Question 1

Which of the following compounds with the molecular formula $$C_4H_{10}O$$ contains an O–H bond?

Accepted Answer

tert-Butanol

Question 2

Which compound with the formula $$C_4H_8O$$ contains a C=O bond?

Accepted Answer

2-Butanone

Question 3

Which of the following compounds can form hydrogen bonds with water?

Accepted Answer

Diethyl ether

Question 4

Given the structure of cyclopentanone, how many hydrogen atoms are present in the molecule?

Accepted Answer

10

Question 5

What is the hybridization of the oxygen atom in cyclopentanone?

Accepted Answer

$$sp^2$$

Question 6

For the molecule $$CH_3CH_2CHC\equiv CCH(CH_3$)_2$$, what is the hybridization of the carbon atom in the triple bond?

Accepted Answer

$$sp$$

Question 7

Which type of intermolecular interaction is expected for $$CH_3CH_2CHC\equiv CCH(CH_3$)_2$$?

Accepted Answer

London dispersion forces

Question 8

In the structure below, what is the formal charge on the nitrogen atom? (Assume valence electrons: H=1, C=4, N=5)

Accepted Answer

0

Question 9

How many electrons are involved in the resonance forms of the nitrite ion ($$NO_2$$^-$$)?

Accepted Answer

4 (from the two $$	ext{N–O}$$ bonds)

Question 10

Which resonance form is the largest contributor to the structure of the nitrite ion ($$NO_2$$^-$$)?

Accepted Answer

The one with negative formal charge on the more electronegative atom (oxygen)

Question 11

Given the p$$K_a$$ values: cyclohexanol ($$pK_a = 15.7) $$and phenol ($$pK_a = 10.0$$), which is the stronger acid?

Accepted Answer

Phenol

Question 12

In the reaction below, identify the acid on the left side:

$$\mathrm{C_6H_{11}ONa} + \mathrm{C_6H_5OH} \rightleftharpoons \mathrm{C_6H_{11}OH} + \mathrm{C_6H_5ONa}$$

Accepted Answer

$$\mathrm{C_6H_5OH}$$

Question 13

Which side of the equilibrium is favored in the reaction between cyclohexanol and phenol? (Given $$pK_a$$ values: cyclohexanol = 15.7, phenol = 10.0)

Accepted Answer

Reactants (phenol and cyclohexanolate)

Question 14

Which of the following best explains why phenol is a stronger acid than cyclohexanol?

Accepted Answer

The phenoxide ion is resonance stabilized

Question 15

Which of the following statements about resonance is correct?

Accepted Answer

The actual molecule is a hybrid of all valid resonance forms

Question 16

Which orbital overlap forms a $$\pi$$ bond in an alkene?

Accepted Answer

$$sp^2$$–$$sp^2$$ side-on overlap

Question 17

Which of the following best describes the geometry around the oxygen atom in an alcohol?

Accepted Answer

Bent (due to two lone pairs)

Question 18

Which of the following is a correct statement about formal charge?

Accepted Answer

Formal charge is calculated by subtracting the number of assigned electrons from the number of valence electrons

Question 19

Which of the following molecules can exhibit both London dispersion forces and hydrogen bonding?

Accepted Answer

Methanol ($$CH_3OH)$$

Question 20

Which of the following best explains why $$sp-$$hybridized carbons are more electronegative than $$sp^3-$$hybridized carbons?

Accepted Answer

They have more $$s$$ character

Organic Chemistry Exam 1 Study Guide: Molecular Structure, Bonding, Resonance, and Acidity

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