Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 13.6, Problem 18P
The reaction of (Z)-2-pentene with water and a trace of H2SO4 forms two products. Identity the products from their mass spectra
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Chapter 13 Solutions
Organic Chemistry (8th Edition)
Ch. 13.1 - Which of the following fragments produced in a...Ch. 13.2 - What distinguishes the mass spectrum of...Ch. 13.2 - What is the most likely m/z value for the base...Ch. 13.3 - Prob. 5PCh. 13.3 - a. Suggest possible molecular formulas for a...Ch. 13.3 - If a compound has a molecular ion with an...Ch. 13.3 - Identify the hydrocarbon that has a molecular ion...Ch. 13.4 - Predict the relative intensities of the molecular...Ch. 13.5 - Which molecular formula has an exact molecular...Ch. 13.5 - Prob. 11P
Ch. 13.6 - Sketch the mass spectrum expected for...Ch. 13.6 - The mass spectra of 1-methoxybutane,...Ch. 13.6 - Primary alcohols have a strong peak at m/z = 31....Ch. 13.6 - Identify the ketones responsible for the mass...Ch. 13.6 - Prob. 16PCh. 13.6 - Using curved arrows, show the principal fragments...Ch. 13.6 - The reaction of (Z)-2-pentene with water and a...Ch. 13.9 - a. Which is higher in energy: electromagnetic...Ch. 13.9 - Prob. 20PCh. 13.13 - Prob. 21PCh. 13.14 - Which occur at a larger wavenumber: a. the C O...Ch. 13.14 - Prob. 23PCh. 13.14 - Prob. 24PCh. 13.14 - Rank the following compounds from highest...Ch. 13.14 - Which shows an O H stretch at a larger...Ch. 13.16 - Prob. 27PCh. 13.16 - a. An oxygen-containing compound shows an...Ch. 13.16 - Prob. 29PCh. 13.16 - For each of the following pair of compounds, name...Ch. 13.17 - Which of the following compounds has a vibration...Ch. 13.17 - Prob. 32PCh. 13.18 - A compound with molecular formula C4H6O gives the...Ch. 13.20 - Prob. 34PCh. 13.20 - Prob. 35PCh. 13.21 - Predict the max of the following compound:Ch. 13.21 - Prob. 37PCh. 13.23 - a. At pH = 7 one of the ions shown here is purple...Ch. 13.23 - Prob. 39PCh. 13.23 - Prob. 40PCh. 13 - In the mass spectrum of the following compounds,...Ch. 13 - Prob. 42PCh. 13 - Draw structures for a saturated hydrocarbon that...Ch. 13 - Rank the following compounds in order of...Ch. 13 - For each of the following pairs of compounds,...Ch. 13 - a. How could you use IR spectroscopy to determine...Ch. 13 - Assuming that the force constant is approximately...Ch. 13 - Norlutin and Enovid are ketones that suppress so...Ch. 13 - In the following boxes, list the types of bonds...Ch. 13 - A mass spectrum shows significant peaks at m/z. =...Ch. 13 - Prob. 51PCh. 13 - Prob. 52PCh. 13 - Prob. 53PCh. 13 - The IR spectrum of a compound with molecular...Ch. 13 - Rank the following compounds from highest...Ch. 13 - Rank the following compounds from highest...Ch. 13 - What peaks in their mass spectra can be used to...Ch. 13 - Prob. 58PCh. 13 - Which one of the following five compounds produced...Ch. 13 - Prob. 60PCh. 13 - Each of the IR spectra shown below is accompanied...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - How can IR spectroscopy distinguish between...Ch. 13 - Prob. 65PCh. 13 - Prob. 66PCh. 13 - Give approximate wavenumbers for the major...Ch. 13 - Prob. 68PCh. 13 - Which one of the following live compounds produced...Ch. 13 - Phenolphthalein is an acid-base indicator. In...Ch. 13 - Prob. 71PCh. 13 - How can you use UV spectroscopy to distinguish...Ch. 13 - Prob. 73PCh. 13 - The IR and mass spectra for three different...
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- 7. What effect would you expect the following changes to have on the rate of the SN2 reaction of 1-iodo-2-methylbutane with cyanide ion? (a) The CN' concentration is halved, and the 1-iodo-2-methylbutane concentration is doubled. (b) Both the CN1 and the 1-iodo-2-methylbutane concentrations are tripled.arrow_forward(ii) Draw the product R, including a detailed reaction mechanism for the conjugate addition reaction between the 1,3-dicarbonyl P and the a,ß-unsaturated ketone Q. Eto P OEt + Q OEt Et3N R (iv) Explain why conjugate addition is favoured over direct addition to Q in this case.arrow_forwardTwo products are obtained from the reaction of (Z)-pent-2-ene with water in sulfuric acid. The mass spectra of these products are shown below. Draw the structure of each product, and match the product to its mass spectrumarrow_forward
- The reaction of methylpropene with HBr, under radical conditions, gives two intermediates. Propose a mechanism for the formation of the two products. Propose a mechanism for the following reaction and use electronic factors to account for the formation of a major product: CH2 CH2Br N-Bromosuccinimide (NBS) ho, CCI4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures o account for its stability.arrow_forwardOct-1-yne (HC≡CCH2CH2CH2CH2CH2CH3) reacts rapidty with NaH, forming a gas that bubbles out of the reaction mixture, as one product. Oct-1-yne also reacts rapidty with CH3MgBr, and a different gas is produced. Write balanced equations for both reactions and identify the gases formed.arrow_forwardThe reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.arrow_forward
- 134. The major product formed in the following reaction sequence is: OMe (1) (CF;CO),O; NE13 (A) (2) O3; Me,S MeOarrow_forwardRank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution: (a) C6H6, C6H5Cl, C6H5CHO; (b) C6H5CH3, C6H5NH2, C6H5CH2NH2.arrow_forwardThe treatment of (CH3)2C = CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its H NMR and IR spectra.arrow_forward
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