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
Textbook Question
Chapter 10, Problem 10.39SP
Show how you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and any other necessary reagents.
- a. octan-3-ol from hexanal, CH3(CH2)4CHO
- b. octan-1-ol from 1-bromoheptane
- c. 1-cyclohexylethanol from acetaldehyde, CH3CHO
- d. 2-cyclohexylethanol from bromocyclohexane
- e. benzyl alcohol (Ph—CH2—OH) from bromobenzene (Ph—Br)
- f. cyclopentylphenylmethanol from benzaldehyde (Ph—CHO)
- g. octan-1-ol from 1-bromohexane
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Show the mecanism for the protection of the diol by forming an acetal with acetone. Remember this reaction occurs in an acidic environment
CH3 CH3 с H D CH,COCH; tocamobor CH3 Н.С. OH B 10 11
The following series of reactions yields ___________.
1) Butanoic acid and SOCl2; set product aside for use in step 3
2) Bromoethane in excess plus Mg and ether
3) Add the product of step 1 to the reaction mix of step 2
4) When the reaction is complete, add dilute aqueous acid
3-ethylhexan-3-ol
3-ethylheptan-2-ol
hexanoic acid
hexanal
3-heptanone
Show how you would synthesize the following:(a) 2-phenylethanol by the addition of formaldehyde to a suitable Grignard reagent(b) 2-phenylethanol from a suitable alkene(c) cyclohexylmethanol from an alkyl halide using an SN2 reaction(d) 3-cyclohexylpropan-1-ol by the addition of ethylene oxide to a suitable Grignard reagent(e) cis-pent-2-en-1-thiol from a suitable alkenyl halide(f) 2,5-dimethylhexane from a four-carbon alkyl halide
Chapter 10 Solutions
Organic Chemistry (9th Edition)
Ch. 10.3A - Prob. 10.1PCh. 10.3B - Give both the IUPAC name and the common name for...Ch. 10.3B - Prob. 10.3PCh. 10.3C - Give a systematic (IUPAC) name for each diol. a....Ch. 10.4B - Predict which member of each pair will be more...Ch. 10.4B - Dimethylamine (CH3)2NH, has a molecular weight of...Ch. 10.6A - Prob. 10.7PCh. 10.6A - Prob. 10.8PCh. 10.6C - A nitro group (NO2) effectively stabilizes a...Ch. 10.6C - Prob. 10.10P
Ch. 10.8B - Prob. 10.11PCh. 10.8B - Prob. 10.12PCh. 10.9A - Prob. 10.13PCh. 10.9B - Prob. 10.14PCh. 10.9C - Show how you would synthesize each tertiary...Ch. 10.9D - Prob. 10.16PCh. 10.9D - Show how you would add Grignard reagents to acid...Ch. 10.9D - A formate ester, such as ethyl formate, reacts...Ch. 10.9E - Prob. 10.19PCh. 10.9E - In Section9-7B, we saw how acetylide ions add to...Ch. 10.9F - Prob. 10.21PCh. 10.10A - Prob. 10.22PCh. 10.10B - Prob. 10.23PCh. 10.11B - Predict the products you would expect from the...Ch. 10.11B - Prob. 10.25PCh. 10.11B - Prob. 10.26PCh. 10.12 - Prob. 10.27PCh. 10.12 - Prob. 10.28PCh. 10.12 - Authentic skunk spray has become valuable for use...Ch. 10 - Give a systematic (IUPAC) name for each alcohol....Ch. 10 - Give systematic (IUPAC) names for the following...Ch. 10 - Draw the structures of the following compounds...Ch. 10 - Predict which member of each pair has the higher...Ch. 10 - Predict which member of each pair is more acidic,...Ch. 10 - Predict which member of each group is most soluble...Ch. 10 - Draw the organic products you would expect to...Ch. 10 - Prob. 10.37SPCh. 10 - Show how you would synthesize the following...Ch. 10 - Show how you would use Grignard syntheses to...Ch. 10 - Show how you would accomplish the following...Ch. 10 - Show how you would synthesize the following: a....Ch. 10 - Complete the following acid-base reactions. In...Ch. 10 - Prob. 10.43SPCh. 10 - Prob. 10.44SPCh. 10 - Geminal diols, or 1,1-diols, are usually unstable,...Ch. 10 - Vinyl alcohols are generally unstable, quickly...Ch. 10 - Compound A (C7H11Br) is treated with magnesium in...Ch. 10 - Prob. 10.48SPCh. 10 - Prob. 10.49SPCh. 10 - Prob. 10.50SPCh. 10 - Prob. 10.51SPCh. 10 - Prob. 10.52SPCh. 10 - Prob. 10.53SPCh. 10 - Prob. 10.54SPCh. 10 - Prob. 10.55SPCh. 10 - Prob. 10.56SPCh. 10 - Show how this 1 alcohol can be made from the...Ch. 10 - Prob. 10.58SPCh. 10 - Prob. 10.59SPCh. 10 - Prob. 10.60SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
How could you separate a mixture of the following compounds? The reagents available to you are water, either, 1...
