
Interpretation: The diene and the dienophile that might be used to prepare the given racemic Diels-Alder adduct have to be found.
Concept Introduction:
Diels-Alder reaction:
It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a
Example:
Diels-Alder reaction to form bicyclic system:
The Diels-Alder adduct formed in the Diels-Alder reaction can also be a bicyclic system which will be obtained when cylopentadiene is used as the diene as shown here:
In this reaction, the cylopentadiene acts as both diene and dienophile and formed a bicyclic system. When it is heated to
Racemic mixture in Diels-alder reaction:
In the Diels-alder reaction, the formation of two new sigma bonds results in the formation of two new chiral centres that are enantiomers to each other. So, the Diels-alder adduct is the mixture of two enantiomers and therefore it is being a racemic Diels-alder adduct.

Trending nowThis is a popular solution!

Chapter 20 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Protecting Groups and Carbonyls 6) The synthesis generates allethrolone that exhibits high insect toxicity but low mammalian toxicity. They are used in pet shampoo, human lice shampoo, and industrial sprays for insects and mosquitos. Propose detailed mechanistic steps to generate the allethrolone label the different types of reagents (Grignard, acid/base protonation, acid/base deprotonation, reduction, oxidation, witting, aldol condensation, Robinson annulation, etc.) III + VI HS HS H+ CH,CH,Li III I II IV CI + P(Ph)3 V ༼ Hint: no strong base added VI S VII IX HO VIII -MgBr HgCl2,HgO HO. isomerization aqeuous solution H,SO, ༽༽༤༽༽ X MeOH Hint: enhances selectivity for reaction at the S X ☑arrow_forwardDraw the complete mechanism for the acid-catalyzed hydration of this alkene. esc 田 Explanation Check 1 888 Q A slock Add/Remove step Q F4 F5 F6 A བྲA F7 $ % 5 @ 4 2 3 & 6 87 Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Ce W E R T Y U S D LL G H IK DD 요 F8 F9 F10 F1 * ( 8 9 0 O P J K L Z X C V B N M H He commandarrow_forwardExplanation Check F1 H₂O H₂ Pd 1) MCPBA 2) H3O+ 1) Hg(OAc)2, H₂O 2) NaBH4 OH CI OH OH OH hydration halohydrin formation addition halogenation hydrogenation inhalation hydrogenation hydration ☐ halohydrin formation addition halogenation formation chelation hydrogenation halohydrin formation substitution hydration halogenation addition Ohalohydrin formation subtraction halogenation addition hydrogenation hydration F2 80 F3 σ F4 F5 F6 1 ! 2 # 3 $ 4 % 05 Q W & Å © 2025 McGraw Hill LLC. All Rights Reserved. F7 F8 ( 6 7 8 9 LU E R T Y U A F9arrow_forward
- Show the mechanism steps to obtain the lowerenergy intermediate: *see imagearrow_forwardSoap is made by the previous reaction *see image. The main difference between one soap and another soap isthe length (number of carbons) of the carboxylic acid. However, if a soap irritates your skin, they mostlikely used too much lye.Detergents have the same chemical structure as soaps except for the functional group. Detergentshave sulfate (R-SO4H) and phosphate (R-PO4H2) functional groups. Draw the above carboxylic acidcarbon chain but as the two variants of detergents. *see imagearrow_forwardWhat are the reactions or reagents used? *see imagearrow_forward
- The two pKa values of oxalic acid are 1.25 and 3.81. Why are they not the same value? Show the protontransfer as part of your explanation. *see imagearrow_forwardасть Identify all the bonds that gauche interact with C-OMe in the most stable conformation of the above compound.arrow_forwardPredict the reactants used in the formation of the following compounds using Acid-Catalyzed dehydration reactionarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

