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
- 17-3 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_forward17-70 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_forward14-78 Consider alkenes A, B, and C. each of which has the same molecular formula, C(.H12. Alkenes B and C can each be separated into cis and trans isomers. Upon catalytic reduction using H,, in the presence of a transition metal catalyst (Ni, Pd, or Pt>, alkenes A, B, and C all give hexane as the only product. Acid- catalyzed hydration of alkene C gives one alcohol with the molecular formula CeH14O. Acid catalyzed- hydration of alkene B gives an equal mixture of two alcohols, each with the molecular formula C6H14O. Acid-catalyzed hydration of alkene C gives only a single alcohol with the molecular formula C6H14O. Propose structural formulas for alkenes A, B, and C and the alcohols formed by acid-catalyzed hydration of each, consistent with these experimental results.arrow_forward
- 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C) have about the same molecular weight, yet their boiling points differ by almost 50°C. Explain this fact.arrow_forward17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the acid catalyzed hydration of an alkene. Explain why it cannot be prepared from an alkene.arrow_forward17-36 Explain why the reduction of an aldehyde always gives a primary alcohol and the reduction of a ketone always gives a secondary alcohol.arrow_forward
- 13-20 Three products with the molecular formula CgH^BrCl form when bromobenzene is treated with chlorine, Cl2, in the presence of FeCl3 as a catalyst. Name and draw a structural formula for each product.arrow_forward13-57 Benzene, as we have seen in this chapter, is the simplest aromatic compound. Pyidine is an analog of benzene in which a CH group is replaced by a nitrogenarrow_forward17-62 Show how to bring about these conversions. In addition to the given starting material, use any other organic or inorganic reagents as necessary. (a) 1-Pentene to 2-pentanone (b) Cyclohexene to cyclohexanonearrow_forward
- Other than the aromatic ring, what functional group is present in the major organic product of the following reaction? Ophenol Oketone O aldehyde carboxylic acid + KMnO4 H₂Oarrow_forwardAcid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol oxygen to form an oxonium ion. Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction. н н :бн н Нас. Нас. CHз CH3 ČH3 CH3 3-methyl-2-butanol an oxonium ion Major Product Minor Product Minor Productarrow_forward14-49 Answer true or false. Today, the major carbon sources for the synthesis of methanol are coal and methane (natural gas), both nonrenewable resources. Today the major carbon sources for the synthesis of ethanol are petroleum and natural gas, both nonrenewable resources. Intermolecular acid-catalyzed dehydration of ethanol gives diethyl ether. Conversion of ethylene to ethylene glycol involves oxidation to ethylene oxide, followed by acid-catalyzed hydration (addition of water, to ethylene oxide. Ethylene glycol is soluble in water in all proportions. A major use of ethylene glycol is as automobile antifreeze.arrow_forward
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