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Chapter 11: Problem 11

Draw structural formulas for these compounds. (a) 2-(1-Methylethoxy) propane (b) trans-2,3-Diethyloxirane (c) trans-2-Ethoxycyclopentanol (d) Ethenyloxyethene (e) Cyclohexene oxide (f) 3-Cyclopropyloxy-1-propene (g) \((R)\)-2-Methyloxirane (h) 1,1-Dimethoxycyclohexane

Short Answer

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Question: Draw the structural formulas for the following compounds: (a) 2-(1-Methylethoxy) propane, (b) trans-2,3-Diethyloxirane, (c) trans-2-Ethoxycyclopentanol, (d) Ethenyloxyethene, (e) Cyclohexene oxide, (f) 3-Cyclopropyloxy-1-propene, (g) (R)-2-Methyloxirane, and (h) 1,1-Dimethoxycyclohexane. Answer: (a) CH3CH(OCH2CH3)CH3, (b) CH2OCH(CH3)CH(CH3), (c) C1(OH)C2(OCH2CH3)C3-C4-C5-C1, (d) CH2=CH-O-CH=CH2, (e) C1=C2C3C4C5C6OC1, (f) CH2=CHCH2(O-C3-ring), (g) CH2OCH(CH3)H, and (h) C1(OCH3)(OCH3)C2-C3-C4-C5-C6-C1.

Step by step solution

01

(a) 2-(1-Methylethoxy) propane

First, draw a propane chain (3 carbons) and then add an ethoxy group (OCH2CH3) at the second carbon. Replace one hydrogen at the first carbon of the ethoxy group with a methyl group (CH3). The structural formula should look like this: CH3CH(OCH2CH3)CH3.
02

(b) trans-2,3-Diethyloxirane

Draw an oxirane ring (a three-membered ring with one oxygen and two carbons). Place an ethyl group (CH2CH3) on both the second and third carbons, with both ethyl groups on opposite sides of the ring, indicating the "trans" configuration. The structural formula should look like this: CH2OCH(CH3)CH(CH3).
03

(c) trans-2-Ethoxycyclopentanol

Draw a cyclopentane ring (5 carbons) and add an ethoxy group (OCH2CH3) at the second carbon. At the first carbon, add a hydroxyl group (OH), making sure that the ethyl group is on the opposite side of the hydroxyl group on the ring, indicating the "trans" configuration. The structural formula should look like this: C1(OH)C2(OCH2CH3)C3-C4-C5-C1.
04

(d) Ethenyloxyethene

First, draw an ethene molecule (CH2=CH2) and connect an oxygen atom to one carbon of another ethene molecule (CH2=CH2). The structural formula should look like this: CH2=CH-O-CH=CH2.
05

(e) Cyclohexene oxide

Draw a cyclohexene ring (6 carbons, one of them being an alkene) and add an oxygen atom to the double bond. The structural formula should look like this: C1=C2C3C4C5C6OC1.
06

(f) 3-Cyclopropyloxy-1-propene

First, draw 1-propene (CH2=CHCH3) and add a cyclopropyl group (3 carbon ring) to the third carbon with an oxygen atom connecting them. The structural formula should look like this: CH2=CHCH2(O-C3-ring).
07

(g) \((R)\)-2-Methyloxirane

Draw an oxirane ring (a three-membered ring with one oxygen and two carbons). Place a methyl group (CH3) on the second carbon and assign it the(R)-configuration. This indicates that the priorities of atoms attached to the carbon follow a counter-clockwise direction, considering the lowest priority atom being out of the plane. The structural formula should look like this: CH2OCH(CH3)H.
08

(h) 1,1-Dimethoxycyclohexane

Draw a cyclohexane ring (6 carbons) and add two methoxy groups (OCH3) at the first carbon. The structural formula should look like this: C1(OCH3)(OCH3)C2-C3-C4-C5-C6-C1.

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Most popular questions from this chapter

Because of the Lewis base properties of ether oxygen atoms, crown ethers are excellent complexing agents for \(\mathrm{Na}^{+}, \mathrm{K}^{+}\), and \(\mathrm{NH}_{4}{ }^{+}\). What kind of molecule might serve as a complexing agent for \(\mathrm{Cl}^{-}\)or \(\mathrm{Br}^{-}\)?

Using your roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. Show all required reagents and all molecules synthesized along the way.

Using your roadmap as a guide, show how to convert 1-butene into dibutyl ether. You must use 1-butene as the source of all carbon atoms in the dibutyl ether. Show all required reagents and all molecules synthesized along the way.

The trimethylsilyl protecting group is easily removed in aqueous solution containing a trace of acid. Propose a mechanism for this reaction. (Note that a TBDMS protecting group is stable under these conditions because of the greater steric crowding around silicon created by the tbutyl group.)

Consider the possibilities for stereoisomerism in the bromohydrin and epoxide formed from trans-2-butene. (a) How many stereoisomers are possible for the bromohydrin? Which of the possible bromohydrin stereoisomers are formed by treating trans-2-butene with bromine in water? (b) How many stereoisomers are possible for the epoxide? Which of the possible stereoisomers is/are formed in this two-step sequence?
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