Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
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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Students have asked these similar questions
Draw the structure consistent with each description.
a.(2E,4E)-octa-2,4-diene in the s-trans conformation
b.(3E,5Z)-nona-3,5-diene in the s-cis conformation
c.(3Z,5Z)-4,5-dimethyldeca-3,5-diene. Draw both the s-cis and s-trans conformations.
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-dimethylcyclobutene
6.) 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
CHa
Chapter 15 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global 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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Similar questions
- The 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_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_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
- 4. Give the structure of a conjugated diene with the molecular formula of C7H12.arrow_forwardDraw the structure of each compound.a. (Z)-penta-1,3-diene in the s-trans conformationb. (2E,4Z)-1-bromo-3-methylhexa-2,4-dienec. (2E,4E,6E)-octa-2,4,6-triened. (2E,4E)-3-methylhexa-2,4-diene in the s-cis conformationarrow_forward7. Although the Diels-Alder reaction generally occurs between an electron-rich diene and an electron- deficient dienophile, it is also possible to have inverse-demand Diels-Alder reactions between suitable electron-deficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels-Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regio-isomer is possible, draw both. la) CI CI Cl CH2 CI (b) H2C (c) H2C CO2CH3 H2C OCH3 - nth of maximumarrow_forward
- 7. Please choose the two reagents below that you would use to synthesize molecule X via a Diels-Alder reaction. Molecule X Which one of the following carbocations is the most stable? (Stability of carbocations) Which one of the following molecules is an example of a conjugated diene? Which one of the following dienes would you expect to be the most stable conjugated system (diene)? . What is the correct name for the following molecule? (An aromatic structure will be given. You have to know how to assign the carbon numbering and common names for aromatic compounds) A) 3-Fluoroaniline B) 3-Fluoroanisole C) 3-Fluroacetophenone D) 3-Fluorotoluene วarrow_forwardShow that the [4 + 4] cycloaddition of two butadiene molecules to give cycloocta1,5-diene is thermally forbidden but photochemically allowedarrow_forward5) A diene is a compound that contains two double bonds. When 1,3-cyclohexadiene reacts with DBr (analogous to HBr) the following is observed. Br DBr major product not formed a) Using words and structures, explain this distribution of products. b) Another product is formed in this reaction (shown below). Write a mechanism (with proper curved arrows) to explain its formation. D Brarrow_forward
- The diene shown below will NOT react in a Diels-Alder reaction. Why not? Select one: A. The compound is not a conjugated diene. B. The compound is lacking in electron withdrawing groups. O C. This compound cannot adopt the s-cis conformation. D. The compound is lacking in electron donating groups.arrow_forward[Review Topics] [References] Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. Diene + Dienophile CH3O CH₂ I wwwwwwwarrow_forward1. Rank the following dienes in order of increasing stability: a. trans-1,3-pentadiene, b. cis-1,3-pentadiene, c. 1,4-pentadiene, d. 1,2-pentadiene. 2) Show how the carbon p orbitals overlap to form the lowest energy л molecular orbital of 1,3- butadiene. 3) Draw the most stable conformation of (2Z, 4E)-2,4-hexadiene. 4) How many nodes, other than the node coincident with the molecular plane, are found in the highest energy л MO of 1,3-butadiene? 5) Give a representation of the highest occupied л MO of 1,3-butadiene in its ground state 6) Give a representation of the lowest occupied л MO of 1,3-butadiene in its ground state.arrow_forward
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