Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 19.SE, Problem 67AP
Acid-catalyzed dehydration of 3-hydroxy-3-phenylcyclohexanone leads to an unsaturated
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can you draw each step on a piece of a paper please this is very confusing to me
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Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one step, by moderately heating
the reactants?
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•If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any arrangement you like.
• If your answer is no, check the box under the drawing area instead.
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Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Prob. 1PCh. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3PCh. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7PCh. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9PCh. 19.8 - Show the products you would obtain by...
Ch. 19.8 - Prob. 11PCh. 19.8 - Prob. 12PCh. 19.9 - Prob. 13PCh. 19.10 - Prob. 14PCh. 19.10 - Prob. 15PCh. 19.11 - What carbonyl compound and what phosphorus ylide...Ch. 19.11 - -Carotene, a yellow food-coloring agent and...Ch. 19.12 - Prob. 18PCh. 19.12 - Prob. 19PCh. 19.13 - Prob. 20PCh. 19.13 - Treatment of 2-cyclohexenone with HCN/KCN yields a...Ch. 19.13 - How might conjugate addition reactions of lithium...Ch. 19.14 - How might you use IR spectroscopy to determine...Ch. 19.14 - Prob. 24PCh. 19.14 - Prob. 25PCh. 19.14 - Prob. 26PCh. 19.SE - Each of the following substances can be prepared...Ch. 19.SE - Prob. 28VCCh. 19.SE - Prob. 29VCCh. 19.SE - Prob. 30MPCh. 19.SE - Prob. 31MPCh. 19.SE - Prob. 32MPCh. 19.SE - Prob. 33MPCh. 19.SE - Prob. 34MPCh. 19.SE - Prob. 35MPCh. 19.SE - It is not uncommon for organic chemists to prepare...Ch. 19.SE - Prob. 37MPCh. 19.SE - Prob. 38MPCh. 19.SE - Prob. 39MPCh. 19.SE - Prob. 40MPCh. 19.SE - Aldehydes and ketones react with thiols to yield...Ch. 19.SE - Prob. 42MPCh. 19.SE - When cyclohexanone is heated in the presence of a...Ch. 19.SE - Prob. 44MPCh. 19.SE - The Meerwein-Ponndorf-Verley reaction involves...Ch. 19.SE - Propose a mechanism to account for the formation...Ch. 19.SE - Prob. 47MPCh. 19.SE - Prob. 48MPCh. 19.SE - Treatment of an , -unsaturated ketone with basic...Ch. 19.SE - Prob. 50MPCh. 19.SE - Prob. 51MPCh. 19.SE - Prob. 52MPCh. 19.SE - Prob. 53MPCh. 19.SE - Prob. 54APCh. 19.SE - Draw and name the seven aldehydes and ketones with...Ch. 19.SE - Give IUPAC names for the following compounds:Ch. 19.SE - Draw structures of compounds that fit the...Ch. 19.SE - Predict the products of the reaction of (1)...Ch. 19.SE - Show how you might use a Wittig reaction to...Ch. 19.SE - How would you use a Grignard reaction on an...Ch. 19.SE - Prob. 61APCh. 19.SE - Prob. 62APCh. 19.SE - How would you synthesize the following substances...Ch. 19.SE - Carvone is the major constituent of spearmint oil....Ch. 19.SE - How would you synthesize the following compounds...Ch. 19.SE - At what position would you expect to observe IR...Ch. 19.SE - Acidcatalyzed dehydration of...Ch. 19.SE - Choose the structure that best fits the IR...Ch. 19.SE - Propose structures for molecules that meet the...Ch. 19.SE - Prob. 70APCh. 19.SE - Prob. 71APCh. 19.SE - When 4hydroxybutanal is treated with methanol in...Ch. 19.SE - Prob. 73APCh. 19.SE - Prob. 74APCh. 19.SE - Prob. 75APCh. 19.SE - Prob. 76APCh. 19.SE - Prob. 77APCh. 19.SE - Tamoxifen is a drug used in the treatment of...Ch. 19.SE - Compound A, MW 86, shows an IR absorption at 1730...Ch. 19.SE - Compound B is isomeric with A (Problem 19-79) and...Ch. 19.SE - The 1HNMR spectrum shown is that of a compound...Ch. 19.SE - Prob. 82APCh. 19.SE - Propose structures for ketones or aldehydes that...Ch. 19.SE - Prob. 84APCh. 19.SE - Prob. 85APCh. 19.SE - The proton and carbon NMR spectra for each of...Ch. 19.SE - The proton NMR spectrum for a compound with...
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- > For each pair of substrates below, choose the one that will react faster in a substitution reaction, assuming that: 1. the rate of substitution doesn't depend on nucleophile concentration and 2. the products are a roughly 50/50 mixture of enantiomers. Substrate A Substrate B Faster Rate X CI (Choose one) (Choose one) CI Br Explanation Check Br (Choose one) C 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy A F10arrow_forwardHow to draw this mechanism for the foloowing reaction in the foto. thank youarrow_forwardPredict the major products of the following organic reaction: Some important notes: CN A? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. No reaction. Explanation Check Click and drag to start drawing a structure. 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Centerarrow_forward
- Draw the major product of the following reaction. Do not draw inorganic byproducts. H3PO4 OHarrow_forwardPredict the major products of this organic reaction: HBr (1 equiv) Δ ? Some important notes: • Draw the major product, or products, of this reaction in the drawing area below. • You can draw the products in any arrangement you like. • Pay careful attention to the reaction conditions, and only include the major products. • Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. • Note that there is only 1 equivalent of HBr reactant, so you need not consider the case of multiple additions. Explanation Check X ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacyarrow_forwardFor the structure below, draw the resonance structure that is indicated by the curved arrow(s). Be sure to include formal charges. :ÖH Modify the second structure given to draw the new resonance structure. Include lone pairs and charges in your structure. Use the + and - tools to add/remove charges to an atom, and use the single bond tool to add/remove double bonds.arrow_forward
- Using the table of Reactants and Products provided in the Hints section, provide the major product (with the correct stereochemistry when applicable) for questions below by selecting the letter that corresponds to the exact chemical structures for the possible product. OH conc Hydrochloric acid 40°C Temp A/arrow_forwardUsing arrows to designate the flow of electrons, complete the reaction below and provide a detailed mechanism for the formation of the product OH conc Hydrochloric acid 40°C Temp All chemical structures should be hand drawn on a piece of paper Paragraph BI UAE +varrow_forwarddraw out the following structures plesearrow_forward
- Draw everything on a piece of paper outlining the synthesis from acetaldehyde to 2 cyclopentene carboxaldehyde using carbon based reagants with 3 carbons or fewers. Here is the attached image.arrow_forwardManoharan Mariappan, FR.D., 34) Complete the following reaction starting from hex-1-yne proceeding via different substitution reactions forming 2-heptanone. (25 pts). A Sia₂BH H₂O₂ NaOH Br D Mechanism for reaction D - ether-cleavage: 10 B Ph-MgCI, THF H₁₂O+ D HBr (XS) C TsCl, Py CH3-CH2-CH2-ONaarrow_forwardIn the table below, the correct structure for (2R)-3-methylpentan-2-ol (IUPAC name) can be represented by the letter OH OH HE > ' ÕH C B OH D A/ E OHarrow_forward
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