Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 30.SE, Problem 33AP
Interpretation Introduction
Interpretation:
The stereochemistry, suprafacial or antarafacial, expected for the photochemical [1,5] sigmatropic rearrangement reaction is to be stated.
Concept introduction:
Sigmatropic rearrangements involve the migration of a σ bond present at the end or in the middle of the system across the π electron system from one position to another. They are represented by [m,n] where m and n represents the number of atoms between the bond being broken and the bond being formed in two directions.
If even number of electron pair is involved then thermal reaction occur through antarafacial pathway and photochemical reactions occur through suprafacial pathway.
If odd number of electron pair is involved then thermal reaction occur through suprafacial pathway and photochemical reactions occur through antarafacial pathway.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Predict the stereochemistry of the following Pericyclic reactions
a) a thermal [2 + 6] cycloaddition
b) photochemical [3 ,6] sigmatropic rearrangement
a) What product is formed from the [1,7] sigmatropic rearrangement of a deuterium in the following triene? (b) Does this reaction proceed in a suprafacial or antarafacial manner under thermal conditions? (c) Does this reaction proceed in a suprafacial or antarafacial manner under photochemical conditions?
What order of reagents should be used to synthesize the following product from methylcyclopentane?(A) Br2(B) Br2, hv(C) KOH, heat
Chapter 30 Solutions
Organic Chemistry
Ch. 30.1 - Prob. 1PCh. 30.3 - Prob. 2PCh. 30.3 - Prob. 3PCh. 30.4 - Prob. 4PCh. 30.6 - What stereochemistry would you expect for the...Ch. 30.6 - Prob. 6PCh. 30.7 - Prob. 7PCh. 30.8 - Propose a mechanism to account for the fact that...Ch. 30.8 - When a 2, 6-disubstituted allyl phenyl ether is...Ch. 30.9 - Prob. 10P
Ch. 30.SE - Predict the product obtained when the following...Ch. 30.SE - Prob. 12VCCh. 30.SE - The following rearrangement of N-allyl-N,...Ch. 30.SE - Plastic photochromic sunglasses are based on the...Ch. 30.SE - Prob. 15MPCh. 30.SE - Prob. 16MPCh. 30.SE - Prob. 17MPCh. 30.SE - Prob. 18APCh. 30.SE - Prob. 19APCh. 30.SE - Prob. 20APCh. 30.SE - Prob. 21APCh. 30.SE - Prob. 22APCh. 30.SE - Prob. 23APCh. 30.SE - Prob. 24APCh. 30.SE - Prob. 25APCh. 30.SE - Prob. 26APCh. 30.SE - Prob. 27APCh. 30.SE - Prob. 28APCh. 30.SE - Propose a pericyclic mechanism to account for the...Ch. 30.SE - Prob. 30APCh. 30.SE - Prob. 31APCh. 30.SE - Prob. 32APCh. 30.SE - Prob. 33APCh. 30.SE - Bicyclohexadiene, also known as Dewar benzene, is...Ch. 30.SE - Prob. 35APCh. 30.SE - Prob. 36APCh. 30.SE - The 1H NMR spectrum of bullvalene at 100 C...Ch. 30.SE - Prob. 38APCh. 30.SE - Prob. 39APCh. 30.SE - Prob. 40APCh. 30.SE - In light of your answer to Problem 30-40, explain...
Knowledge Booster
Similar questions
- What product(s) would you expect to obtain from reaction of 1, 3-cyclohexadiene witheach of the following?(a) 1 mol Br2in CH2Cl2(b) O3followed by Zn(c) 1 mol HCl in ether(d) 1 mol DCl in ether(e) 3-Buten-2-one (H2C = CHCOCH3)(f) Excess OsO4, followed by NaHSO3arrow_forwardElimination occurs when (Z)-3-bromohex-3-ene is treated with NaNH2. Under the same conditions, 1-bromocyclohexeneundergoes elimination much more sluggishly. Explain whyarrow_forwardWhich of the following best describes the stereochemistry of ring closure and the product for the following reaction? (3E,5Z,7E)-3,5,7-decatriene hv A) disrotatory, cis-5,6-diethyl-1,3-cyclohexadiene B conrotatory, cis-5,6-diethyl-1,3-cyclohexadiene disrotatory, trans-5,6-diethyl-1,3-cyclohexadiene conrotatory, trans -5,6-diethyl-1,3-cyclohexadienearrow_forward
- Predict the product of the following intramolecular (4+2) cycloaddition reaction.arrow_forwardGive the structures of A to E, showing the absolute stereochemistry in each case.arrow_forwardA student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a)Rank these three intermediates from most stable to least stable.arrow_forward
- Q6 Show how you would accomplish the follwoing transformations. (a) 2,2dibromobutane to but-1-yne (b) but-1-yne to oct-3-yne (c) trans-hex-2-ene to hex-2-yne (d) cyclodecyne to cis-cyclodecene (e) cyclodecyne to trans-cyclodecene (f) hex-1-yne to hexan-2-one, CH3COCH₂CH₂CH₂CH3 (g) hex-1-yn to hexanal, CH3(CH₂)4CHO (h) trans-hex-2-ene to cis-hex-2-enearrow_forward(2R,3S)-2-Bromo-3-phenylbutane undergoes an E2 elimination when treated with sodium methoxide. Draw all possible Newman projections for the bond relevant for the elimination reaction, and use those Newman projections to explain the stereochemical outcome of the reaction. Draw the final product and provide its IUPAC name.arrow_forwardHow can X be prepared from a constitutional isomer by a series of [2 + 2]cycloaddition reactions? Interest in molecules that contain severalcyclobutane rings fused together has been fueled by the discovery ofpentacycloanammoxic acid methyl ester, a lipid isolated from themembrane of organelles in the bacterium Candidatus Brocadiaanammoxidans. The role of this unusual natural product is as yetunknown.arrow_forward
- The 2 +2 cycloaddition of two molecules of (2E) -2- butenedinitrile leads to what product? Describe this process using a reaction scheme and curved arrows, show the product including the stereochemistry of the product.arrow_forward(a) Rank the following carbocations in order of increasing electrophilicity (1 = lowest electrophilicity, 4 = highest electrophilicity). (b) Rank the following 1,1-halomethylcyclopentanes in order of reactivity in an SN1 reaction (1 = lowest reactivity, 4 = highest reactivity. CH3 CI B with SNI, nor reactive means more stable (c) Rank the following species in terms of increasing nucleophilicity in an SN2 reaction in a po aprotic solvent (1 = lowest nucleophilicity, 4 = highest nucleophilicity).arrow_forwardThe alkyl halide cis-1-bromo-4-methycyclohexane (A) undergoes a (c) substitution reaction when treated with H,0 to give a racemic mixture which is made up of product B and C. (i) What is a racemic mixture? (ii) Draw all the possible diastereoisomers of the compound below. Br Brarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning