Question 1

What is the correct IUPAC name for the compound shown below?

$$	ext{[See Image 1]}$$

Accepted Answer

2-hydroxybenzoic acid

Question 2

Which of the following is the correct IUPAC name for the compound shown below?

$$	ext{[See Image 2]}$$

Accepted Answer

3-hydroxyhexanoic acid

Question 3

What is the common name for the following compound?

$$\gamma-$$hydroxyvaleric acid

Accepted Answer

$$\gamma-$$hydroxyvaleric acid

Question 4

List the following weak acids in order of increasing acidity (from lowest to highest):

$$	ext{[See Image 3]}$$

Accepted Answer

4 \u003c 1 \u003c 3 \u003c 2 \u003c 5

Question 5

What compound is produced when $$(CH_3$)_2CHCH_2Br is $$subjected to the following sequence of steps?

1. $$Mg$$, $$Et_2O
2$$. $$CO_2
3$$. $$H_3O^+$$

Accepted Answer

3-methylbutanoic acid

Question 6

Which reagent sequence would convert benzene to benzoic acid?

Accepted Answer

1) $$Br_2$$, $$FeBr_3$$; 2) $$Mg$$; 3) $$CO_2$$; 4) $$H_3O^+$$, heat

Question 7

Which sequence of reagents would convert 1-hexene to hexanoic acid?

Accepted Answer

1) $$BH_3$$ \cdot THF$$; 2) H_2O_2$, HO$$^-$$; 3) Na_2Cr_2O_7$

Question 8

LiAl[OC$$(CH_3$)_3$$]$$_3H $$will reduce an acid chloride to which functional group?

Accepted Answer

Aldehyde

Question 9

Propose a reasonable synthetic route to prepare butanal from butanoic acid.

Accepted Answer

1) $$SOCl_2$$; 2) $$LiAlH[OC(CH_3$)_3]_3$$

Question 10

What is the major organic product when cyclopentene is treated with concentrated $$KMnO_4$$ and heat?

$$	ext{[See Image 4]}$$

Accepted Answer

$$CO_2$$ and glutaric acid (pentanedioic acid)

Question 11

Which of the following best explains why compound 5 in the acidity ranking (see Image 3) is the most acidic?

Accepted Answer

It has two electron-withdrawing chlorine atoms that stabilize the conjugate base.

Question 12

Which of the following is a correct statement about the reaction of a Grignard reagent with $$CO_2$$ followed by acid workup?

Accepted Answer

It produces a carboxylic acid with one more carbon than the original alkyl halide.

Question 13

Which of the following best describes the product of the oxidation of a primary alcohol with $$Na_2Cr_2O_7$$?

Accepted Answer

A carboxylic acid

Question 14

Which of the following is the correct order of increasing acidity for the compounds shown in Image 3?

Accepted Answer

4 \u003c 1 \u003c 3 \u003c 2 \u003c 5

Question 15

Which of the following reagents would NOT convert a primary alcohol to a carboxylic acid?

Accepted Answer

$$LiAlH_4$$

Organic Chemistry: Carboxylic Acids, Nomenclature, Acidity, and Reactions

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