ORGANIC CHEMISTRY-PACKAGE
8th Edition
ISBN: 9780134647586
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 11, Problem 40P
A student added an equivalent of 3,4-epoxy-4-methykyclohexanol to a solution of methylmagnesium bromide in diethyl ether, and then added dilute hydrochloric acid. He expected that the product would be 1,2-dimethyl-1,4-yclohexanodiol. He did not get any of the expected product. What product did he get?
3,4-epoxy-4-methyl-cyclohexanol
1,2-dlmethyl-1,4-cydohexanediol
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Show how the following compounds can be synthesized from benzene:
a. N,N,N-trimethylanilinium iodide b. 2-methyl-4-nitrophenol c. p-benzylchlorobenzene d. benzyl methyl ether e. p-nitroaniline f. m-bromoiodobenzene g. p-dideuteriobenzene h. p-nitro-N-methylaniline i. 1-bromo-3-nitrobenzene
How many stereoisomers are obtained from the reaction of 3-methyl-2-butanone with each of the following organometallic reagents followed by the addition of dilute acid? Name each stereoisomer.
ethyllithium
methylmagnesium bromide
Show the products from the reaction of p-bromoaniline with following reagents:
a)CH3Cl(excess)
b) HCl
c) CH3COCl
d) CH3MgBr
e) CH3CH2Cl, AlCl3
Chapter 11 Solutions
ORGANIC CHEMISTRY-PACKAGE
Ch. 11.1 - Prob. 1PCh. 11.2 - Which is more reactive an organolithium compound...Ch. 11.2 - Prob. 3PCh. 11.3 - Muscalure is the sex attractant of the common...Ch. 11.3 - Prob. 7PCh. 11.3 - Prob. 8PCh. 11.3 - Prob. 9PCh. 11.3 - Prob. 10PCh. 11.4 - Prob. 13PCh. 11.4 - Prob. 14P
Ch. 11.4 - Prob. 15PCh. 11.4 - Prob. 16PCh. 11.4 - Prob. 17PCh. 11.4 - Prob. 19PCh. 11.4 - Show how the Suzuki and/or Heck reactions can be...Ch. 11.4 - Identify two pairs of an alkyl bromide and an...Ch. 11.5 - Prob. 22PCh. 11.5 - Draw the product of ring-closing metathesis for...Ch. 11.5 - Prob. 25PCh. 11.5 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - The coupling of an alkyne with an aryl halide in...Ch. 11 - Identify A through H.Ch. 11 - Using the given starting material, any necessary...Ch. 11 - What alkyl halide reacts with lithium...Ch. 11 - Prob. 33PCh. 11 - Prob. 34PCh. 11 - The following compound undergoes an intramolecular...Ch. 11 - Using ethynyleyclohexane as a starting material...Ch. 11 - Prob. 37PCh. 11 - Using the given starting material, any necessary...Ch. 11 - Prob. 39PCh. 11 - A student added an equivalent of...Ch. 11 - Using the given starting material, any necessary...Ch. 11 - Prob. 42PCh. 11 - Prob. 43PCh. 11 - Bombykol is the sex pheromone of the silk moth....Ch. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - A dibromide loses only one bromine when it reacts...Ch. 11 - What starting material is required in order to...Ch. 11 - What product is obtained from ring-opening...
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
- 2-Bromo-6, 6-dimethylcyclohexanone gives 2, 2-dimethylcyclopentane- carboxylic acid on treatment with aqueous NaOH followed by acidification, a process called the Favorskii reaction. Propose a mechanism.arrow_forwardWhat stereoisomers are formed in the following reactions? Which stereoisomer is the major product? a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexenearrow_forwardPredict the mononitration products of the following compounds.(a) o-nitrotoluene (b) m-chlorotoluene(c) o-bromobenzoic acid (d) p-methoxybenzoic acid(e) m-cresol (m-methylphenol) (f) o-hydroxyacetophenonearrow_forward
- Which of the following starting materials and reagents would be best to produce a racemic mixture of 3-methyl-3-hexanol? a. heptanone and 1. CH3MgBr 2. H3O+ b. hexanal and 1. CH3MgBr, 2. H3O+ c. 3-hexanone and 1. CH3MgBr, 2. H3O+ d. butanal and 1. CH3CH2MgBr, 2. H3O+arrow_forwardWhat is the product resulted due to the reaction of 2-hydroxy-3-methoxybenzaldehyde with ethyl bromoacetate in a basic solution indicating all the reagents and intermediates occurred during the reaction? What is the product obtained when product A reacted with ethyl acetate in the same basic solution?arrow_forwardWhich of the following compounds would be used to prepare the alkene shown below by the Wittig reaction? A. cyclohexyl bromide/propanal B. cyclohexanone/ethyl bromide C. cyclohexyl bromide/isopropyl bromide D. cyclohexanone/ethanalarrow_forward
- How would you prepare the following compounds from 2- phenylethanol? More than one step may be required. a. Styrene (PhCH=CH2) b. Phenylacetaldehyde (PhCH2CHO) c. Phenylacetic acid (PhCH2CO2H) d. Benzoic acid e. Ethylbenzene f. Benzaldehyde g. 1-Phenylethanol h. 1-Bromo-2-phenylethanearrow_forwardWhat condensation products would you expect to obtain by treatment of the following substance with sodium ethoxide in ethanol? (a) Trimethylacetaldehyde (b) Cyclobutanone(c) Benzophenone (diphenyl Ketone) (d) 3-pentanone(e)Decanel (f) 3-phenyl-2propenalarrow_forwardWhat is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents? a. 0.1 M HCl b. CH3OH/HCl c. 0.1 M NaOH d. CH3OH/CH3O-arrow_forward
- What is the best set of reagents to achieve deoxygenation of 2-pentanone to pentane? A. NaClO2/NaH2PO4 B. LiAlH4, Et2O C. DIBAL-H, THF D. NH2NH2/t-BuOK, DMSOarrow_forwardA step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forward
arrow_back_ios
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
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License