All right, guys. So these next few questions are cumulative retrosynthesis based on the past few chapters of reactions. So, you do need to still know those. And I've made them so that they do represent common types of synthesis. Okay? But I've also made them all a little bit harder than what I've seen on most tests. Okay? That's a good thing. What that means is that I'm giving you some hard stuff so that by the time you get to your exam, it doesn't feel that bad. You're like, "Oh, wow. I did harder things with Clutch. I did harder things with Johnny online." For all of these retrosynthesis that I give you, the synthetic cheat sheet is very helpful. So, you should be looking at it or referencing it when you're stuck thinking, "Okay, are there any clues here? Are there any ways that I can get unstuck, that I can figure out where we're going?" Okay. So for all of these, I would really encourage you to try to do it on your own as best as you can. They're all doable. None of them are impossible. But they are tricky. They are hard. But they're doable. And then, of course, I'll answer it as always. Alright? So best of luck, guys. Let's go ahead and get started.
14. Synthetic Techniques
Retrosynthesis
14. Synthetic Techniques
Retrosynthesis - Video Tutorials & Practice Problems
The idea here is that we will be given a target molecule and the reactant and have to work backwards to fill in the missing pieces.
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concept
Intro
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Video transcript
As mentioned in the above video, some of these transformations may be harder than you need to know. Also, know that there are multiple ways to achieve one product but it is important to find the most effective and shortest way possible.
Time to put those skills to the test:)
2
Problem
ProblemSupply the reagents necessary to accomplish the following transformation.
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3
Problem
ProblemPropose a synthesis
A
B
C
D
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Problem
ProblemSupply the reagents necessary to accomplish the following transformation.
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Additional resources for Retrosynthesis
PRACTICE PROBLEMS AND ACTIVITIES (51)
- Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O...
- Show how you would convert the following starting materials into the target compound. You may use any addition...
- Using any necessary inorganic reagents, show how you would convert acetylene and isobutyl bromide to(b) (±)-2,...
- Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While ther...
- (•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or few...
- (•••) Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal nu...
- Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with ...
- Show how you would synthesize the following compounds.As starting materials, you may use any alcohols containi...
- Show how you would synthesize the following compound. As starting materials, you may use any alcohols containi...
- When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, ...
- (•••) Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with t...
- a. Propose a mechanism for the following reaction.2(CH3)2C=CH-CH3 + cat. H+--> 2,3,4,4-tetramethylhex-2-ene...
- Develop syntheses for the following compounds,using acetylene and compounds con-taining no more thanfour carbo...
- Develop syntheses for the following compounds,using acetylene and compounds con-taining no more thanfour carbo...
- Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than s...
- Propose mechanisms to explain the opposite regiochemistry observed in the following two reactions.<IMAGE>...
- Show how you would accomplish the following synthetic conversions.c. 2−methylcyclohexanol → 1−bromo−1−methylcy...
- Work backward to show how the cyclopropane would be synthesized from the chloroalkane shown.<IMAGE>
- For each of the following target molecules, design a multistep synthesis to show how it can be prepared from t...
- Identify A–E.<IMAGE>
- Using cyclooctyne as your starting material,show how you would synthesize the following compounds.(Once you ha...
- For each of the following target molecules, design a multistep synthesis to show how it can be prepared from t...
- A, a compound with molecular formula C6H10, contains three methylene units. A reacts with one equivalent of H2...
- Starting with cyclohexene, how can the following compounds be prepared? c. dicyclohexyl ether
- Fill in each box with the appropriate reagent: c.
- a. Starting with 3-methyl-1-butyne, how can you prepare the following alcohols? 2. 3-methyl-1-butanol b. In ...
- Write the appropriate reagent over each arrow.
- Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you ...
- Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you ...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (d) < of re...
- Complete each synthesis by providing the structure of the major product at each step, including any important ...
- Complete each synthesis by providing the structure of the major product at each step, including any important ...
- Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than s...
- Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways. (a)
- Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways. (b)
- Give the structures of the products represented by letters in this synthesis. Part 2:
- Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols co...
- Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols co...
- Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:...
- Give the structures of the intermediates represented by letters in this synthesis.<IMAGE of reactions>
- Give the structures of the products represented by letters in this synthesis. Part 1:
- Show how you would synthesize the following compounds. As starting materials, you may use any alcohols contai...
- Determine the structures of compounds A through G, including stereochemistry where appropriate.
- (•••) Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with t...
- Starting from bromobenzene and any other reagents and solvents you need, show how you would synthesize the fol...
- Show how you would use Grignard syntheses to prepare the following alcohol from the indicated starting materia...
- Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:...
- How could the following compounds be prepared, using cyclohexene as a starting material?a. <IMAGE>
- Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing c...
- b. Which of the reactions cannot be used for the synthesis of isobutyl alcohol?<IMAGE>
- For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reacta...