Question 1

Which of the following statements about bond-line structures is CORRECT?

Accepted Answer

Heteroatoms and hydrogens attached to heteroatoms must be shown explicitly.

Question 2

Given the condensed structure $\mathrm{CH_3CH_2OCH_2C(CH_3)_3}$, which is the correct bond-line structure?

Accepted Answer

A zigzag chain with an oxygen atom branching off the second carbon and a tert-butyl group at the end.

Question 3

Which functional group is present in the following structure: $\mathrm{R-COOR'}$?

Accepted Answer

Ester

Question 4

A neutral carbon atom typically forms how many bonds and has how many lone pairs?

Accepted Answer

$4$ bonds, $0$ lone pairs

Question 5

Which of the following is TRUE regarding resonance structures?

Accepted Answer

The resonance hybrid is an average of all significant resonance contributors.

Question 6

Which rule must be followed when drawing curved arrows for resonance?

Accepted Answer

Curved arrows should never break a single bond.

Question 7

What is the correct bonding pattern for a negatively charged oxygen atom?

Accepted Answer

$1$ bond and $3$ lone pairs

Question 8

Which of the following resonance contributors is the most significant?

Accepted Answer

The structure with the greatest number of filled octets.

Question 9

In a bond-line structure, what does each vertex (corner) represent?

Accepted Answer

A carbon atom

Question 10

Which of the following is NOT a general pattern for resonance?

Accepted Answer

A pi bond between two atoms of the same electronegativity

Question 11

Which of the following statements about delocalized electrons is CORRECT?

Accepted Answer

Delocalized electrons increase molecular stability by spreading charge.

Question 12

A positively charged carbon atom (carbocation) has:

Accepted Answer

$3$ bonds and $0$ lone pairs

Question 13

Which of the following is the correct order of significance for resonance structures, from most to least significant?

Accepted Answer

Structure with filled octets > Structure with fewer formal charges > Structure with negative charge on more electronegative atom

Question 14

Which of the following is TRUE about the use of dashed and solid wedges in three-dimensional bond-line structures?

Accepted Answer

Solid wedges show groups pointing out of the paper.

Question 15

Which of the following condensed structures corresponds to the Lewis structure of 2-bromopentane?

Accepted Answer

$\mathrm{CH_3CHBrCH_2CH_2CH_3}$

Question 16

Which of the following is a correct statement about functional groups?

Accepted Answer

Functional groups behave in a predictable way in every molecule where they occur.

Question 17

Which of the following is the correct formula for calculating formal charge?

Accepted Answer

$	ext{Formal Charge} = 	ext{Valence} - 	ext{lines} - 	ext{dots}$

Question 18

Which of the following is NOT a valid resonance pattern?

Accepted Answer

A sigma bond between two atoms with different electronegativities

Question 19

Which of the following statements about resonance hybrids is CORRECT?

Accepted Answer

The resonance hybrid is a blend of all significant resonance contributors.

Chapter 2: Molecular Representations and Resonance in Organic Chemistry

Study Guide - Practice Questions