Concept explainers
(a)
Interpretation:
Why
Concept introduction:
Organic compounds that are not aromatic are comparatively less stable than
(b)
Interpretation:
Geometry of the dianion
Concept introduction:
Aromatic compounds are chemical compounds that contain conjugated planar ring systems with delocalized pi electron clouds instead of discrete alternating single and double bonds.
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Chapter 14 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.) cis-2-Butenearrow_forwardWhen alkyne A is treated with NaNH2 followed by CH3I, a product having molecular formula C6H10O is formed, but it is not compound B. What is the structure of the product, and why is it formed?arrow_forward1. what are the differences between acyclic and cyclic forms in terms of their physical properties? 2. what is the role of vinegar in liquid-liquid extraction?arrow_forward
- A compound X of molecular formula C7H14 when hydrogenated produces 2,4-dimethylpentane and when hydroborated the obtained alcohol is 2,4-dimethyl-1-pentanol. a. What is the structure of X? b. If X is reacted with H2O catalyzed by H2SO4, what product is obtained? Write the structure, give the name, and write the complete mechanism, step by step of this reaction, in such a way as to explain the formation of the compound (DO NOT FORGET THE CORRECT USE OF ARROWS!).arrow_forwardAn unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst to give hydrocarbon B. Hydrocarbon A also reacts with OsO4 to give the glycol C. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2COOH, and the other fragment is ketone D (R2C=O). What are the structures of A, B, C and D? Write all reactions.arrow_forwardstructural formula (3E, 6S)-6, 7, 7-trimethyl-4-phenyloct-3-enoic acidarrow_forward
- Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)arrow_forwardDraw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forwardThe heat of combustion of decahydronaphthalene(C10H18) is -6286 kJ/mol. The heat of combustion ofnaphthalene (C10H8) is -5157 kJ/mol. (In both casesCO2(g) and H2O(l) are the products.) Calculate the heat of hydrogenationand the resonance energy of naphthalene.arrow_forward
- Draw the carbocation you'd expect from the reaction of 2-chloro-3-methylbutane with AlCl3?arrow_forwardGive two examples of reactions of alkenes that result in Anti-Markonikov’s addition productsarrow_forwarddraw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocationarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning