Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 11, Problem 13PP
Interpretation Introduction
Interpretation:
Reaction mechanism for the reactions (a) and (b) are to be written. Explanation of no
Concept introduction:
If a proton is removed from the hydroxyl group, the result obtained is an alkoxide ion.
The alkoxide ion reacts further with itself in an intramolecular manner via a
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Practice Problem 13.36b
Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the
following epoxide from acetylene:
H"
'Et
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters
(without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer.
A
B
C
D
DMP or PCC
На, Pt
EtBr
PHCH2BR
E
F
H
H2SO4, H20, HgSO4
МСРВА (RCO3зН)
Na, NH3 (/)
H2, Lindlar's cat.
I
K
TSCI, py
PhBr
NANH2
1) EtMgBr; 2) H30+
Propose suitable reagents to accomplish the following transformations.
Draw a structural formula for the alcohol formed by treating each alkene with borane
in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide,
and specify stereochemistry where appropriate.
(a)
(d)
(b)
(e)
(c)
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - PRACTICE PROBLEM
11.8 Show how you would prepare...Ch. 11 - PRACTICE PROBLEM
11.9 Write structures for...Ch. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - 11.33 What compounds would you expect to be formed...Ch. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - 11.37 Outlined below is a synthesis of the gypsy...Ch. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Prob. 40PCh. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 43PCh. 11 - 11.44 Write a mechanism that accounts for the...Ch. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 56PCh. 11 - Prob. 57PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...Ch. 11 - 11.1 Which set of reagents would effect the...Ch. 11 - Prob. 2QCh. 11 - 11.3 The following compounds have identical...Ch. 11 - Complete the following synthesis:Ch. 11 - Two configurations can actually be envisioned for...
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- PRACTICE PROBLEM 8.20 Specify the alkene and reagents needed to synthesize each of the following diols. OH HO- (a) (b) (c) HO. н он HO (racemic) (racemic)arrow_forward(a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEtarrow_forward(b) A student wanted to synthesize methyl tert-butyl ether. He attempted the synthesis by adding sodium methoxide to tert-butyl chloride, but he obtained none of the desired product (1) (ii) Use an equation to show the product formed in this reaction Propose a suitable William ether synthetic route for methyl tert-butyl ether tach l.arrow_forward
- Predict the major products of the following reactions, including stereochemistry where appropriate. (a) potassium tert-butoxide + methyl iodide (b) sodium methoxide + tert-butyl iodidearrow_forward8.30 Outline an efficient synthesis of each of the following compounds from the indicated start- ing material and any necessary organic or inorganic reagents: (a) Cyclopentyl cyanide from cyclopentane (b) Cyclopentyl cyanide from cyclopentene (c) Cyclopentyl cyanide from cyclopentanol (d) NCCH₂CH₂CN from ethyl alcohol (e) Isobutyl iodide from isobutyl chloride (f) Isobutyl iodide from tert-butyl chloride (g) Isopropyl azide from isopropyl alcohol (h) Isopropyl azide from 1-propanol (i) (S)-sec-Butyl azide from (R)-sec-butyl alcohol (i) (S)-CH3CH₂CHCH3 from (R)-sec-butyl alcohol SHarrow_forwardExplain the following observations :(i) The boiling point of ethanol is higher than that of methoxymethane.(ii) Phenol is more acidic than ethanol.(iii) o- and p-nitrophenols are more acidic than phenol.arrow_forward
- Write structural formulas for the cyclohexadienyl cations formed from aniline (C6H5NH2) during(a) Ortho bromination (four resonance structures)(b) Meta bromination (three resonance structures)(c) Para bromination (four resonance structures)arrow_forward11:43 Q1. (a) (c) (d) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Library Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂ Name of mechanism Mechanism (ii) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Select Name Stereoisomer 2 When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH Br Page 2 of 14 CH3 H3C-C-CH3 + KBr ОН State the role of the hydroxide ions in this reaction. Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product 9,284 Photos, 1,166 Videos For You…arrow_forward(c) Answer each of the questions below that relate to acetophenone: Xo (i) (ii) (iii) Draw the structure of the enol form of acetophenone. Give a stepwise mechanism for the conversion of acetophenone into its enol form. Show how each of the three compounds A, B and C below can be prepared from acetophenone. Explain clearly what reactants/reagents would be required in each case. odocor A B Br Carrow_forward
- Guiding your reasoning by retrosynthetic analysis, show how you could prepare each of the following compounds from the given starting material and any necessary organic or inorganic reagents. All require more than one synthetic step. (a) Cyclopentyl iodide from cyclopentane (b) 1-Bromo-2-methylpropane from 2-bromo-2-methylpropane (c) meso-2,3-Dibromobutane from 2-butyne (d) 1-Heptene from 1-bromopentane (e) cis-2-Hexene from 1,2-dibromopentane (f) Butyl methyl ether (CH3CH2CH2CH2OCH3) from 1-butenearrow_forwardSolve A through Carrow_forwardPlease help with (a) and (b)arrow_forward
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