Question 1

Which of the following is the correct Lewis structure for the nitrate ion ($$\mathrm{NO_3$^-}$$), including all resonance forms and formal charges?

Accepted Answer

Three resonance structures, each with a double bond to a different oxygen, and a -1 formal charge on one oxygen in each structure.

Question 2

Classify the compound sodium benzoate ($$\mathrm{C_6H_5COONa}) as $$ionic, covalent, or a mixture of ionic and covalent bonds.

Accepted Answer

Mixture of ionic and covalent

Question 3

What is the molecular formula ($$\mathrm{C_xH_y}) of $$styrene, given its expanded structure?

Accepted Answer

$$\mathrm{C_8H_8}$$

Question 4

Determine the hybridization of all non-hydrogen atoms in acetamide ($$\mathrm{CH_3CONH_2}).$$

Accepted Answer

C (methyl): $$sp^3$$, C (carbonyl): $$sp^2$$, O: $$sp^2$$, N: $$sp^2$$

Question 5

Rank the following resonance structures of acetate ion from most to least important (stability):

Accepted Answer

Structures with delocalized negative charge on oxygen are most important.

Question 6

Which of the following lone pairs in the amide group ($$\mathrm{$$CONH_2$$}) is $$delocalized?

Accepted Answer

The lone pair on nitrogen is delocalized due to resonance with the carbonyl group.

Question 7

Label the functional groups and indicate 1°, 2°, or 3° for the following compound: $$\mathrm{CH_3CH(OH)CH_2NH_2}$$

Accepted Answer

Alcohol (2°), Amine (1°)

Question 8

Which of the following potential energy diagrams represents an exothermic reaction?

Accepted Answer

Diagram where products are lower in energy than reactants.

Question 9

Given the reaction coordinate diagram, which arrow represents the activation energy of the forward reaction?

Accepted Answer

Arrow from reactants to the peak of the curve.

Question 10

Which statement about carbocations is NOT true?

Accepted Answer

Carbocations are nucleophiles.

Question 11

Which of the following is the correct conjugate base of $$\mathrm{$$HSO_4$$^-}$$?

Accepted Answer

$$\mathrm{SO_4$^{2-}}$$

Question 12

Which of the following is the correct staggered conformation for rotation about the $$\mathrm{C_2$-C_1$}$$ bond in butane?

Accepted Answer

Conformation with methyl groups anti to each other.

Question 13

Which trimethylcyclohexane has the most stable chair conformation?

Accepted Answer

The one with all methyl groups in equatorial positions.

Question 14

For the following alkene, assign the configuration of the double bond as either E or Z: $$\mathrm{CH_3CH=$$CHCH_3$$}$$

Accepted Answer

E (trans)

Question 15

Rank the following alkenes in increasing order of stability: ethylene, cis-2-butene, trans-2-butene, 2-methyl-2-butene.

Accepted Answer

Ethylene \u003c cis-2-butene \u003c trans-2-butene \u003c 2-methyl-2-butene

Question 16

Which of the following best describes the reaction: $$\mathrm{R-OH + HBr \rightarrow R-Br + H_2O}$$?

Accepted Answer

Substitution reaction

Question 17

Which arrow in the reaction coordinate diagram represents the transition state?

Accepted Answer

The peak of the energy curve.

Question 18

Which of the following statements about bond dissociation energies is correct?

Accepted Answer

Bond dissociation energies decrease down a column of the periodic table.

Question 19

Which of the following is true about the activation energy ($$E_a) of a $$reaction?

Accepted Answer

$$E_a is $$the energy difference between reactants and the transition state.

Organic Chemistry Fundamentals: Structure, Bonding, and Reactivity Study Guide

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