Organic Chemistry
Practice Problem 1.22 Which of the following alkenes can exist as cis-trans isomers? Write their structures. Bu...
Organic Chemistry
During the early part of the 20th century, sulfanilamide (an antibacterial drug) was only administered by injec...
Elementary Principles of Chemical Processes, Binder Ready Version
141. Design a device that uses as electrochemical cell to determine amount of
in a sample water Describe, in...
Chemistry: Structure and Properties (2nd Edition)
What is the pH range for acidic solutions? For basic solutions?
EBK INTRODUCTION TO CHEMISTRY
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
- Show you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and anyother necessary reagents. 2-cyclohexylethanol from bromocyclohexanearrow_forwardShow how you would synthesis the chloride, bromide, and iodide from the corresponding alcohols. (a) 1-halopentane (halo-chloro, bromo, iodo) (b) halocyclobutane (c) 1-halo-1-ethylcyclopentane (d) 1-halo-2-propylcyclopentanearrow_forwardCompounds A, B, and C which are all alcohols are subjected to the Lucas test. An oily layer was formed almost instantly after the addition of reagents to Compound C. For compound A, it took several minutes before an oily layer was formed. Meanwhile, it took at least one hour with compound B before an oily layer was observed. What could be compound B? Choices: Ethanol Isopropyl alcohol tert-butyl alcoholarrow_forward
- Show you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and anyother necessary reagents. 1-cyclohexylethanol from acetaldehyde, CH3CHOarrow_forwardChoose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) KMnO4, H3O+ CH3Cl, AlCl3 HNO3, H2SO4 Cl2, FeCl3 fuming sulfuric acidarrow_forwardStarting from cyclohexanol, show how to prepare: Show all reagents and molecules synthesized along the way after each step. You do not have to use curved arrows.arrow_forward
- Show how you would prepare cyclopentene from each compound.(a) cyclopentanol(b) cyclopentyl bromide(c) cyclopentane (not by dehydrogenation)arrow_forwardHow would you prepare the following ethers? Use whichever method you think is more appropriate, Williamson synthesis or the alkoxymercuration reaction. (a) Butyl cyclohexyl ether (b) Benzyl ethyl ether (C6H5CH2OCH2CH3) (c) sec-Butyl tert-butyl ether (d) Tetrahydrofuranarrow_forwardShow you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and anyother necessary reagents.(a) octan-3-ol from hexanal, CH3(CH2)4CHOarrow_forward
- 1. (a) Oxidation of 1-butanol with PCC will produce which of the following? 2-chlorobutanal butanone butanoic acid butanal (b) Which synthetic route is the best way to prepare ethyl isopropyl ether? CH3CH2OH + (CH3)2CHOH + H2SO4, 140 oC CH3CH2ONa + (CH3)2CHOH CH3CH2ONa + (CH3)2CHBr (CH3)2CHONa + CH3CH2Br (c) The Williamson ether synthesis involves nucleophilic substitution involving an alkyl halide and an alcohol. (True or False)arrow_forwardWhat are the reagents used in each case below.arrow_forwardDraw the structure of the two ketones which may be used to make the tertiary alcohol shown below by reaction with a Grignard reagent.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY