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Chapter 13: Problem 47

Devise syntheses for the following molecules. You may use 1-butyne and ethyl iodide as your only sources of carbon, as well as any inorganic reagents you need.

Short Answer

Expert verified
1. Identify target and intermediates.2. Use 1-butyne and ethyl iodide to synthesize intermediates.3. Assemble into target molecule.

Step by step solution

01

Identify Target Molecule

Determine the structure of the target molecule you need to synthesize. Since it's not specified in the problem, choose any molecule suitable for synthesis using 1-butyne and ethyl iodide.
02

Break Down Target Molecule

Break down the structure of the target molecule into simpler components to identify potential intermediates.
03

Identify Key Reactions

Determine the key reactions needed to build the target molecule from the given starting materials (1-butyne and ethyl iodide).
04

Synthesize Intermediates

Use the given starting materials to synthesize the intermediates identified in the previous step.
05

Final Assembly

Combine the intermediates through the identified key reactions to form the target molecule.

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Key Concepts

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

target molecule identification
The first step in any organic synthesis problem is to identify the target molecule. This means recognizing the exact structure you need to synthesize. It's like having a final picture in a puzzle box before assembling the pieces. Start by examining the molecule's functional groups and carbon skeleton. For example, if you're asked to create a target molecule with an alcohol or ketone group, note this as it will guide your reaction choices. Clearly understanding the target will simplify subsequent steps.
reaction intermediate identification
After identifying the target molecule, break it down into simpler parts to determine possible intermediates. Think of these as stepping stones in the synthesis pathway. For example, if you're synthesizing a molecule with a double bond, you might break it down into two alkanes or an alkene and alkane. Make sure these intermediates are simpler and can be synthesized using available starting materials. Understanding the intermediates provides a roadmap for how you'll reach the final product.
key organic reactions
Now that you've identified the target molecule and potential intermediates, determine the key reactions required to synthesize these intermediates. This part is crucial as it involves selecting the right organic reactions. For example:
  • Alkylation: Adding a carbon chain to a molecule.
  • Hydrogenation: Adding hydrogen to convert double or triple bonds to single bonds.
  • Halogenation: Adding halogens like chlorine or bromine.
These reactions must be feasible with your starting materials, in this case, 1-butyne and ethyl iodide, and guide you toward the construction of the target molecule.
synthesis planning
Planning your synthesis is like drawing a map. Here’s how to do it:
  • Start with your target molecule and work backward, thinking of how you can form its structure from simpler components.
  • Decide the sequence of reactions that will help you assemble these components starting from your starting materials.
  • Consider reaction conditions and reagents available to you, ensuring they fit within the scope of the exercise.
By carefully planning, you'll be able to foresee potential problems and troubleshoot them in advance, making the synthesis pathway more efficient.
use of starting materials in synthesis
Finally, consider how to effectively use your starting materials, in this case, 1-butyne and ethyl iodide. Each starting material provides specific carbon frameworks and functional groups essential for synthesis:
  • 1-Butyne: Provides a three-carbon chain with a triple bond, useful for creating larger carbon skeletons and introducing branching points.
  • Ethyl Iodide: Contains a two-carbon chain and an iodine atom, making it very reactive for substitutions and additions.
Using these starting materials cleverly will allow you to build the intermediates and ultimately the target molecule efficiently.

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Most popular questions from this chapter

Unlike 2,3-pentadiene, 2,3,4-hexatriene exists as a pair of cis and trans isomers. Explain. Is \(2,3,4\)-hexatriene chiral or achiral?

Draw each of the following structures and indicate which are chiral and which are achiral: (a) 1,3 -dibromopropadiene, (b) 2 -methyl-2,3-pentadiene, (c) 1,3 -dichloro-1,2-butadiene, (d) 1,1 -dichloro-1,2-pentadiene.

In a fit of frustration or inspiration you decide to boil (reflux) your unanticipated \(\mathrm{C}_{10} \mathrm{H}_{12}\), and, in order to do that, you attach a long condenser to a receiving vessel that is kept very cold. Your \(\mathrm{C}_{10} \mathrm{H}_{12}\) boils at about \(165^{\circ} \mathrm{C}\), but you collect a product of the formula \(\mathrm{C}_{5} \mathrm{H}_{6}\) boiling at \(40^{\circ} \mathrm{C}\). Moreover, although this \(\mathrm{C}_{5} \mathrm{H}_{6}\) product is stable at low temperature for a long time, at room temperature it rapidly reverts to your starting \(\mathrm{C}_{10} \mathrm{H}_{12}\). Explain.

Predict the major product for the hydrohalogenation reaction (HBr, reflux, long time) with each of the following dienes: (a) 1,3 -butadiene (b) 1,3 -cyclopentadiene (c) \((Z)-1,3\)-pentadiene (d) \((E)-3\)-ethyl-1,3-pentadiene (e) 1 -methyl- 1,3 -cyclohexadiene

Life is never simple. There is a persuasive alternative argument that attributes the shortening of the butadiene \(\mathrm{C}(2)-\mathrm{C}(3)\) bond to factors other than conjugation. Can you come up with another explanation?
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