Question 1

Which of the following Lewis structures correctly represents N$$_2O$$, including all lone pairs and formal charges?

Accepted Answer

B) Structure B

Question 2

Which molecule below contains all three functional groups: ester, amine, and ketone?

Accepted Answer

B) Structure B

Question 3

Which line-angle structure corresponds to the condensed formula $$(\mathrm{CH}_3)_2\mathrm{CHO}(\mathrm{CH}_2)_3\mathrm{C}(\mathrm{CH}_3)_3$$?

Accepted Answer

D) Structure D

Question 4

Which of the following resonance structures is the major contributor for the given molecule?

Accepted Answer

A) Structure A

Question 5

Which line-angle structure correctly depicts the molecule as shown in the Newman projection?

Accepted Answer

C) Structure C

Question 6

Given the following reaction and p$$K_a$$ values:

$$\mathrm{H_2CO_3} + X \rightleftharpoons \mathrm{$$HCO_3$$^-} + \mathrm{PhSH}

p$K_a(H$_2CO$_3) = 6.5$$, p$$K_a($$PhSH) = 8.0. Which statement is correct?

Accepted Answer

C) The equilibrium lies to the left and X has a p$$K_b$$ value of 7.5

Question 7

Which of the following mechanisms correctly shows the flow of electrons and the roles of nucleophile (Nu) and electrophile (E) for the reaction of ethylamine with ethylene oxide?

Accepted Answer

A) Mechanism A

Question 8

Which of the following pairs of molecules are constitutional (structural) isomers?

Accepted Answer

A) The two molecules shown

Question 9

Which of the following compounds has the greatest molecular dipole moment?

Accepted Answer

D) NH$$_3$$

Question 10

Which compound displays the second-lowest p$$K_a$$ value?

Accepted Answer

A) H$$_2S$$

Question 11

What is the IUPAC name for the following molecule (see image 11)?

Accepted Answer

B) 2-Ethyl-7-methyloctane

Question 12

What is the IUPAC name for the following molecule (see image 12)?

Accepted Answer

D) 5-(2-Methylbutyl)-4-ethyl-7-methylnonane

Question 13

Which of the following 3-methylpentane conformations (Newman projections) has the second-lowest energy?

Accepted Answer

B) Conformation B

Question 14

Which is the most stable conformation of trans-1-tert-butyl-3-ethylcyclohexane?

Accepted Answer

B) Conformation B

Question 15

Assuming tertiary and secondary hydrogens are 6 and 4 times more reactive than primary hydrogens under the conditions shown, which product will be formed in greatest yield in the chlorination of 2,3-dimethylbutane?

Accepted Answer

B) Product B

Question 16

What is the expected major product of the following reaction under the specified conditions (bromination of 2,3-dimethylbutane)?

Accepted Answer

B) Product B

Question 17

Identify the carbocation of highest energy among the following options.

Accepted Answer

C) Carbocation C

Question 18

Which of the following illustrations depicts the correct mechanism for the second propagation step of free-radical fluorination of propane resulting in the formation of 2-fluoropropane?

Accepted Answer

A) Mechanism A

Question 19

Which reaction-energy diagram best represents the free-radical mono-fluorination of propane resulting in the formation of 2-fluoropropane?

Accepted Answer

A) Diagram A

Organic Chemistry I Exam Study Guidance (Lewis Structures, Functional Groups, Newman Projections, Resonance, and More)

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