Package: Organic Chemistry With Connect 2-semester Access Card
4th Edition
ISBN: 9781259671838
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 18, Problem 18.74P
Interpretation Introduction
Interpretation:
The structure of BHT is to be predicted and a stepwise mechanism that illustrates its formation is to be drawn.
Concept introduction:
Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affordsBHT, a preservative with molecular formula C15H24O. BHT gives thefollowing 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0(singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT?Draw a stepwise mechanism illustrating how it is formed.
A student performed a reaction using 2-methoxyethanol as solvent under acid catalyst. When the solvent was redistilled, a higher boiling fraction (bp=162 °C) was also recovered. The mass spectrum showed a molecular ion at 134 m/z. The H nmr spectrum showed a triplet integrating for 2 at 3.55 ppm, a second triplet integrating for 2 at 3.65 ppm, and a singlet integrating for 3 at 3.4 ppm. Give the structure of the newly formed material that is consistent with this data.
A compound gives the following IR spectrum. Upon reaction with sodium borohydride followed by acidification, it forms the product with the 1H NMRspectrum shown below. Identify the starting material and the product.
Chapter 18 Solutions
Package: Organic Chemistry With Connect 2-semester Access Card
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - What acid chloride would be needed to prepare each...Ch. 18 - Prob. 18.7PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.9PCh. 18 - Prob. 18.10P
Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Classify each substituent as electron donating or...Ch. 18 - Prob. 18.15PCh. 18 - Label each compound as more or less reactive than...Ch. 18 - Rank the following compounds in order of...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Devise a synthesis of each compound from the...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Synthesize each compound from benzene.Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - Draw the products formed when phenol (C6H5OH) is...Ch. 18 - Prob. 18.37PCh. 18 - Draw the products of each reaction. a. e. i. b. f....Ch. 18 - What products are formed when benzene is treated...Ch. 18 - Draw the products of each reaction. a.d. b.e. c.f.Ch. 18 - You have learned two ways to make an alkyl...Ch. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.45PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - Which benzene ring in each compound is more...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Explain each statement in detail using resonance...Ch. 18 - Prob. 18.50PCh. 18 - Explain why the meta product is formed in the...Ch. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - Prob. 18.53PCh. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.60PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.62PCh. 18 - Prob. 18.63PCh. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from toluene (C6H5CH3)...Ch. 18 - Prob. 18.67PCh. 18 - Use the reactions in this chapter along with those...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.72PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - Prob. 18.74PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79PCh. 18 - Prob. 18.80P
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
- Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forwardAnethole, C10H12O, a major constituent of the oil of anise, has the 1H NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.arrow_forwardA 13C NMR spectrum of commercially available 2,4-pentanediol, shows five peaks at 23.3, 23.9, 46.5, 64.8, and 68.1 . Explain.arrow_forward
- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] withCH3CH2CH2MgBr, followed by aqueous acid, affords compound V, whichhas molecular formula C7H14O. V has a strong absorption in its IRspectrum 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), and2.60 (septet, 1 H) ppm. What is the structure of V?arrow_forwardAs a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde? (b) What was the other product?arrow_forwardReaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm−1 in its IR spectrum. F also shows eight lines in its 13C NMR spectrum, and gives the following 1H NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 18.arrow_forward
- Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm−1 or 3600-3200 cm−1, and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm. (a) Propose a structure for A, including stereochemistry. (b) Explain why B is the major product in this reaction.arrow_forwardTreatment 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_forwardan unknown compound of molecular formula C4H10O only showed singlets in its 1H-NMRarrow_forward
- A compound with molecular formula C5H10Br2 displays the following 13C NMR along with the DEPT-90 and DEPT-135 13CNMR spectra. What is the structure for this compound?arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.arrow_forwardWhat is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150–2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm?arrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY