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The stereochemistry of the products of reduction depends on the reagent used, as you learned in Sections 20.5 and 20.6. With this in mind, how would you convert
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Chapter 20 Solutions
Organic Chemistry - With Access (Custom)
- Cr(VI) compounds are common reagents for the oxidation of alcohols. Primary alcohols are oxidized to carboxylic acids and secondary alcohols are oxidized to ketones. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced Cr(IV) compound as the leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forwardA compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.arrow_forwardMany insects utilize cyclic ketal structures as pheromones such as the structure shown below. The biosynthetic pathway involves the cyclization of this acetal from the straight chain structure. Draw the straight chain structure that could be used to form this acetal. Use wedges and dashes to correctly depict the stereochemistry. H3C- >arrow_forward
- 1.Name and draw the products of each reaction. (a) 3-methyl oct-2-ene + hydrochloric acid (b) 2-fluoro-2-phenyl butanoic acid + ethanol → 1arrow_forwardName the following using IUPAC system of nomenclature: (a) CH2 (Cl) CH (NH2) CHO (b) CH3 C (Br) CH2 CH (F) COOH Brarrow_forward4) Provide the starting materials for the following reactions. a) b) c) HBr 0 °C H₂O, H₂SO4 NaOH (2 equivalents) H₂O, 55 °C OH Brarrow_forward
- (ii) Name the following using IUPAC system of nomenclature: (a) CH2 (Cl) CH (NH2) CHO (b) CH3 C (Br) CH2 CH (F) COOH Brarrow_forwardBent (D) Trigonal pyramidal 5. A student wishes to prepare ethyl acetate from the reaction of ethanol and acetic acid. To be successful, this reaction requires (A) an acidic catalyst. (C) an oxidizing agent. (B) a basic catalyst. (D) a reducing agent. 6. Which alkyl halide reacts most rapidly with aqueous sodium hydroxide solution? (A) CH₂Cl (B) CH₂I (C) (CH3)3CCH₂Cl (D) (CH3)3CCH₂I 57. How many isomers are there with the formula C6H₁4?arrow_forwardWhen the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forward
- A chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.arrow_forward3,4-Dimethylpent-1-ene has the formula CH2“CH¬CH(CH3)¬CH(CH3)2. When pure (R)-3,4-dimethylpent-1-ene is treated with hydrogen over a platinum catalyst, the product is (S)-2,3-dimethylpentane. The reactant is named (R), but the product is named (S). Does this name change imply a change in the spatial arrangement of the groups around the chiral center? So why does the name switch from (R) to (S)?arrow_forward4 But-2-enal, CH₂CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour. (a) But-2-enal exists as two stereoisomers. Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal. (b) (i) Describe a simple chemical test that would show that but-2-enal is an aldehyde. (ii) Explain why this test gives a different result with aldehydes than it does with keton (c) But-2-enal also reacts with sodium borohydride, NaBH4. (i) Identify the organic compound formed in this reaction. (ii) State the type of chemical reaction occurring. (d) Precautions must be taken to prevent but-2-enal catching fire. Construct a balanced equation for the complete combustion of but-2-enal, C₂HO.arrow_forward
- Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningChemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
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