Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 17.SE, Problem 39AP
Interpretation Introduction
Interpretation:
Which of the eight alcohols, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 3-methyl-2 butanol, 3-methyl-1-butanol and 2,2-dimethyl-1-propanol, react with CrO3 in aqueous acid is to be stated and the product expected from each reaction is also to be given.
Concept introduction:
CrO3 in aqueous acid oxidizes 10 alcohols to
To state:
Which of the eight alcohols, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 3-methyl-2 butanol, 3-methyl-1-butanol and 2,2-dimethyl-1-propanol, react with CrO3 in aqueous acid and to predict the product expected from each reaction.
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Chapter 17 Solutions
Organic Chemistry
Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2PCh. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5PCh. 17.3 - Prob. 6PCh. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8PCh. 17.5 - Prob. 9PCh. 17.5 - Prob. 10P
Ch. 17.5 - Use the reaction of a Grignard reagent with a...Ch. 17.6 - How would you carry out the following...Ch. 17.6 - What products(s) would you expect from dehydration...Ch. 17.7 - What alcohols would give the following products on...Ch. 17.7 - What products would you expect from oxidation of...Ch. 17.8 - TMS ethers can be removed by treatment with...Ch. 17.9 - Show the mechanism for the reaction of...Ch. 17.11 - Prob. 18PCh. 17.11 - When the 1HNMR spectrum of an alcohol is run in...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw the structure of the carbonyl compound(s)...Ch. 17.SE - Prob. 22VCCh. 17.SE - Prob. 23VCCh. 17.SE - Name and assign R or S stereochemistry to the...Ch. 17.SE - Evidence for the intermediate carbocations in the...Ch. 17.SE - Acid-catalyzed dehydration of 2,...Ch. 17.SE - Prob. 27MPCh. 17.SE - Treatment of the following epoxide with aqueous...Ch. 17.SE - Prob. 29MPCh. 17.SE - Prob. 30MPCh. 17.SE - Identify the type of substitution mechanism (SN1,...Ch. 17.SE - The conversion of 3 alcohols into alkenes under...Ch. 17.SE - Prob. 33MPCh. 17.SE - The trimethylsilyl (TMS) protecting group is one...Ch. 17.SE - When the alcohol below is treated with POCI3 and...Ch. 17.SE - Phenols generally have lower pKa’s than...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw and name the eight isomeric alcohols with...Ch. 17.SE - Prob. 39APCh. 17.SE - Named bombykol, the sex pheromone secreted by the...Ch. 17.SE - Carvacrol is a naturally occurring substance...Ch. 17.SE - What Grignard reagent and what carbonyl compound...Ch. 17.SE - What carbonyl compounds would you reduce to...Ch. 17.SE - What carbonyl compounds might you start with to...Ch. 17.SE - Prob. 45APCh. 17.SE - What products would you obtain from reaction of...Ch. 17.SE - Prob. 47APCh. 17.SE - How would you prepare the following compounds from...Ch. 17.SE - Prob. 49APCh. 17.SE - What products would you expect to obtain from...Ch. 17.SE - Prob. 51APCh. 17.SE - Propose structures for alcohols that have the...Ch. 17.SE - Propose a structure consistent with the following...Ch. 17.SE - The 1HNMR spectrum shown is that of...Ch. 17.SE - A compound of unknown structure gave the following...Ch. 17.SE - Propose a structure for a compound C15H24O that...Ch. 17.SE - Prob. 57APCh. 17.SE - Prob. 58APCh. 17.SE - Rank the following substituted phenols in order of...Ch. 17.SE - Benzvl chloride can be converted into benzaldehvde...Ch. 17.SE - Prob. 61APCh. 17.SE - Prob. 62APCh. 17.SE - Prob. 63APCh. 17.SE - Prob. 64APCh. 17.SE - Prob. 65APCh. 17.SE - Prob. 66APCh. 17.SE - Dehydration of trans-2-methylcyclopentanol with...Ch. 17.SE - 2, 3-Dimethyl-2, 3-butanediol has the common name...Ch. 17.SE - As a rule, axial alcohols oxidize somewhat faster...Ch. 17.SE - Prob. 70APCh. 17.SE - A problem often encountered in the oxidation of...Ch. 17.SE - Identify the reagents a-f in the Following scheme:Ch. 17.SE - Prob. 73APCh. 17.SE - Prob. 74APCh. 17.SE - Compound A, C8H10O, has the IR and 1H NMR spectra...Ch. 17.SE - Prob. 76APCh. 17.SE - Prob. 77AP
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Similar questions
- 17-36 Explain why the reduction of an aldehyde always gives a primary alcohol and the reduction of a ketone always gives a secondary alcohol.arrow_forward17-70 What simple chemical test could you use to distinguish between the members of each pair of com pounds? Tell what you would do, what you would expect to observe, and how you would interpret your experimental observation. (a) Benzaldehyde and cyclohexanone (b) Acetaldehyde and acetonearrow_forward17-73 Alcohols can be prepared by the acid-catalyzed hydration of alkenes (Section 12-6B) and by the reduction of aldehydes and ketones (Section 17-4B). Show how you might prepare each of the following alcohols by (1) acid-catalyzed hydration of an alkene and (2) reduction of an aldehyde or a ketone. (a) Ethanol (b) Cyclohexanol (c) 2-Propanol (d) 1-Phenylethanolarrow_forward
- 17-26 Account for the fact that acetone has a higher boiling point (56°C) than ethyl methyl ether (11°C) even though their molecular weights are almost the same.arrow_forward17-3 1 Draw a structural formula for the principal organic product formed when each compound is treated with K2Cr2O7/H2SO4. If there is no reaction, say so. (a) Butanal (b) Benzaldehyde (c) Cyclohexanone (d) Cyclohexanolarrow_forward17-33 What simple chemical test could you use to distinguish between the members of each pair of com pounds? Tell what you would do, what you would expect to observe, and how you would interpret your experimental observation. (a) Pentanal and 2-pentanone (b) 2-Pentanone and 2-pentanolarrow_forward
- In addition to not undergoing substitution reactions, the alkyl bromide shown in Problem 11-32 also fails to undergo an elimination reaction when treated with base. Explain.arrow_forwardPropyl alcohol will be oxidized to propanaldehyde using I. PCC II. LiAlH4 III. NaBH4 IV. KMnO4arrow_forwardGive the structures of the products you would expect when each alcohol reacts with (1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2. (a) 2,2-dimethylbutan-1-ol (b) cis-3-methylcyclopentanolarrow_forward
- Show the reagents required to form the primary alcohol in each of the following reactions. Which of the reactions cannot be used for the synthesis of isobutyl alcohol?arrow_forwardTrue or False1. As the alkyl chain increases in molecular weight among primary alcohol, the solubility in water increases2. An ethoxide ion exhibits greater proton-accepting property compared to an ethyloxonium ion3. Phenol is mroe acidic than cyclohexyl alcohol due to the electron-donating ability of phenolic oxygenarrow_forwardPredict the major products formed when benzene reacts (just once) with the following reagents. isobutyl alcohol + BF3arrow_forward
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