Compound W, C6H13Cl, undergoes base-promoted E2 elimination to give a single C6H12 alkene, Y. Compound X, C6H13Br, undergoes a similar reaction to form Y and an isomeric alkene Z. W is chiral; X is not. Catalytic hydrogenation of Y and Z produces 2-methylpentane. Propose structures for W and X. 0 . Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodleⓇ 24 On [F >

Compound W, C6H13Cl, undergoes base-promoted E2 elimination to give a single C6H12 alkene, Y. Compound X, C6H13Br, undergoes a similar reaction to form Y and an isomeric alkene Z. W is chiral; X is not. Catalytic hydrogenation of Y and Z produces 2-methylpentane. Propose structures for W and X. 0 . Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodleⓇ 24 On [F >

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter5: Stereochemistry At Tetrahedral Centers

Section5.SE: Something Extra

Problem 70AP

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Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle
You are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.
Compound A, C₂H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment, to give: O CH3 O || CH3CCH₂CCH₂CCH3 CH3 Compound A Propose a structure for A. • 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.
(R)-2-butanol reacts with phosphorus tribromide to give A (C4H9Br). Treatment of A with sodium cyanide in DMF gives B (C5H9)N. B is optically active. Draw the structure of B. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. Sn [F ? ChemDoodleⓇ
Compound W, C8H₁7Br, and X, CgH₁7Cl, are products of the radical bromination (W), and chlorination (X), of 2,4-dimethylhexane. W and X are each chiral. W reacts readily in water to form a chiral substitution product Y, CgH17OH. Reaction of a single enantiomer of W produces a single enantiomer of Y as the only substitution product. X likewise reacts readily in water though at a slower rate than W; a chiral substitution product Z, C8H₁7OH, is again formed. Unlike w, however, reaction of a single enantiomer of X produces Z that is nearly racemic. Propose structures for W and X. 0 • Do not use stereobonds in your answer. In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● +▾ 99.8) ChemDoodleⓇ + v ChemDoodleⓇ
New hydrocarbon compounds K, L, M and N have been formed from an organic reactions in Dr. Meredith laboratory. She found that compound K and L with molecular formula (C;H14) are unsaturated hydrocarbons with positional isomerism. Meanwhile, the reaction of hydrocarbon from compound M produces carbon dioxide and water when burns in plentiful oxygen. Another observation showed compound N produces three products X, Y and Z when react with chlorine gas in the presence of UV light. Identify the name of unsaturated hydrocarbon compound K and L and draw their possible condensed and skeletal structures. Suggest the IUPAC nomenclature name for compound M and write the complete chemical reaction of compound M when burns in plentiful oxygen. Show the complete mechanism reaction that occur for the formation of products X, Y and Z from compound N.
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Draw the structure of the following three isomeric esters with chemical formula C-H1,02. Ester #1: methyl cyclopentanecarboxylate Ester #2: propyl cyclopropanecarboxylate Ester #3: ethyl cyclobutanecarboxylate • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu.