Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 9PP
Practice Problem 14.9
In 1967 R. Breslow (of Columbia University) and co-workers showed that adding
(a) What new
(b) How many
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There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers.
Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm
Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppm
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGP
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- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.arrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardTreatment 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.arrow_forward
- (f) Methyl benzene (toluene) reacts with NO₂+ ions in strongly acidic solution, formed by a nitrating mixture of nitric acid and sulfuric acid. NO₂ 0 °C + NO₂* H* CH3 CH3 Name the aromatic product of this reaction (g) Draw the mechanism for this reaction using curly arrows (h) Sketch the ¹H NMR spectrum of phenol. Your answer should indicate the number of distinct ¹H environments (the multiplicity of each resonance peak is not required) (i) Predict, with reasoning, whether you expect the reactivity of phenol towards NO₂+ ions to be greater than the reaction involving methylbenzene. [word limit=50]arrow_forwardAddition of mesitylene to the strongly acidic solvent HF / SbF5 at -45 °C gives a new species which shows a 1H-NMR resonance at δ 4.67 (2H). Draw the structure of this species.arrow_forwardThe azo compound shown below has a λmax value of 410 nm. When treated with hydrogen in the presence of palladium on carbon, the λmax changes significantly. Suggest a reason for this observation and predict whether the λmax value increases or decreases.arrow_forward
- Addition of m-xylene to the strongly acidic solvent HF/SbF5 at -45°C gives a new species, which shows 1H-NMR resonances at d 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forwardThe primary amine isoamylamine (3-methylbutylamine) occurs naturally in a number of fruits and is used as a food flavouring: (CH3),CHCH,CH,NH, 3-methylbutylamine Suggest two ways in which it can be synthesised from suitable organic precursors. Note that only one of the two methods you propose may involve the reduction of another nitrogen containing compound. In each case, you should indicate what starting material and other reagents are needed, though details of precise experimental conditions or reaction mechanisms are not required.arrow_forwardGive mechanistic explanations for the following synthetic transformations.arrow_forward
- Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuranarrow_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is thestructure of R?arrow_forward(A) what is the hybridization of the nitrogen in each of the following compounds? (B) how does hybridization affect the availability of the lone pair and the basicity of each compound?arrow_forward
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