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Chapter 11: Problem 42

Devise syntheses for the following molecules starting from 3,3 -dimethyl-1-butene (1). You may use any inorganic reagent (no carbons) and the following "special" organic reagents: diazomethane, carbon tetrachloride, tertbutyl alcohol, tert-butyl iodide, \(\mathrm{Hg}(\mathrm{OAc})_{2}\), carbon, \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{~S}\), trifluoroperoxyacetic acid, strychnine, and Igor Likhotvoriks famous boiled goose-in-a-kettle. Your answers may be very short, and no mechanisms are required.

Short Answer

Expert verified
Identify functional groups, choose reagents, apply in sequence.

Step by step solution

01

Identify Functional Groups

Determine the functional groups present in the target molecule.
02

Recognize Reagents Capability

Understand the potential of each given reagent and how it can be used in the synthesis. For example, diazomethane can introduce a methyl group.
03

Plan Sequential Transformations

Design a pathway to transform 3,3-dimethyl-1-butene into the target molecule by breaking down the synthesis into smaller, manageable steps.
04

Apply Appropriate Reagents

Choose and apply the correct reagents in a logical sequence. For instance, if an alkoxy group needs to be added, use tert-butyl alcohol in presence of an appropriate catalyst.
05

Final Adjustments

Make any necessary adjustments to ensure the final product has the correct structure and functional groups.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Functional Group Identification
Identifying functional groups is crucial in organic synthesis. They determine how molecules react and interact. In this task, start by examining the target molecule. Look for groups such as alcohols, ethers, ketones, or esters. Compare them to the starting material, 3,3-dimethyl-1-butene. This molecule has an alkene functional group. Identifying the existing and target functional groups helps in planning a pathway.

Understanding the functional groups also helps in choosing the right reagents and reaction conditions. This first step is foundational for a successful synthesis.
Reagent Capabilities
Each reagent has specific capabilities guiding their application in synthesis. Knowing what each reagent can do narrows down the choices in each step of the synthesis.

For example:
  • Diazomethane can add a methyl group.
  • Carbon tetrachloride aids in chlorination reactions.
  • \textbf{Hg(OAc)\(_2\)} is used in oxymercuration reactions to add water across double bonds without rearrangement.
  • Trifluoroperoxyacetic acid is useful for oxidation.
      • Using sensitive reagents properly ensures that functional groups are introduced or manipulated effectively, making it essential to understand their potential.
Sequential Transformations
Designing a synthesis involves breaking down the transformation into manageable steps. Start with 3,3-dimethyl-1-butene and think about how to achieve the target molecule step by step.

Here’s a general approach:
  • Determine the transformations needed. E.g., adding a hydroxyl group requires an oxidation step.
  • For complex transformations, break them down into simpler reactions. Perform them in a logical sequence that avoids interfering with other functional groups.
  • Plan intermediate steps to gradually transform 3,3-dimethyl-1-butene. Ensure at each stage, the resulting compound is closer to the target molecule.
By carefully plotting sequential steps, you can achieve the desired transformations systematically and efficiently.
Appropriate Reagent Selection
Select reagents based on the transformations required. The compatibility of reagents with other functional groups in the molecule is important. A reagent effective in one scenario might not work well in another with different functional groups present.

For instance:
  • If adding an alcohol group, choose a reagent like \textbf{Hg(OAc)\(_2\)} with water for oxymercuration.
  • Avoid reagents that might cause unwanted side reactions.
  • If a specific functional group needs protection, use a suitable protecting group reagent.
      Choosing suitable reagents ensures each step proceeds smoothly without complications. Correct selection minimizes risks of side reactions or incompatibilities.
Target Molecule Adjustments
Sometimes, after all the planned steps, the molecule may still deviate slightly from the target. This final stage involves making necessary adjustments to fine-tune the molecule to the exact desired structure.

Common adjustments include:
  • Protecting group removal once the functional groups are in place.
  • Correcting stereochemistry to ensure the molecule has the correct 3D shape.
  • Making small alterations to functional groups if they are not perfectly placed.
      • These tweaks are essential for ensuring the final molecule matches the target structure, completing the synthesis accurately.

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Most popular questions from this chapter

Predict the major product(s), including stereochemistry where relevant, for the bromination reaction \(\left(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\right)\) with each of the following alkenes: (a) 1-pentene (b) cis-2-pentene (c) is-3-hexene (d) trans \(-3\)-hexene (e) \((R)-3\)-methyl-1-pentene

Show how you would make 3,3 -dibromohexane from ethyl bromide and acetylene. Assume you have access to any inorganic reagents.

Treatment of cis-2-butene with \(\mathrm{Br}_{2} / \mathrm{H}_{2} \mathrm{O}\) gives a product \(\mathrm{A}\left(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OBr}\right)\) that reacts with sodium hydride to give a meso compound \(\mathbf{B}\left(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\right)\). Compound \(\mathbf{B}\) has an \({ }^{1} H\) NMR spectrum \(8.05\) (1 H, quartet), \(1.30\) (3 H, doublet). With the same sequence of reagents, trans-2-butene gives a different compound \(\mathrm{C}\left(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OBr}\right)\), which gives compound D when treated with \(\mathrm{NaH}\) (a racemic mixture) of the same formula, \(\mathrm{C}_{4} \mathrm{H}_{\mathrm{s}} \mathrm{O}\). Compound \(\mathrm{D}\) has a \({ }^{1} \mathrm{H}\) NMR spectrum \(\delta 2.70(1 \mathrm{H}\), quartet \(), 1.30(3 \mathrm{H}\), doublet). Identify compounds A through D. Include stereochemical assignments in your answers.

Show how you would make trans-2methoxycyclohexanol starting with cyclohexene.

Devise syntheses for the following molecules starting from methylenecyclopentane (1). You may use any inorganic reagent (no carbons) and the following "special" organic reagents: dizzomethane, carbon tetrachloride, tert-butyl alcohol, methyl alcohol, ethyl alcohol, tert-butyl iodide, Hg \((\mathrm{OAc})_{2}\), carbon, \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{~S}\), trifluoroperacetic acid, and the secret contents of Zhou Enhai's favorite veggie dumplings. Your answers may be very short (one to three steps), and no mechanisms are required.
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