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Concept explainers
(a)
Interpretation: A stepwise mechanism for the given reaction is to be drawn.
Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of
(b)
Interpretation: The rearrangement product formed from
Concept introduction: Pinacol rearrangement is also termed as Pinacol-Pinacolone rearrangement. This rearrangement reaction is an acid catalyzed conversion of
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Chapter 9 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
- The cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.arrow_forwardDraw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.arrow_forward2. Draw one enol tautomer of each of the following ketones and aldehydes. a) b) c) of مل G Harrow_forward
- Draw the structure of each of the following molecules. (a) pentanoyl chloride; (b) 4-(2-methylpropyl)heptanedioyl chloride; (c) (S)-5-phenyloctanoyl chloridearrow_forwardDraw the structure of each of the following molecules. (a) pentanoyl chloride; (b) 4-(2-methylpropyl)heptanedioyl chloride;(c) (S)-5-phenyloctanoyl chloridearrow_forwardA) An Alcohol X has the structure of (CH,), C(OH)CH(CH,),. i) State the IUPAC name of alcohol X. i) Outline the mechanism for the reaction occurring when alcohol X is converted into 2,3-dimethylbut-2-ene in the presence of a strong acid. i) Name the reaction in part ii). iv) Draw the structure and state the IUPAC name of an isomer of 2,3-dimethyl-2- butene which is also formed in the reaction. v) Explain why two products are obtained. vi) Write an equation for the reaction between alcohol X and ethanoyl chloride. vii) Outline a mechanism for this reaction, using ROH to represent the alcohol in the mechanism.arrow_forward
- 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.) Propenearrow_forwardDraw the molecule that corresponds to each IUPAC name. (a) 3,3-dipropoxypentan-1-amine; (b) 2,3,4-trichlorocyclohexanol; (c) 3-cyclopropylpentan-1-ol; (d) 3-(1-methylethyl)cycloheptanaminearrow_forward(a) What is the major alkene formed when A is dehydrated with H2SO4? (b) What is the major alkene formed when A is treated with POCl3 and pyridine? Explain why the major product is different in these reactions.arrow_forward
- PGF2α (Section 4.15) is synthesized in cells using a cyclooxygenase enzyme that catalyzes a multistep radical pathway. Two steps in the pathway are depicted in the accompanying equations. (a) Draw in curved arrows to illustrate how C is converted to D in Step [1]. (b) Identify Y, the product of Step [2], using the curved arrows that are drawn on compound D.arrow_forwardWrite the IUPAC name of each alkene. (a) (b) uarrow_forwardConsider the tricyclic structure A. (a) Label each substituent on the rings as axial or equatorial. (b) Draw a skeletal structure for A, using wedges and dashed wedges to show whether the substituents are located above or below the rings.arrow_forward
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
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