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(a)
Interpretation:
The product of the given Diels-Alder reaction is to be drawn along with the relative stereochemistry.
Concept introduction:
Diels-Alder reaction is a reaction between a conjugated diene and an
(b)
Interpretation:
The product of the given Diels-Alder reaction is to be drawn along with the relative stereochemistry.
Concept introduction:
Diels-Alder reaction is a reaction between a conjugated diene and an alkene. It is also known as
(c)
Interpretation:
The product of the given Diels-Alder reaction is to be drawn along with the relative stereochemistry.
Concept introduction:
Diels-Alder reaction is a reaction between conjugated diene and alkene It is known as
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Chapter 15 Solutions
Organic Chemistry
- (a) Discuss the aromaticity of a six membered heterocyclic compound which is weak base in nature. (b) Discuss about the stability factors of the reaction intermediates, which involved in a name reaction "Wittig rearrangement".arrow_forwardThe natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem Comm. 2014, 50, 13725) (a) Using three molar equivalents of BrCL please provide a mechanism to account for the formation of the bracketed structure (you do not need to show stereochemistry in this mechanism) HB (3 equiv) myrcene balomon 8.61a Add curved arrow(s) to show the mechanism steps. Edit Drawing sitsarrow_forward(a) Complete the following sequence of reactions (i.e., give the structure for compounds A and B), giving structural details of all key intermediates. heat & A COOCH3 H₁₂ Ni (b) Provide the bond line structures for the pair of compounds used for the Diels-Alder synthesis of the compound shown below. O B COOCH3 (c) Draw the two major products obtained when (3E,5Z)-2,2,3,6,7-pentamethylocta-3,5-diene reacts with HBr at low and high temperatures. Label the products as the kinetic or thermodynamic product AND, if applicable, use dashes and wedges to show the correct stereochemistry in the obtained products.arrow_forward
- Many variations of ring-closing metathesis have now been reported. Tandem ring–opening–ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon–carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.arrow_forwardFor each of the following, write the major product(s) and then draw out each step in the mechanism using curved arrows. Show ALL lone pair electrons and formal charges. Redraw ALL molecules as to show explicitly ALL bonds being broken or formed. Identify the molecular orbital (HOMO) of the nucleophile and the molecular orbital (LUMO) of electrophile involved in the nucleophilic attack. MO diagrams are not necessary. (a). (b). -CHO 2. H₂O 1. LiAlH4 2. H₂O MgBr , etherarrow_forwardMany variations of ring-closing metathesis have now been reported. Tandem ring-opening-ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon-carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.arrow_forward
- The central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other.(a) Draw an orbital diagram of allene, showing why the two ends are perpendicular.(b) Draw the two enantiomers of penta-2,3-diene. A model may be helpfularrow_forward(a) Which of the following phenols is the least acidic? (b) Which of the following phenols is the most acidic?arrow_forward(a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomericproducts are formed. Give their structures, and label each asymmetric carbon atomas (R) or (S). What is the relationship between these isomers?(b) Repeat part (a) for (E)-3-methylhex-3-ene. What is the relationship between the productsformed from (Z)-3-methylhex-3-ene and those formed from (E)-3-methylhex-3-ene?arrow_forward
- (A) Which triene has the smallest heat of hydrogenation? Explain why. (B) Which triene can be reactive in the Diels-Alder reaction? (C) Which triene is the most reactive in the Diels-Alder reaction?arrow_forward(a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). THF A Ph Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Method B is not preferred synthetic route due to the number of steps involve (3 steps vs 1 step for Method A). What else is making method A unfavorable synthetic method? Use curly arrows to explain this effect. (Ctrl) -arrow_forward(a) Why cyclohexene and cyclohexa-1,3-diene are expected to undergo addition reaction but benzene does not? Explain clearly. (b) Why is an electron-donating group to benzene activating and usually a/an ortho/para director?arrow_forward
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