepted Answer

Step 1 is chlorination of benzene. Step 2 is the Friedel-Crafts alkylation of chlorobenzene. Step 3 is the bromination of the benzyl protons to give a benzyl bromide. Step 4 converts the bromide to a Grignard reagent, then reacts with formaldehyde to give a primary alcohol.

Compound D matches the ¹H NMR spectra. The four protons >7ppm belong to the aromatic protons. The singlet is the hydroxy proton. The two triplets belong to the -CH₂CH₂- group.

Question 3

Which of the carboxylic acids would not decarboxylate (lose CO2) upon warming?

Accepted Answer

A)  compound A 
B)  compound B 
C)  compound C 
D)  compound D 
E)  neither compound C nor compound D would decarboxylate upon warming 
A)  compound A 
B)  compound B 
C)  compound C 
D)  compound D 
E)  neither compound C nor compound D would decarboxylate upon warming E

Question 4

Draw the structure of the nucleophile (including formal charges) that would give the product on the right.

Accepted Answer

A carboxylate ion re

Question 5

Outline a multistep synthesis of the transformation.

Accepted Answer

Working backward, you know a thioether c

Question 6

Draw the structure of the nucleophile (including formal charges) that would give the product on the right.

Accepted Answer

A carboxylate ion re

Question 7

Predict the major organic product for the reaction. If you believe no reaction would occur, write NR.

Accepted Answer

A Grignard reagent is very bas

Question 8

A student has synthesized two isomers, A and B, but neglected to label the flasks. Suggest a spectroscopy method the student could use to quickly differentiate between them and explain what feature they would be looking for.

Accepted Answer

The student is comparing a carboxylic ac

Question 9

Outline a multistep synthesis to perform the transformation.

Accepted Answer

Working backward, you've added a carbon

Question 10

Predict the major organic product for the reaction.

Accepted Answer

Lithium aluminum hydride (LiAlH₄) will re

Question 11

Rank the functional groups in order of highest priority to lowest for nomenclature.

Accepted Answer

A)  alcohol > aldehyde > carboxylic acid > thiol 
B)  aldehyde > carboxylic acid > thiol > alcohol 
C)  thiol > carboxylic acid > aldehyde > alcohol 
D)  carboxylic acid > aldehyde > alcohol > thiol 
A)  alcohol > aldehyde > carboxylic acid > thiol 
B)  aldehyde > carboxylic acid > thiol > alcohol 
C)  thiol > carboxylic acid > aldehyde > alcohol 
D)  carboxylic acid > aldehyde > alcohol > thiol

Question 12

Outline a multistep synthesis of the transformation.

Accepted Answer

Working backward, you've learned that es

Question 13

Which compound decarboxylates fastest?

Accepted Answer

A)  compound A 
B)  compound B 
C)  compound C 
D)  compound D 
E)  compound E 
A)  compound A 
B)  compound B 
C)  compound C 
D)  compound D 
E)  compound E

Question 14

Which statement is true of soaps?

Accepted Answer

A)  Soap is made by reduction of a fatty acid. 
B)  Soap is positively charged. 
C)  Soap has a long hydrocarbon tail and ionic head group. 
D)  Soap molecules form micelles, where the polar head groups are on the inside of the ball and the tails are on the outside. 
A)  Soap is made by reduction of a fatty acid. 
B)  Soap is positively charged. 
C)  Soap has a long hydrocarbon tail and ionic head group. 
D)  Soap molecules form micelles, where the polar head groups are on the inside of the ball and the tails are on the outside.

Question 15

Outline a one-step synthesis of the anhydride.

Accepted Answer

Anhydrides can be formed from

Question 16

Give the IUPAC and common name for the dicarboxylic acid.

Accepted Answer

The dicarboxylic aci

Question 17

Which side is favored at equilibrium?

Accepted Answer

A)  the left 
B)  the right 
C)  need to know pKa values of the individual acids before estimating 
D)  the equilibrium depends on the temperature of the measurement, and thus can't be known 
E)  neither, Keq = 1 
A)  the left 
B)  the right 
C)  need to know pKa values of the individual acids before estimating 
D)  the equilibrium depends on the temperature of the measurement, and thus can't be known 
E)  neither, Keq = 1