Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 17.SE, Problem 48AP
How would you prepare the following compounds from 1-phenylethanol? More than one step may be required.
(a) Acetophenone(PhCOCH3)
(b) Benzyl alcohol
(c) m-Bromobenzoic acid
(d) 2-Phenyl-2-propanol
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0-
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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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- Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (c) Ethyl 2-rnethylbutanoate (d) Ethyl 2,2-dimethylpropanoate (b) Ethyl 3-methylbutanoatearrow_forwardDraw the line structures and provide common names for the following ketones: (a) 1-Phenylpropanone (b) 2-Methylpentan-3-one(c) 1-Cyclohexyl-3,3-dimethylbutan-2-onearrow_forward14. What is the IUPAC name for the following compound? NH- (a) propyl propanamide (b) propyl propanoate (c) N-propylptopanamine. (d) N, N-propylpropanamide (e) N-propxlpropanamidearrow_forward
- 16) The best classification for the following compound is: O 0 A) aldehyde B) ester C) ketone D) carboxylic acid 17) The name of the following compound: A) phenyl ethanoate B) phenyl propanoate C) propyl benzoate D) butyl benzoate 18) Complete the following reaction: CH3COOC₂H5 + NaOH- A) CH3COCH 3 B) CH3COCH₂CH3 C) CH3COONa D) CH3COOCH₂ من + HOC₂H5.arrow_forward17-48 How would you prepare the following compounds from More than one step may be required. 1-phenylethanol? (a) Acetophenone (PhCOCH3) (b) Benzyl alcohol (c) m-Bromobenzoic acid (d) 2-Phenyl-2-propanol 17-49 How would you prepare the following substances from cyclopentanol? More than one step may be required. (a) Cyclopentanone (b) Cyclopentene (c) 1-Methylcyclopentanol (d) trans-2-Methylcyclopentanol 17-50 What products would you expect to obtain from reaction of 1-methyl- cyclohexanol with the following reagents? (a) HBr (b) NaH (c) H₂SO4 (d) Na₂Cr₂O7arrow_forward1. Draw structures corresponding to the following IUPAC names: (a) 4-Methylpentanoic acid (b) o-Hydroxybenzoic acid (c) 2,2-Dimethylpropanoyl chloride (d) trans-2-Methylcyclohexanecarboxamide (e) p-Methylbenzoic anhydride (f) p-Bromobenzonitrilearrow_forward
- How will you convert the following: (i) acetone to chloroform (ii) acetylene to acetic acid (iii) formaldehyde to 1-propanol (iv) acetophenone to 2-phenyl-2-butanol.arrow_forwardPredict the products formed when m-cresol (m-methylphenol) reacts with(a) NaOH and then ethyl bromide (arrow_forwardWhich is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forward
- What is the major product of the following reaction? (a) (b) 37 HO HO (c) HO NaOH EtOH ? (d) HOarrow_forwardDevise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.(a) 1-methylcyclohexanol (b) cyclohexylmethanol(c) 1-(hydroxymethyl)cyclohexanol (d) trans-2-methylcyclohexanol(e) 2-chloro-1-methylcyclohexanol (f) 1-(phenylmethyl)cyclohexanolarrow_forwardHow would you carry out the following reactions? More than one step may be required. (a) 3-Hexyne →→ 3-Hexanone (b) Benzene →→ m-Bromoacetophenone (c) Bromobenzene →→ Acetophenone (d) 1-Methylcyclohexene →→ 2-Methylcyclohexanonearrow_forward
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