Q: Which of the following compounds has the lowest boiling point? Consider the intermolecular forces present in each compound. $$\text{CH}_3\text{CH}_2\text{C(O)CH}_2\text{CH}_3$$ $$\text{CH}_3(\text{CH}_2)_4\text{CH}_3$$ $$\text{CH}_3(\text{CH}_2)_4\text{OH}$$ $$\text{CH}_3\text{CH}_2\text{CH}_2\text{OCH}_2\text{CH}_3$$

$$\text{CH}_3(\text{CH}_2)_4\text{CH}_3$$

Q: Which of the following is the correct condensed structural formula for benzyl butyl ether?

$$\text{C}_6\text{H}_5\text{CH}_2\text{OCH}_2\text{CH}_2\text{CH}_2\text{CH}_3$$

Q: Which of the following sequences correctly describes the synthesis of an ether from an alkyl halide and an alcohol?

Williamson ether synthesis: $$\text{R-X} + \text{R'}\text{OH} \rightarrow \text{R-O-R'} ($$using base)

Q: Which of the following is the correct sequence to convert hex-1-ene to 1-methoxyhexan-2-ol?

1. Hydroboration-oxidation ($$\text{BH}_3$$, $$\text{H}_2\text{O}_2) 2. $$Etherification with methanol

Q: Which carbon is considered allylic in the molecule $$\text{CH}_2=CHCH_2CH_3$$?

The $$\text{CH}_2$$ group adjacent to the double bond (third carbon)

Question 1

Which of the following compounds has the lowest boiling point? Consider the intermolecular forces present in each compound.

$$	ext{CH}_3	ext{CH}_2	ext{C(O)CH}_2	ext{CH}_3$$
$$	ext{CH}_3(	ext{CH}_2)_4	ext{CH}_3$$
$$	ext{CH}_3(	ext{CH}_2)_4	ext{OH}$$
$$	ext{CH}_3	ext{CH}_2	ext{CH}_2	ext{OCH}_2	ext{CH}_3$$

Accepted Answer

$$	ext{CH}_3(	ext{CH}_2)_4	ext{CH}_3$$

Question 2

Which of the following is the correct condensed structural formula for benzyl butyl ether?

Accepted Answer

$$	ext{C}_6	ext{H}_5	ext{CH}_2	ext{OCH}_2	ext{CH}_2	ext{CH}_2	ext{CH}_3$$

Question 3

What is the IUPAC name for $$(	ext{CH}_3)_2	ext{CHOCH}_2	ext{Cl}$$?

Accepted Answer

2-chloro-2-methoxypropane

Question 4

Which of the following sequences correctly describes the synthesis of an ether from an alkyl halide and an alcohol?

Accepted Answer

Williamson ether synthesis: $$	ext{R-X} + 	ext{R'}	ext{OH} ightarrow 	ext{R-O-R'} ($$using base)

Question 5

Predict the major product of the reaction: $$	ext{CH}_2=CHCH_2Br + 	ext{NaOH} ightarrow$$ ?

Accepted Answer

$$	ext{CH}_2=CHCH_2OH$$

Question 6

Which of the following is the correct sequence to convert hex-1-ene to 1-methoxyhexan-2-ol?

Accepted Answer

1. Hydroboration-oxidation ($$	ext{BH}_3$$, $$	ext{H}_2	ext{O}_2) 2. $$Etherification with methanol

Question 7

A compound with three double bonds in a row is best described as:

Accepted Answer

Cumulated

Question 8

Which carbon is considered allylic in the molecule $$	ext{CH}_2=CHCH_2CH_3$$?

Accepted Answer

The $$	ext{CH}_2$$ group adjacent to the double bond (third carbon)

Question 9

Which of the following best describes the resonance structures for the allyl cation ($$	ext{CH}_2=$$CHCH_2$$^+$$)?

Accepted Answer

The positive charge is delocalized over all three carbons

Question 10

In a Diels-Alder reaction, which diene would react faster: 1,3-butadiene or 2,3-dimethyl-1,3-butadiene? Explain based on electron density.

Accepted Answer

2,3-dimethyl-1,3-butadiene, because methyl groups increase electron density and reactivity

Question 11

Which of the following compounds is aromatic according to Huckel's rule?

Accepted Answer

Benzene

Question 12

Which nitrogen atom in pyridine is part of the aromatic system?

Accepted Answer

The nitrogen's $$sp^2$$ orbital participates in the aromatic system

Question 13

Which of the following ions is more stable: cyclopropyl cation or allyl cation? Justify your answer.

Accepted Answer

Allyl cation, due to resonance stabilization

Question 14

Which compound is more basic: aniline or 4-nitroaniline? Explain your reasoning.

Accepted Answer

Aniline, because the nitro group decreases basicity by withdrawing electrons

Question 15

What is the correct condensed structural formula for 2-phenylpropan-1-ol?

Accepted Answer

$$	ext{C}_6	ext{H}_5	ext{CH}_2	ext{CH(OH)CH}_3$$

Question 16

Which of the following best describes the mechanism for the formation of an ether via the Williamson ether synthesis?

Accepted Answer

SN2 attack of an alkoxide ion on an alkyl halide

Question 17

Which of the following is the correct name for the compound $$	ext{C}_6	ext{H}_5	ext{NH}_2$$?

Accepted Answer

Aniline

Question 18

Which of the following compounds is antiaromatic?

Accepted Answer

Cyclobutadiene

Question 19

Which of the following reactions is a classic example of a Diels-Alder reaction?

Accepted Answer

$$	ext{1,3-butadiene} + 	ext{maleic anhydride} ightarrow 	ext{cis-4,5-dicarboxylic cyclohexene}$$

Organic Chemistry Test 1 Study Guidance: Chapters 14–16

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