None Consider the following reaction between Diene A with one equivalent of D-Br, noting deuterium (anisotope of hydrogen) is present rather than hydrogen in the acid. Use the diene numbering schemeprovided as you draw your products.3.+ D-Br2Diene A1,2-product1,4-producta. (8) Draw the major products of this reaction in the spaces provided above.b. (2) Circle the kinetic product.c. (2) Underline the thermodynamic product.d. (2) T or F. The thermodynamic product is less stable than the kinetic product.e. (2) T or F. The kinetic product is formed more slowly than the thermodynamic product.f. (2) T or F. Low reaction temperatures favor the thermodynamic product.Draw the mechanism for the formation of the 1,4-product you drew in 3.a. above, ensuring youinclude all electron pairs, electron-pushing arrows and intermediates.

here the 1,4-addition product is more thermodynamically favorable over 1,2 addition product.At low…

Answered: Consider the following reaction between…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 36CTQ

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4.) For the following dienes A-G, please circle which organic molecules would not function as dienes in a Diels Alder reaction? H3C CH3 CH2 H3C H B CH3 H3C CH3 H2C CH2 H-CEC CH2 H3C F G 5.) For the following molecules V-Z, please circle which organic molecules would function well as dienophiles in a Diels Alder reaction. H3C CH3 CN N-CH3 H3C CH3 H3C-0 O-CH3 V. 3
3. Please rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction (i.e. 1 = fastest or most reactive diene, 4 = slowest or least reactive diene). Put your answer on the line below each structure. %3D OMe OMe OMe
1. In a Birch reaction, an aromatic compound can be treated with Na/CH3OH, it can also be treated with Li/NH3 and have the same product form. One of the intermediates in the Birch reaction is a radical anion. In the example below, anisole could possibly form a radical anion A or B, then will go into C and D. Li/NH3 A B C D A. With the knowledge you have gained from what we have discussed, which anion A or B is more stable? What is your reasoning? B. Is a Birch reaction and oxidation or reduction? Why?
6., Draw the diene and dienophile which would be used to prepare the following bicyclic compound. Label the diene and dienophile. A NO₂ H H NO₂
3. For each reaction, draw the structure(s) of the major product(s) from the addition of 1 equivalent of HX to the conjugated diene at a) 0 degrees C and b) 40 degrees C. Br + HBr → Br
Given the following reaction involving a diene and dienophile answer the following questions. A. Given the following reaction two products are formed, one major and one minor. Draw the two possible regiomeric products and indicate which is MAJOR. HO HH B. Draw resonance diagrams below to explain your choice for MAJOR product.
8. Circle the reactions that are synthetically useful (i.e.give only one major product). ~ Br₂, hv Cl₂, hv A NBS, hv NBS, hv
5. Write a detailed chemical mechanism for the following reaction. [10 pts] NBS hv ? For full credit, • Explicitly label initiation, propagation, and termination steps. • Use 'curly arrows' to denote electron flow. Show all resonance forms of the reaction intermediate(s). N-Br NBS (N-bromosuccinimde) • Show reaction at any resonance forms of the reaction intermediate(s) that lead to different products. including constitutional and stereochemical isomers (if any). Show two different termination steps. Showing more steps will not earn points; wrong steps will lose points
2. Please rank the following dienophiles in their rate of reaction with the same diene in a Diels-Alder reaction (i.e. 1= fastest or most reactive dienophile, 4 = slowest or least reactive dienophile). Put your answer on the line below each structure. 3. Please rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction (i.e. 1= fastest or most reactive diene, 4 = slowest or least reactive diene). Put your answer on the line below each structure. OMe OMe OMe |
2. The structures of alkenes can affect their reactivity in the reaction with H-Br. H;C H H;C H H H H `H H;C `H H `H A B (a) Arrange the reactivity of above alkenes (A, B and C) in an increasing order. AL (b) Use the carbocation formation to show the ease of alkenes to accept a proton from HBr.
#8).
5) 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 Br

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