Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 15, Problem 15.31P
Interpretation Introduction
Interpretation:
The longest-wavelength absorption of
Concept introduction:
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Why benzene absorbs at 254 nm in the UV and phenol C6H5OH absorbs at 280 nm?
Cyclohexene has the formula C6H1o and the structure shown in Figure 4-4. When cyclohexene is treated with acid and water it forms Compound A with the formula C6H12O. When Compound A is treated with an oxidizing agent, it forms Compound B with the formula C6H100.
IR spectra for Compounds A and B are shown in Figure 4-3. The best structure
for A is
The best for B is
Which molecule will absorb the longest wavelength in UV ? 1,3 cyclohexadiene or 1,4 cyclohexadiene? Explain
Chapter 15 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42PCh. 15 - Prob. 15.43PCh. 15 - Prob. 15.44PCh. 15 - Prob. 15.45PCh. 15 - Prob. 15.46PCh. 15 - Prob. 15.47PCh. 15 - Prob. 15.48PCh. 15 - Prob. 15.49PCh. 15 - Prob. 15.50PCh. 15 - Prob. 15.51PCh. 15 - Prob. 15.52PCh. 15 - Prob. 15.53PCh. 15 - Prob. 15.54PCh. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - Prob. 15.57PCh. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - Prob. 15.60PCh. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - Prob. 15.63PCh. 15 - Prob. 15.64PCh. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - Prob. 15.67PCh. 15 - Prob. 15.68PCh. 15 - Prob. 15.1YTCh. 15 - Prob. 15.2YTCh. 15 - Prob. 15.3YTCh. 15 - Prob. 15.4YTCh. 15 - Prob. 15.5YTCh. 15 - Prob. 15.6YTCh. 15 - Prob. 15.7YTCh. 15 - Prob. 15.8YTCh. 15 - Prob. 15.9YTCh. 15 - Prob. 15.10YTCh. 15 - Prob. 15.11YTCh. 15 - Prob. 15.12YTCh. 15 - Prob. 15.13YTCh. 15 - Prob. 15.14YTCh. 15 - Prob. 15.15YTCh. 15 - Prob. 15.16YTCh. 15 - Prob. 15.17YTCh. 15 - Prob. 15.18YTCh. 15 - Prob. 15.19YTCh. 15 - Prob. 15.20YTCh. 15 - Prob. 15.21YTCh. 15 - Prob. 15.22YTCh. 15 - Prob. 15.23YTCh. 15 - Prob. 15.24YTCh. 15 - Prob. 15.25YTCh. 15 - Prob. 15.26YTCh. 15 - Prob. 15.27YTCh. 15 - Prob. 15.28YTCh. 15 - Prob. 15.29YTCh. 15 - Prob. 15.30YT
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- Please explain why if the 13C & 1H NMR spectrum data below is the possible structure of known compound ' 1-(4'-methyl-[1,1'-biphenyl]-4-yl)ethanone'? (Suzuki Cross-Coupling) 1H NMR: 2.41 ppm, 3H, singlet, aromatic -CH3 2.64 ppm, 3H, singlet, ketone, -CH3 7.27-7.29 ppm, 2H,doublet, aromatic -CH 7.53-7.54 ppm, 2H,doublet, aromatic -CH 7.67-7.68 ppm, 2H,doublet, aromatic -CH 8.01-8.03 ppm, 2H,doublet, aromatic -CH 13C NMR 22 ppm, -CH3 attached to the aromatic ring 26 ppm, -CH3 attached to the ketone carbonyl 127 ppm, aromatic -CH 129 ppm, aromatic -CH 130.5 ppm, aromatic -CH 135 ppm, aromatic -CH 137 ppm, aromatic -CH 145 ppm, aromatic -CH 197 ppm, carbonyl carbon of ketone IR: A band at 3040 cm-1 is a stretching frequency of the C-H bond of the alkene. A band at 1672 cm-1 is a stretching frequency of the -C=O bond of ketone (alpha beta unsaturated ketone). A band at 1598 cm-1 is a stretching frequency of the C=C bond of the aromatic ring. A band at 1391 and 1362 cm-1 is a bending…arrow_forwardPropose a structure consistent with each set of data.a.) C9H10O2: IR absorption at 1718 cm−1 b.) C9H12: IR absorption at 2850–3150 cm−1arrow_forwardWhich of the following molecules would have 5 peaks in its 13C NMR spectrum? (Could be multiple) a.) cyclohexane b.) 3-methylpentane c.) 1,3-dimethylcyclobutane d.) methylcyclohexane e.) 2,2-dimethylpentane f.) 1-chloro-2-methylcyclopentanearrow_forward
- 5. Which of the following is True and which one is False? The IR spectrum of 1-hexene has more peaks than its UV spectrum. The n---π for acrolein (CH2=CH=O) has shifted to a shorter wavelength, compared to propanal.arrow_forwardy-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since y-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. y-Butyrolactone shows an absorption in its IR spectrum at 1770 cm-1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of y-butyrolactone?arrow_forward1. An aliphatic ketone absorbs at 1,715 cm-1. What is the frequency of this vibration in hertz, which is cycles per second or just per second, reciprocal seconds? 2. What is the energy equivalent of this stretching vibration in kcal/mole? 3. Why does 3,4-diethyl-3-hexene not have a carbon to carbon double bond stretching absorption band? 4. Why does a carbon to oxygen double bond absorption band have a greater intensity than a carbon to carbon double bond absorption band? 5. Using only IR, explain in detail how one could most easily differentiate between oct-1-ene and oct-1-yne if all carbon to carbon bonds are ignored. 6. Using only IR, explain in detail how one could most easily differentiate between butan-1-ol and butanoic acid.arrow_forward
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