Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 12, Problem 9PP
Practice Problem 12.7
Provide retrosynthetic analyses and syntheses for each of the following alcohols, starting with appropriate alkyl or aryl halides.
(a)
(b)
(c)
(d)
(e)
(f)
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Students have asked these similar questions
(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
C
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.
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 3PPCh. 12 - PRACTICE PROBLEM Assign oxidation states to each...Ch. 12 - Prob. 2PPCh. 12 - PRACTICE PROBLEM
12.4 What oxidation product would...Ch. 12 - Prob. 5PPCh. 12 - PRACTICE PROBLEM 12.4 Predict the products of the...Ch. 12 - Prob. 7PPCh. 12 - Prob. 8PPCh. 12 - Practice Problem 12.7
Provide retrosynthetic...Ch. 12 - Prob. 10PP
Ch. 12 - What products would you expect from the reaction...Ch. 12 - What products would you expect from the reaction...Ch. 12 - What product (or products) would be formed from...Ch. 12 - Prob. 14PCh. 12 - 12.13 Write reaction conditions and the product...Ch. 12 - Prob. 16PCh. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the major organic product from each of the...Ch. 12 - 12.21 Predict the major organic product from each...Ch. 12 - 12.22 Predict the product of the following...Ch. 12 - Synthesize each of the following compounds from...Ch. 12 - Prob. 24PCh. 12 - 21. Write a mechanism for the following reaction....Ch. 12 - Prob. 26PCh. 12 - Prob. 27PCh. 12 - 23. What organic products A-H would you expect...Ch. 12 - Prob. 29PCh. 12 - Show how 1-pentanol could be transformed into each...Ch. 12 - Provide the reagents needed to accomplish...Ch. 12 - Prob. 32PCh. 12 - For each of the following alcohols, write a...Ch. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - 34. Synthesize the following compound using...Ch. 12 - 37. Explain how and IR spectroscopy could be used...Ch. 12 - 12.40
When sucrose (common table sugar) is treated...Ch. 12 - 38. An unknown X shows a broad absorption band in...Ch. 12 - Prob. 1LGPCh. 12 - Which of the following could be employed to...Ch. 12 - Prob. 2QCh. 12 - 12.3 Supply the missing reagents.
Ch. 12 - 12.4 Supply the missing reagents and...Ch. 12 - Supply the missing starting compound.
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- Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)arrow_forwardSuggest the most appropriate method for each of the following laboratory syntheses.(a) cyclopentanol ¡ cyclopentanonearrow_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
- Describe the characteristic infrared absorption frequencies that would allow you to distinguish between the following pairs of compounds. (a) cyclohex-2-enone and cyclohex-3-enone (b) cyclohexanol and cyclohexanonearrow_forwardShow reagents to bring about each conversion. (c) Br (d) (b) (а) (e) (f) H.arrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forward
- 5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanolarrow_forwardGuiding 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_forwardWrite 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_forward
- 8. (a) Benzene derivatives exhibit medium to strong absorption in UV-region. Explain why aniline and phenoxide ion have strong UV-absorptions.arrow_forwardPredict the major organic product of each of the following reactions or provide the reagent needed to complete each transformation.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
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