Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Question
Chapter 15.12C, Problem 15.20P
(a)
Interpretation Introduction
Interpretation:
The
Concept introduction:
When ultraviolet light is used rather than heat for
(b)
Interpretation Introduction
Interpretation:
The reaction of thermally allowed cycloaddition of two butadiene molecules is to be shown and an explanation corresponding to the fact that it is thermally allowed is to be stated.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
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6.) For the following reactions, please draw the structures of both the diene and dienophile that
would afford the depicted Diels Alder adducts.
1.
Cl
?
?
cl
Diene
Dienophile
cl
Cl
2.
CH3 O
CH3
?
CH3
Diene
Dienophile
CH3
3.
? + ?
Diene
Dienophile
4.
CH3
?
+
Diene
Dienophile
CH3
a. Show that [4+4] cycloaddition of two butadiene molecules to give cycloocta-1,5-diene is thermally forbidden but photochemically allowed
b.Thermally allowed cycloaddition of the two butadiene molecules when there's a different. Show reaction and explain why it is thermally allow
How many linear dienes have molecular formula C6H10? (Disregard cis–trans isomers.)
A. How many of the linear dienes in part a are conjugated dienes?
B. How many are isolated dienes?
C. How many are cumulated dienes?
Chapter 15 Solutions
Organic Chemistry (9th Edition)
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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- 3. Choose the answer that satisfy each statement. a. Under thermal conditions, (2E,4Z)-hexadiene undergoes a ring closure to form b. Under photochemical conditions, (2E,4Z)-hexadiene undergoes a ring closure to form A) conrotatory, cis-3,4-dimethylcyclobutene B) conrotatory, trans-3,4-dimethylcyclobutene C) disrotatory, cis-3,4-dimethylcyclobutene D) disrotatory, trans-3,4-dimethylcyclobutenearrow_forward6.) For the following reactions, please draw the structures of both the diene and dienophile that would afford the depicted Diels Alder adducts. 1. Diene Dienophile 2. CH3 O CH3 CH3 Diene Dienophile CH3 3. Diene Dienophile 4. CH3 Diene Dienophile CH3 4arrow_forward6.) For the following reactions, please draw the structures of both the diene and dienophile that would afford the depicted Diels Alder adducts. 1. ? + ? Diene Dienophile CH3 O CH3 ? + ? CH3 Diene Dienophile CH ? + ? Diene Dienophile ? + ? Dienophile Diene CHaarrow_forward
- 6. Answer ALL parts of this question: a) Draw all the molecular orbitals of ethene and buta-1,3-diene, indicating where applicable which are the HOMOS and which are the LUMOS in both the ground state and first excited state. b) Use relevant orbitals from those drawn above to explain why buta-1,3- diene reacts with ethene in a [4+2] cycloaddition reaction under thermal conditions, but if two molecules of ethene are to dimerise in a [2+2] cycloaddition reaction, then the reaction must be irradiated with ultraviolet light. c) Identify compound X in the following reaction (Scheme 4) and draw curly arrow mechanisms that lead to it and then lead from it to the final products. CO, Me .CO, Me heat heat CO,Me СО Ме Scheme 4 d) The reaction shown below (Scheme 5) is another example of a cycloaddition reaction. Identify the number of electrons involved in it, draw a curly arrow mechanism leading to the product and suggest whether this reaction would take place under thermal or photochemical…arrow_forwardThe diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: DA. The compound is not a conjugated diene. OB. This compound cannot adopt the s-cis conformation. C. The compound is lacking in electron donating groups. ⒸD. The compound is lacking in electron withdrawing groups.arrow_forward6. Answer ALL parts of this question: a) Draw all the molecular orbitals of ethene and buta-1,3-diene, indicating where applicable which are the HOMOS and which are the LUMOS in both the ground state and first excited state. b) Use relevant orbitals from those drawn above to explain why buta-1,3- diene reacts with ethene in a [4+2] cycloaddition reaction under thermal conditions, but if two molecules of ethene are to dimerise in a [2+2] cycloaddition reaction, then the reaction must be irradiated with ultraviolet light. c) Identify compound X in the following reaction (Scheme 4) and draw curly arrow mechanisms that lead to it and then lead from it to the final products. CO Me CO₂Me heat heat X CO₂Me CO Me Scheme 4 d) The reaction shown below (Scheme 5) is another example of a cycloaddition reaction. Identify the number of electrons involved in it, draw a curly arrow mechanism leading to the product and suggest whether this reaction would take place under thermal or photochemical…arrow_forward
- Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown CH3CH2O. Diene + Dienophile Co,CH3 •Consider E Z stereochemistry of alkenes. •Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the sign from the drop-down menu. C. P. opy aste %3Darrow_forwardThe diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: OA. The compound is lacking in electron withdrawing groups. B. The compound is not a conjugated diene. O C. The compound is lacking in electron donating groups. OD. This compound cannot adopt the s-cis conformation.arrow_forward1. Consider the Diels-Alder cycloaddition reaction below. D heat H D = deuterium = 2H Draw the major regioisomer (or in other words, constitutional isomer) expected to form. Draw appropriate resonance structures and explain why only one constitutional isomer is expected to form. Discuss if this can be drawn with both groups on the dieneophile being endo or one has to be endo and the other has to be exo.arrow_forward
- Explain why heating buta-1,3-diene forms 4-vinylcyclohexene but not cycloocta-1,5-diene.arrow_forward5. Predict the major product in the following Diels-Alder reaction using both the Valence Bond approach and the Molecular orbital theory. ۲۰ Final Productarrow_forwardDraw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Diene + Dienophile ? CH3 Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate multiple products using the + sign from the drop-down menu. Lits O. Sn [F CH3arrow_forward
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