Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 13, Problem 41P
Interpretation Introduction
Interpretation:
The structure for the adduct formed in the reaction between
Concept introduction:
Diels-alder is a type of organic reaction in which substituted
The driving force of the reaction is the formation of new σ-bonds, which are energetically more stable than the π-bonds.
The general reaction of Diels-alder is as follows:
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Give the structure, exclusive of stereochemistry, of the principal organic product formed on reaction of 2,3-dimethyl-1,3-butadiene with each of the following:(a) 2 mol H2, platinum catalyst(b) 1 mol HCl (product of 1,2-addition)(c) 1 mol HCl (product of 1,4-addition)(d) 1 mol Br2 (product of 1,2-addition)(e) 1 mol Br2 (product of 1,4-addition)(f) 2 mol Br2
Account for the following :(a) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(b) Alkyl halides, though polar, are immiscible with water.(c) Grignard’s reagents should be prepared under anhydrous conditions.
(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.
(b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.
(i) Draw TWO (2) possible structures for compound B.
(ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.
(iii) Name the product formed when compound A undergoes bromination reaction.
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - Prob. 1PPCh. 13 - Prob. 2PPCh. 13 - Prob. 3PPCh. 13 - Practice Problem 13.4 From each set of resonance...Ch. 13 - Practice Problem 13.5 The following enol (an...Ch. 13 - Prob. 6PPCh. 13 - Practice Problem 13.7
Two compounds, A and B, have...Ch. 13 - Prob. 8PPCh. 13 - Prob. 9PPCh. 13 - Prob. 10PP
Ch. 13 - Prob. 11PPCh. 13 - Prob. 12PPCh. 13 - Prob. 13PPCh. 13 - Prob. 14PPCh. 13 - Prob. 15PPCh. 13 - Practice Problem 13.16
Diels–Alder reactions also...Ch. 13 - Prob. 17PPCh. 13 - Prob. 18PCh. 13 - What product would you expect from the following...Ch. 13 - Prob. 20PCh. 13 - Prob. 21PCh. 13 - Provide the reagents necessary for each of the...Ch. 13 - Prob. 23PCh. 13 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - When 1-pentene reacts with N-bromosuccinimide...Ch. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - 13.31 Provide a mechanism that explains formation...Ch. 13 - 13.32 Provide a mechanism that explains formation...Ch. 13 - Treating either 1-chloro-3-methyl-2-butene or...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Although both 1-bromobutane and 4-bromo-1-butene...Ch. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - 13.44 When furan and maleimide undergo a...Ch. 13 - Two controversial hard insecticides are aldrin and...Ch. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Prob. 48PCh. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Explain the product distribution below based on...Ch. 13 - Mixing furan (Problem 13.44) with maleic anhydride...Ch. 13 - Prob. 53PCh. 13 - Prob. 54PCh. 13 - Prob. 1LGPCh. 13 - Prob. 2LGP
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- (a) When bromine is added to two beakers, one containing phenyl iso propyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether? (b) Write any three methods in detail for the preparation of aldehyde from primary alcohol. (c) State the clemmenson reduction.arrow_forwardWhat will be the color of the flame and the amount of soot if the following are ignited:(a) Hexane (b)Heptane(c) Cyclohexane (d) Cyclohexene (e) Benzene (f) Toluenearrow_forwardWhat are the expected kinetic and thermodynamic products from addition of one mole of Br, to the following dienes? (b)arrow_forward
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- Give explanation of the correct option and explanation of the incorrect options.arrow_forward1. Write a structural formula for each of the following. (a) trans-3-methyl-3-hexene (c) 3,3-dimethylhexene (b) 1,5-hеxadiene (d) (Z)-2-hexene 2. Which of the following will decolorize the red-orange color of Br2/CH2C12 reagent? Ratienalise your answer. (a) ethenyl benzene (styrene) (b) methyl benzene (toluene) (c) hydroxyl benzene (phenol) (d) cyclohexanol 3. Draw the structure of the product(s) formed when Br/CH2C12 reacts with limonene (essential oil found in citrus rind). Br2 CH2CI2arrow_forward(a) How will you carry out the following conversions?(i) Acetylene to Acetic acid (ii) Toluene to m-nitrobenzoic acid(iii) Ethanol to Acetone(b) Give reasons :(i) Chloroacetic acid is stronger than acetic acid.(ii) pH of reaction should be carefully controlled while preparing ammonia derivatives of carbonyl compounds.arrow_forward
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