Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 14, Problem 14.44SP
Interpretation Introduction
Interpretation: The information regarding the desired product using the spectroscopic characterisation is given. The structure corresponding to the product and the explanation corresponding to the observed spectra is to be identified.
Concept introduction: In IR spectroscopy, the vibration of atoms is measured. Lighter atoms and stronger bonds vibrate at a high wave number (stretching frequency).
In NMR spectroscopy, local magnetic field is observed around the atomic nuclei.
To determine: The structure corresponding to the product and the explanation corresponding to the observed spectra.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.
Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.
Predict the major organic product of the reaction sequence described.
Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2
(5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 hours. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over Na2SO4, solvent was removed and distillation gave the product
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A mixture will be fractionally distilled of cyclohexane and toluene. Samples will be analyzed using 13C NMR. Write an abstract stating whether the students were successful in isolating toluene from the mixture via distillation.arrow_forwardPls solve this question correctly in 5 min i will give u like for sure Balance the chemical equation of a reaction formed by the bromination of trans-cinnamic acid if we started with 0.3088 grams of trans cinnamic acid and 1mL of bromine. The product of this reaction is 2,3 - dibromo - 3- phenylpropanoic acidarrow_forwardConsider the monosubstituted benzene reagent X. Nitration of X yields product Y. Product Y is analysed by 1H and 13C NMR spectroscopy (see Figures 1 to 4). Determine the structure of X and Y on the basis of the spectral data provided.arrow_forward
- ›Predict the major organic product of the reaction sequence described. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)₂(5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 hours. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over Na₂ SO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143–1146.) Draw the major organic product. H₂O Harrow_forwardDraw a diagram similar to that in figure 6 detailing the separation of 1,2-dichlorobenzene, phenol (pka = 10), and pyridine by an extraction protocol. OH aa CI 1,2-dichlorobenzene phenol ·N·. pyridinearrow_forward22. Explain why the following compound cannot be converted to a Grignard reagent. How would you resolve this problem? O & Br O A dimer would form; treat C=0 with diol in acid Mg would react with C=0; treat C=0 with diol in acid A dimer would form; treat Br with diol in acid O Mg would react with C=0; treat Br with diol in acid MgBrarrow_forward
- Propose mechanisms to show the interchange of protons between ethanol molecules under base catalysis.arrow_forwardProvide a sequence of laboratory reactions which could be used to prepare 2-methylpropylmagnesium bromide ((CH3)2CHCH2MgBr) starting with 2-methylpropene. Your sequence must proceed through an alcohol as an intermediate product.arrow_forwardThe following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forward
- 1. In the reactions involving the three isomeric alcohols with the formula C4H9OH, describewhat each of the following tests showed about reactivity of the -OH group and reactions of 1°,2°, and 3° alcohols.• the test with neutral KMnO4• the test with concentrated HCl2. Predict how the fourth alcohol with the formula C4H10O would react if tested with:• 0.01 M KMnO4• concentrated HCl at room temperatureExtend FurtherUse your observations of the solutions formed in the previous experiments and yourunderstanding of alcohols to complete a table like the one shown below. Research the meltingand boiling points to verify your answers.arrow_forwardVanillin, NaI/NaOCL, ethanol/H2O, bleach are reacted in an electrophilic aromatic substitution leading to the product 5-Iodovanillin. Please help me by drawing out a separation scheme. I need to see where each compound ends up leading up to the final product as it is being made into a solid precipitate.arrow_forwardWhat was the major product?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY