EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
9th Edition
ISBN: 9781305084391
Author: McMurry
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Question
Chapter 17.SE, Problem 77AP
Interpretation Introduction
Interpretation:
The reaction of sodium phenoxide with iodomethane yields anisole. What kind of reaction is taking place in this conversion is to be stated. A mechanism for the conversion is to be proposed.
Concept introduction:
Phenoxide ion is nucleophilic. When it is treated with alkyl iodides a bimolecular nucleophilic displacement (SN2) reaction will occur. Iodine is removed and phenoxy group gets attached to methyl group.
To state:
The kind of reaction that occurs when phenoxide ion is treated with iodomethane to produce anisole is to be stated. A mechanism for this reaction is also to be proposed.
To propose:
A mechanism for this conversion.
Expert Solution & Answer

Trending nowThis is a popular solution!

Students have asked these similar questions
Consider the following SN 2 reaction:
مار
+
Br
H₂O
acetone
+ Br
OH
What effect would each of the following changes have on the rate of this reaction. Select the single best answer for each part.
Part 1 of 3
If the substrate was changed to:
The rate would
Br
O increase
O decrease
O remain unchanged
Part 2 of 3
×
S
If the nucleophile was changed to OH, the rate would:
O increase
O decrease
O remain unchanged
Part 3 of 3
If the solvent was changed to ethanol, the rate would:
Increase
O decrease
O remain unchanged
2
ol
Ar
Consider the following nucleophilic substitution reaction. The compound listed above the arrow is the solvent for the reaction. If nothing is listed over the arrow,
then the nucleophile is also the solvent for the reaction.
Part: 0/2
Part 1 of 2
Br
acetone
+ I
What is the correct mechanism for the reaction? Select the single best answer.
OSN 1
OSN 2
X
Part: 1/2
Part 2 of 2
Draw the products for the reaction. Include both the major organic product and the inorganic product. If more than one stereoisomer is possible, draw
only one stereoisomer. Include stereochemistry where relevant.
Click and drag to start drawing a
structure.
Х
5
☐
Triethyloxonium tetrafluoroborate reacts with ethanol (CH3CH2OH) to give diethyl ether (CH3CH2OCH2CH3).
BF
triethyloxonium tetrafluoroborate
Which equation, including the curved arrows, best represents the rate-determining step in the mechanism? Select the single best answer.
O
OH
CH3CH2
OH
+
H.
0+
CH₂H₂
:0
+
0+
ж
+
H
+
:0:
0
C
Chapter 17 Solutions
EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2PCh. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5PCh. 17.3 - Prob. 6PCh. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8PCh. 17.5 - Prob. 9PCh. 17.5 - Prob. 10P
Ch. 17.5 - Use the reaction of a Grignard reagent with a...Ch. 17.6 - How would you carry out the following...Ch. 17.6 - What products(s) would you expect from dehydration...Ch. 17.7 - What alcohols would give the following products on...Ch. 17.7 - What products would you expect from oxidation of...Ch. 17.8 - TMS ethers can be removed by treatment with...Ch. 17.9 - Show the mechanism for the reaction of...Ch. 17.11 - Prob. 18PCh. 17.11 - When the 1HNMR spectrum of an alcohol is run in...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw the structure of the carbonyl compound(s)...Ch. 17.SE - Prob. 22VCCh. 17.SE - Prob. 23VCCh. 17.SE - Name and assign R or S stereochemistry to the...Ch. 17.SE - Evidence for the intermediate carbocations in the...Ch. 17.SE - Acid-catalyzed dehydration of 2,...Ch. 17.SE - Prob. 27MPCh. 17.SE - Treatment of the following epoxide with aqueous...Ch. 17.SE - Prob. 29MPCh. 17.SE - Prob. 30MPCh. 17.SE - Identify the type of substitution mechanism (SN1,...Ch. 17.SE - The conversion of 3 alcohols into alkenes under...Ch. 17.SE - Prob. 33MPCh. 17.SE - The trimethylsilyl (TMS) protecting group is one...Ch. 17.SE - When the alcohol below is treated with POCI3 and...Ch. 17.SE - Phenols generally have lower pKa’s than...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw and name the eight isomeric alcohols with...Ch. 17.SE - Prob. 39APCh. 17.SE - Named bombykol, the sex pheromone secreted by the...Ch. 17.SE - Carvacrol is a naturally occurring substance...Ch. 17.SE - What Grignard reagent and what carbonyl compound...Ch. 17.SE - What carbonyl compounds would you reduce to...Ch. 17.SE - What carbonyl compounds might you start with to...Ch. 17.SE - Prob. 45APCh. 17.SE - What products would you obtain from reaction of...Ch. 17.SE - Prob. 47APCh. 17.SE - How would you prepare the following compounds from...Ch. 17.SE - Prob. 49APCh. 17.SE - What products would you expect to obtain from...Ch. 17.SE - Prob. 51APCh. 17.SE - Propose structures for alcohols that have the...Ch. 17.SE - Propose a structure consistent with the following...Ch. 17.SE - The 1HNMR spectrum shown is that of...Ch. 17.SE - A compound of unknown structure gave the following...Ch. 17.SE - Propose a structure for a compound C15H24O that...Ch. 17.SE - Prob. 57APCh. 17.SE - Prob. 58APCh. 17.SE - Rank the following substituted phenols in order of...Ch. 17.SE - Benzvl chloride can be converted into benzaldehvde...Ch. 17.SE - Prob. 61APCh. 17.SE - Prob. 62APCh. 17.SE - Prob. 63APCh. 17.SE - Prob. 64APCh. 17.SE - Prob. 65APCh. 17.SE - Prob. 66APCh. 17.SE - Dehydration of trans-2-methylcyclopentanol with...Ch. 17.SE - 2, 3-Dimethyl-2, 3-butanediol has the common name...Ch. 17.SE - As a rule, axial alcohols oxidize somewhat faster...Ch. 17.SE - Prob. 70APCh. 17.SE - A problem often encountered in the oxidation of...Ch. 17.SE - Identify the reagents a-f in the Following scheme:Ch. 17.SE - Prob. 73APCh. 17.SE - Prob. 74APCh. 17.SE - Compound A, C8H10O, has the IR and 1H NMR spectra...Ch. 17.SE - Prob. 76APCh. 17.SE - Prob. 77AP
Knowledge Booster
Similar questions
- CH3CH2CH=CH2 + H₂O − H+arrow_forwardГ C-RSA CHROMATOPAC CH=1 DATA 1: @CHRM1.C00 ATTEN=10 SPEED= 10.0 0.0 b.092 0.797 1.088 1.813 C-RSA CHROMATOPAC CH=1 Report No. =13 ** CALCULATION REPORT ** DATA=1: @CHRM1.000 11/03/05 08:09:52 CH PKNO TIME 1 2 0.797 3 1.088 4 1.813 AREA 1508566 4625442 2180060 HEIGHT 207739 701206 V 287554 V MK IDNO CONC NAME 18.1447 55.6339 26.2213 TOTAL 8314067 1196500 100 C-R8A CHROMATOPAC CH=1 DATA 1: @CHRM1.C00 ATTEN=10 SPEED= 10.0 0. 0 087 337. 0.841 1.150 C-R8A CHROMATOPAC CH=1 Report No. =14 DATA=1: @CHRM1.000 11/03/05 08:12:40 ** CALCULATION REPORT ** CH PKNO TIME AREA 1 3 0.841 1099933 41.15 4039778 HEIGHT MK IDNO 170372 649997¯¯¯ CONC NAME 21.4007 78.5993 TOTAL 5139711 820369 100 3 C-R8A CHROMATOPAC CH=1 DATA 1: @CHRM1.C00 ATTEN=10 SPEED= 10.0 0.100 0:652 5.856 3 1.165 C-RSA CHROMATOPAC CH-1 Report No. =15 DATA=1: @CHRM1.000 11/03/05 08:15:26 ** CALCULATION REPORT ** CH PKNO TIME AREA HEIGHT MK IDNO CONC NAME 1 3 3 0.856 4 1.165 TOTAL 1253386 4838738 175481 708024 V 20.5739 79.4261 6092124…arrow_forwardIndicate the product that is obtained if the benzotriazole reacts with the use of a medium basic product.arrow_forward
- Indicate the product that is obtained if the benzotriazol reacts with dimethyl sulfate.arrow_forwardIndicate how to obtain 2-metilbencimidazol from 1,2-diaminobenzene.arrow_forwardbreak down both reactions shown and explain it correctly using the bromonium ion mechanism, instead of the (disproven) carbocation-based mechanism.arrow_forward
- Indicate how from 1,2-diaminobenzene to obtain 1-metilbenzotriazol.arrow_forward-C = C - C - + Br₂ + I" -> -C-C-c -C = C -C- + Br² + I₂ -C=C Br I + Brū + Iz -7- C - C-C- I Br Mechanism; - C = c - c - + Br - Br > - C-c-c- Br -C-C-C- + 1 - - -Ċ-Ċ'-c' - Br Br Iarrow_forwardWrite the mechanism of the esterification reaction (please show the mechanism included line pairs and arrows)arrow_forward
- How do I break down the reaction shown on the chalkboard and explain it correctly using the bromonium ion mechanism, instead of the (disproven) carbocation-based mechanismarrow_forward¿Qué the product is obtained from tetraethoxypropano and hidrazina?. Indicate the reason why the corresponding dial is used.arrow_forwardIf CH3COCH2CH(OCH3)2 is reacted with hydrazine, two isomeric products are formed. Indicate their structures and the major product.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