Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 13, Problem 13.54P
Reaction of
gives the IR and mass spectra shown below. Propose a structure for
a stepwise mechanism that accounts for its formation.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z = 150 and a base peak at 121. The 1H NMR spectrum of D is shown below. What is the structure of D?
The treatment of isoprene [CH2=C(CH3)CH=CH2] with one equivalent of mCPBA forms A as the major product. A gives a molecular ion at 84 in its mass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1H NMR spectrum of A is given below. What is the structure of A?
Treatment of W with CH3Li, followed by CH3I, affords compound Y (C7H14O) as the major product. Y shows a strong absorption in its IR spectrum at 1713 cm−1, and its 1H NMR spectrum is given below. (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.
Chapter 13 Solutions
Organic Chemistry-Package(Custom)
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Prob. 13.3PCh. 13 - What molecular ions would you expect for the...Ch. 13 - The mass spectrum of 2,3-dimethylpentane also...Ch. 13 - The base peak in the mass spectrum of 2, 2,...Ch. 13 - (a) What mass spectral fragments are formed by ...Ch. 13 - What cations are formed in the mass spectrometer...Ch. 13 - The low-resolution mass spectrum of an unknown...Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...
Ch. 13 - Prob. 13.11PCh. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - How do the three isomers of molecular formula...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Prob. 13.20PCh. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - What molecular ion is expected for each compound?Ch. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Match each structure to its mass spectrum. a. b....Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.32PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - Can the exact mass obtained in a high-resolution...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - Which of the highlighted bonds absorbs at higher v...Ch. 13 - What major IR absorptions are present above...Ch. 13 - How would each of the following pairs of compounds...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - Prob. 13.42PCh. 13 - 13.47 Match each compound to its IR spectrum
Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.49PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.52PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.56PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
Additional Science Textbook Solutions
Find more solutions based on key concepts
22.102 Write the structures of the cis and tram isomers, if any, for the following compounds:
Chemistry: The Molecular Nature of Matter
16.43 The following pictures represent solutions at various stages in thetitration of a weak diprotic acid with...
Chemistry (7th Edition)
What is the pH range for acidic solutions? For basic solutions?
Introduction to Chemistry
For each of the following 2-dimensional shapes, determine the highest order rotation axis of symmetry.
Inorganic Chemistry
Fully developed conditions are known to exist for water flowing through a 25-nim-diameer tube at 0.01 kg/s and ...
Fundamentals of Heat and Mass Transfer
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (13th Edition)
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
- Compound A, MW 86, shows an IR absorption at 1730 cm-1 and a very simple 1H NMR spectrum with peaks at 9.7 (1 H, singlet) and 1.2 (9 H, singlet). Propose a structure for A.arrow_forwardThe 1H and 13C NMR spectra below belong to a compound with formula C6H10O2. Propose a structure for this compound.arrow_forwardTreatment of W with CH3Li, followed by CH3I, affords compound Y (C7H14O) as the major product. Y shows a strong absorption in its IR spectrum at 1713 cm−1, and its 1H NMR spectrum is given below, (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.arrow_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2, −OH to yield compound Y (molecular formula C10H14). Based on the 1HNMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardTreatment of W with CH3Li, followed by CH3I, affords compound Y(C7H14O) as the major product. Y shows a strong absorption in its IRspectrum at 1713 cm−1, and its 1H NMR spectrum is given below. (a)Propose a structure for Y. (b) Draw a stepwise mechanism for theconversion of W to Y.arrow_forwardpropose a synthesis from benzenearrow_forward
- Choose the best reagents to complete the following reaction. (CH2OH)2, TSOH OH OH A NaOH B H2O Q C H2, Raney nickel D TSOH, H2O E (CH2OH)2, TSOHarrow_forwardProvide the correct product for the following series of transformations. Hint: The product has a 1H NMR spectrum with only 2 resonances with relative H integrations of 3:1.arrow_forwardTreatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products (M and N) with molecular formula C6H12. The 1H NMR spectra of M and N are given below. Propose structures for M and N, and draw a mechanism to explain their formation.arrow_forward
- Anethole, 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_forwardShow how the following compound could be prepared by a Suzuki reaction (Bn = benzyl).arrow_forwardNitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?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
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY