EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
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Chapter 23, Problem 20P
Propose structures for
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Alpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves
of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On
hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained.
Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the
following two compounds:
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CH3C-CH
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Propose a structure for alpha-phellandrene.
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HCCH₂CHCH
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CH(CH3)2
• 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.
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There are several isomeric alcohols and ethers of molecular formula C5H12O. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers.
Isomer A: δ = 0.92 (t, 7.8 Hz, 3 H), 1.20 (s, 6H), 1.49 (q, 7.8 Hz, 2H), 1.85 (s, 1H) ppm
Isomer B: δ = 1.19 (s, 9 H), 3.21 (s, 3H) ppm
Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.
Chapter 23 Solutions
EBK ORGANIC CHEMISTRY
Ch. 23 - Prob. 1PPCh. 23 - Prob. 2PPCh. 23 - Prob. 3PPCh. 23 - Prob. 4PPCh. 23 - Prob. 5PPCh. 23 - Prob. 6PPCh. 23 - Prob. 7PPCh. 23 - Prob. 8PPCh. 23 - Prob. 9PPCh. 23 - Prob. 10PP
Ch. 23 - Prob. 11PPCh. 23 - Prob. 12PPCh. 23 - Prob. 13PPCh. 23 - Prob. 14PCh. 23 - 23.15 How would you transform tetradecanal into...Ch. 23 - Prob. 16PCh. 23 - Prob. 17PCh. 23 - When limonene (Section 23.3) is heated strongly,...Ch. 23 - Gadoleic acid (C20H38O2), a fatty acid that can be...Ch. 23 - 23.20 -Phellandrene and -phellandrene are isomeric...Ch. 23 - Prob. 21PCh. 23 - Prob. 22PCh. 23 - Prob. 23PCh. 23 - The initial steps of a laboratory synthesis of...Ch. 23 - Prob. 25PCh. 23 - Prob. 26PCh. 23 - Prob. 27PCh. 23 - 2. The biosynthesis of fatty acids is accomplished...Ch. 23 - Prob. 3LGPCh. 23 - Prob. 4LGP
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- Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.arrow_forwardDeduce the structures of compounds A and B, two of the major components of jasmine oil, from the given data. Compound A: C9H10O2; IR absorptions at 3091–2895 and 1743 cm-1; 1H NMR signals at 2.06 (singlet, 3 H), 5.08 (singlet, 2 H), and 7.33 (broad singlet, 5 H) ppm. Compound B: C14H12O2; IR absorptions at 3091–2953 and 1718 cm-1; 1H NMR signals at 5.35 (singlet, 2 H) and 7.26–8.15 (multiplets, 10 H) ppm.arrow_forwardAn unknown compound has a molecular formula of C4H6O2. Its IR spectrum shows absorptions at 3095, 1762, 1254, and 1118 cm -1. It exhibits the following signals in its 1H NMR spectrum (ppm): 2.12 (singlet,3H), 4.55 (doublets of doublets, 1H), 4.85 (doublet of doublets, 1H), 7.25 (doublets of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 20.8, 100.4, 141.2, 168.0. Draw the structure of the unknown compoundarrow_forward
- Compounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forward
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