Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 30.SE, Problem 34AP
Bicyclohexadiene, also known as Dewar benzene, is extremely stable despite the fact that its rearrangement to benzene is energetically favored. Explain why the rearrangement is so slow.
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A novel heterocyclic compound, M, contains nitrogen and sulfur atoms and exhibits interesting photochemical properties. When exposed to ultraviolet (UV) light at a specific wavelength, M undergoes a photoreaction resulting in two products: N and O. Product N is formed through a [2+2] cycloaddition involving the nitrogen atom in M, while product O results from a homolytic cleavage of a sulfur-sulfur bond in M. Given these reaction pathways, what is the most probable structure of M, and what are the likely structures of N and O? A. M is a thiazole derivative; N is a dimerized product through the nitrogen atoms, and O is a compound with two sulfur-centered radicals. B. M is a diazine derivative; N is a tetra-atomic cyclic compound, and O is a compound with two separate thiol groups. C. M is a thiadiazole derivative; N is a four-membered ring involving the nitrogen atom, and O results in two sulfur-centered radicals. D. M is a dithiolane derivative; N is a dimer involving the nitrogen…
When bromine adds to the double bond in a cyclohexene, the resulting
dibromide is trans. This stereochemistry is due to:
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c) Markovnikov’s rule d) Zaitsev’s rule
Draw the alkene that would react with the reagent given to account for the product formed.
? +
+
H₂O
****
H₂S04
• You do not have to consider
stereochemistry.
• You do not have to explicitly draw H atoms.
• In cases where there is more than one answer, just draw one.
CH3
CH3 CHCCH3
| |
OH CH3
+1
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...
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- 2. Explain the selectivity of the following reaction, which produces a single product despite both alkene carbons being equally substituted. H3C CF3 HBr CF3 H3C CF3 H3C Br- H3C only product -H CF3arrow_forwardExplain why the bond dissociation enthalpy of a C-H bond in benzene is significantly greater than that in alkanesarrow_forwardThe major product of the following reaction exists as two stereoisomers. Draw both isomers: show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry (you don’t need to draw wedge and dash bonds for C-H bonds of CH3 and CH2 groups). Assign stereo configuration of the asymmetric carbon atoms and write the relationship between two isomers.arrow_forward
- The compound below is treated with chlorine in the presence of light. CH3 CH3CHCH₂CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. n [ ]# ?arrow_forwardDehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.arrow_forwardWhich of the following statements about cycloaddition reactions is not true? Cycloaddition reactions form a cyclic product with two new bonds. The course of the reaction is determined by the symmetry of the molecular orbitals of the products. Cycloaddition reactions are concerted. Cycloaddition reactions are stereospecific.arrow_forward
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