Question 1

Which of the following correctly assigns the formal charge to the oxygen atom in the structure $$\mathrm{HCO}$$, given that all atoms have complete octets and lone pairs are not shown?

Accepted Answer

$$-1$$

Question 2

Given the following pair of structures, which best describes their relationship?

$$\mathrm{CH_3CH_2OH}$$ and $$\mathrm{CH_3OCH_3}$$

Accepted Answer

Constitutional isomers

Question 3

Which of the following is the correct hybridization for the indicated carbon atom in piperine (the carbon in the double bond of the six-membered ring)?

Accepted Answer

$$sp^2$$

Question 4

In the tetracycline antibiotic shown, which functional group is circled at position A?

Accepted Answer

Ketone

Question 5

Which of the following best describes the resonance relationship between the two structures shown below?

$$\mathrm{O=C_6H_4=O}$$ $$\leftrightarrow$$ $$\mathrm{O^-}-C_6H_4=O^+$$

Accepted Answer

Resonance forms

Question 6

Which atom is the most basic in the following molecule?

$$\mathrm{NH_2CH_2COOH}$$

Accepted Answer

The nitrogen atom in $$\mathrm{NH_2$}$$

Question 7

Which hydrogen is the most acidic in acetic acid ($$\mathrm{CH_3COOH}$$)?

Accepted Answer

The hydrogen on the carboxyl group ($$\mathrm{COOH})$$

Question 8

For the equilibrium below, does the reaction favor the right or left side?

$$\mathrm{CH_3CH_2OH + OH^- \rightarrow CH_3CH_2O^- + H_2O}$$

Accepted Answer

Favors the left side ($$K_{eq} \u003c 1)$$

Question 9

Which of the following statements about resonance is correct?

Accepted Answer

Resonance forms represent different possible locations of electrons, not atoms.

Question 10

Which of the following is the correct Keq for the deprotonation of a compound with $$pK_a = 9 by $$sodium methoxide ($$pK_a of $$methanol $$\approx 16$$)?

Accepted Answer

$$K_{eq} \approx 10^7$

Question 11

Which functional group is present at position B in the tetracycline structure?

Accepted Answer

Amine

Question 12

What is the hybridization of the nitrogen atom in urobilin that is double-bonded to carbon?

Accepted Answer

$$sp^2$$

Question 13

Which of the following is a correct statement about constitutional isomers?

Accepted Answer

They have the same molecular formula but different connectivity.

Question 14

Which of the following is the most basic atom in methylamine ($$\mathrm{CH_3NH_2}$$)?

Accepted Answer

The nitrogen atom

Question 15

Which functional group is present at position C in the tetracycline structure?

Accepted Answer

Alcohol

Question 16

Which of the following best describes the relationship between $$\mathrm{CH_3CH_2NH_2}$$ and $$\mathrm{CH_3NHCH_3}$$?

Accepted Answer

Constitutional isomers

Question 17

Which atom is the most acidic in the following molecule?

$$\mathrm{CH_3COOH}$$

Accepted Answer

The hydrogen on the carboxyl group

Question 18

Which of the following is true about the equilibrium between $$\mathrm{C_6H_5NH_2}$$ and $$\mathrm{C_6H_5NH^-} in $$the presence of $$\mathrm{$$NaNH_2$$}$$?

Accepted Answer

Favors the right side ($$K_{eq} \u003e 1)$$

Question 19

Which of the following is a correct statement about hybridization?

Accepted Answer

A carbon atom in a double bond is $$sp^2$$ hybridized.

Question 20

Which of the following is the correct formal charge for the nitrogen atom in $$\mathrm{NH_4$^+}$$?

Accepted Answer

$$+1$$

Organic Chemistry I: Exam 1 Study Guide – Structure, Resonance, Acidity, and Functional Groups

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