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Chapter 17: Problem 366

Synthesize trans-1-methoxy-2-methylcyclopentane from 1-methylcyclopentene using any needed reagents.

Short Answer

Expert verified
Perform hydrogenation of 1-methylcyclopentene using a Pd/C catalyst and hydrogen gas, followed by an SN2 reaction with Methanol (CH3OH) and Hydrochloric acid (HCl) to obtain the desired trans-1-methoxy-2-methylcyclopentane. Confirm the final product using analytic methods such as NMR or IR spectroscopy.

Step by step solution

01

Understanding the Target Molecule

The target molecule is trans-1-methoxy-2-methylcyclopentane. The term "trans" refers to a geometric isomer where the two functional groups (in this case, the methoxy and methyl groups) are on opposite sides of the molecule. Understanding the structure of the target molecule is vital for deciding the reaction pathway.
02

Analyzing the Starting Molecule

Starting from 1-methylcyclopentene, it already has a methyl group attached. However, it lacks the methoxy group, and it is an alkene. This implies that the reaction to form the desired product would involve two main stages: the addition of a methoxy group and the removal of the double bond.
03

Carrying out the Reactions

The first step is breaking the double bond in the starting molecule. This can be achieved by performing hydrogenation using a catalyst like Pd/C and hydrogen gas, under pressure. This will convert the alkene into an alkane, ensuring there's no double bond, and hence setting the foundation for the SN2 reaction.
04

Adding the Methoxy Group

Now with the substrate ready, the next step is to introduce the methoxy group. For this, perform an SN2 reaction using Methanol (CH3OH) and an acid like Hydrochloric acid (HCl). The positive charge of the Hydrogen ion reacts with the Oxygen of the Methanol, creating a good leaving group, which can be replaced by the nucleophile, resulting in the desired trans-1-methoxy-2-methylcyclopentane. Each step should be followed by purification processes such as distillation or extraction to ensure removal of byproducts before proceeding to next reaction.
05

Confirming the Structure

Once the synthesis is complete, confirm the structure of the final product using analytic methods such as NMR or IR spectroscopy to ensure that it matches the desired trans-1-methoxy-2-methylcyclopentane molecule. Note: The reagents and conditions would favor the trans product owing to the SN2 mechanism, but it's essential to consider that the cis-isomer may also be formed and might need separation.

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Most popular questions from this chapter

In ether formation by dehydration, as in most other cases of nucleophilic substitution, there is a competing elimination reaction. What is this reaction and what products does it yield? For what alcohols would elimination be most important?

An alkyl bromide, \(\mathrm{C}_{5} \mathrm{H}_{11}\) Br reacted rapidly with water to give an alcohol \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\), but when the alkyl bromide was treated with sodium methoxide in an attempt to convert it to an ether, the only product was an alkene, \(\mathrm{C}_{5} \mathrm{H}_{10}\) Ozonolysis of this alkene gave two carbonyl compounds as products, a ketone \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\) and an aldehyde \(\mathrm{C}_{2} \mathrm{H}_{4} \mathrm{O} .\) What was the structure of the alkyl bromide?

A homogeneous solution is known to contain equal parts of diethyl ether and pentane. These liquids have similar boiling points and cannot be separated by fractional distillation. Devise a method for separating them.

Write a mechanism for the reaction of trans-2-butene with trifluoroperacetic acid which is consistent with the fact that the rate is first order in each participant and gives cis addition.

Name each of the following compounds: (a) \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\) (b) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2}\right)_{2}-\mathrm{O}\) (c) \(\left(\mathrm{CH}_{3}\right){ }_{2} \mathrm{CH}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{3}\) (e) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH}\) (f) CC(Cl)CC1CO1
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