Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 9, Problem 31P
What are the masses and structures of the ions produced in the following cleavage pathways?
(a)
(b) dehydration of cyclopentanol;
(c) McLafferty rearrangement of 4-methyl-2-octanone (two pathways)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Draw the structures, including stereochemistry, of the major products (A) from the re-
action between 1-pentene and mercury(II) acetate in methanol. Assign the configura-
tions (R or S) of any stereocenters. Draw the structures, including stereochemistry, of
the products (B) obtained from demercuration of A with sodium borohydride
(NaBH4); assign the configurations of the stereocenters.
Hg(OAc)₂
CH₂OH
A
NaB H₁
H₂O, EtOH
B
Write a reasonable mechanism for the following transformation.
In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Locate the nine abdominopelvic regions and the four abdominopelvic quadrants on yourself, and list some of the ...
Principles of Anatomy and Physiology
40. Use the Henderson–Hasselbalch equation to calculate the pH of each solution.
a. a solution that is 0.145 M ...
Chemistry: A Molecular Approach (4th Edition)
2. Define equilibrium population. Outline the conditions that must be met for a population to stay in genetic e...
Biology: Life on Earth (11th Edition)
1. Which parts of the skeleton belong to the appendicular skeleton? Which belong to the axial skeleton?
Human Anatomy & Physiology (2nd Edition)
A 2500Ibm car moving at 25mi/h is accelerated at a constant rate of 15ft/s2 up to a speed of 50mi/h . What are ...
Fundamentals Of Thermodynamics
What type of unconformity separates layer G from layer F?
Applications and Investigations in Earth Science (9th 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
- Propose a mechanism for the conjugate addition of a nucleophile ( Nuc:" ) to acrylonitrile ( CH,=CHCN ). Use resonance forms to show how the cyano group activates the double bond for conjugate addition.arrow_forwardIllustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forward(a)Which compound/s will produce an orange precipitate upon reaction with 2,4-DNPH? (b)Which compound/s will test positive towards Baeyer’s test? (c)Which compound/s will produce a brick-red precipitate upon reaction with Fehling’s reagent (CuSO4, tartrate, NaOH)? (d)Which compound/s will test positive towards the Iodoform test?arrow_forward
- Chemarrow_forwardDetermine product (A) of the reaction (1) NK + DMF CH2 – Br (A) (81%) (2) HO¯/H2O (Benzyl bromide) (a) Ph – NH2 (c) Ph – CH2 – NH – CO,H (b) Ph – CH2 – NH2 (d) Ph – CH, - NH – CHOarrow_forwardWhat are the masses of the charged fragments produced in the following cleavage pathways? (a) Alpha cleavage of 2-pentanone (CH3COCH2CH2CH3) (b) Dehydration of cyclohexanol (hydroxycyclohexane) (c) McLafferty rearrangement of 4-methyl-2-pentanone [CH3COCH2CH(CH3)2] (d) Alpha cleavage of triethylamine [(CH3CH2)3N]arrow_forward
- (a) Provide a synthesis for the target molecule. All the carbons in your target must come from methyl acetate. H3C OCH3 methyl acetate Target (b) Provide a second synthesis of the same target that does not use LDA (iPr₂NLi) or an equivalent reagent.arrow_forwardAn unknown momosubstituted benzene was nitrated using a mixture of conc. HNO3 and H₂SO4. When the product was treated with the iodoform reagent, the reaction did not produce a yellow precipitate. The ¹H NMR spectrum of the nitrated product showed one singlet, one doublet and one triplet in the chemical shift region 7 - 7.8 ppm. Which structure is consistent with the given information? A B NO₂ I I only I and II only III only CH3 IV only NO₂ || OH CH3 NO₂ ||| OCH3 NO₂ IV 11arrow_forwardDraw a reaction mechanism for the reductive animation sequence. Highlight tautomers present in reactionarrow_forward
- STARTING WITH 18MG OF 2-methyl-2-butanol JUST B PLEASE (b) theoretical volume of alkene mixture (ml) expected to be obtained in this experiment.arrow_forwardHow are the following conversions carried out :(a) Aniline to p-hydroxyazobenzene(b) Ethanoyl chloride to Ethanenitrile.arrow_forwardThe reaction of 1- methylcyclopentene with mercuric trifluoroacetate in ethanol followed by reduction with sodium borohydride gives 1-ethoxy-1- methylcyclopentane. The -OH peak in the IR shows up at 1700 cm-1 as a sharp peak. (S)-2-bromohexane is the product of the reaction of (S)-2-hexanol with PBr3. The 1H NMR spectrum of 1- pentanol will show a peak for the H atom of the -OH group at 10 ppm delta. A tosylate is a great protecting group for an alcohol. The Williamson ether synthesis is an SN2 reaction of an alkoxide ion with a primary alkyl halide. Thionyl chloride converts ketones into alkyl halides. In an oxidation reaction, the oxygen content of our organic molecule decreases. ✓ [Choose ] False True [Choose ] [Choose ] [Choose ] [Choose ] [Choose ] [Choose ] [Choose ]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