Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 15, Problem 14PP
Interpretation Introduction
Interpretation:
The major product formed in each of the given reactions is to be identified.
Concept introduction:
The oxymercuration-demercuration reaction of alkenes leads to the formation of alcohol according to Markovnikov’s addition.
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Starting exactly with any acid chloride with exactly with 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules:
(a) 2,6-dimethyl-4-heptanone
(b) 4-propyl-4-octanol
Provide the reagents required to complete the following transformations.
(a)
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(b)
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11:43
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
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Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - PRACTICE PROBLEM
15.6 Explain how the percentages...Ch. 15 - PRACTICE PROBLEM
15.7
Predict the major products...Ch. 15 - Prob. 8PPCh. 15 - Prob. 9PPCh. 15 - Prob. 10PP
Ch. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM
15.16 Predict the major product...Ch. 15 - PRACTICE PROBLEM Account for the following...Ch. 15 - PRACTICE PROBLEM 1-Chloro-3-methyl-2-butene...Ch. 15 - Prob. 19PPCh. 15 - PRACTICE PROBLEM
15.20 The following chlorides (Ph...Ch. 15 - Prob. 21PPCh. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 24PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Predict the major product (or products) formed...Ch. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Predict the major products of the following...Ch. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Starting with aniline, outline a synthesis of each...Ch. 15 - Prob. 36PCh. 15 - 15.37 Propose structures for compounds G–I:
Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Show how you might synthesize each of the...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Treating cyclohexene with acetyl chloride and...Ch. 15 - 15.47 The tert-butyl group can be used as a...Ch. 15 - When toluene is sulfonated (concentrated H2SO4) at...Ch. 15 - Prob. 49PCh. 15 - 15.50 Heating 1,1,1-triphenylmethanol with ethanol...Ch. 15 - 15.51
(a) Which of the following halides would you...Ch. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 54PCh. 15 - When compound C, which is often used to model a...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...Ch. 15 - Which of the following compounds would be most...Ch. 15 - 15.2 Which of the following is not a...Ch. 15 - Prob. 3QCh. 15 - Complete the following syntheses.
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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
- The following compound, 2-hydroxycycloheptatrienone, does not give all the usual carbonyl group reactions. (i) Explain this apparent anomaly. Furthermore, explain the significant difference between the relative stability of this compound and its 3- and 4-hydroxy isomers. (ii) What would you expect to be the influence of adding (a) a nitro group as a substituent on the 7-membered ring or (b) an alkyl group, on the degree of aromaticity of the above compound. (iii) Based on your understanding of the hydrogen bonding concept, which isomer would you expect to have a higher m.p, (assuming they are both solids) between 2- and 4- hydroxycycloheptatrienone? Explain your choice.arrow_forwardRank the compounds in each group according to their reactivity towardelectrophilic substitution.(a) Chlorobenzene, o-dichlorobenzene, benzene(b) p-Bromonitrobenzene , nitrobenzene, phenol(c) Fluorobenzene, benzaldehyde, a-xylene(d) Benzonitrile, p-methylbenzonitr ile,p-methoxybenzonitrilearrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forward
- Suggest readily available starting materials and reaction conditions suitable for obtaining each of the following compounds by a procedure involving alkylation of nucleophilic carbon. (a) PHCH2CH2CHPH (b) (CH3)½C=CHCH2CH2CCH2CO;CH3 ČN (c) (d) CH2=CHCH=CHCH2CH2CO,H CH3 CH2CO2H CH3 CH3CO CH;CH2CH2 (f) (e) 2,3-diphenylpropanoic acid (g) CH3Oʻ CH3CH2 CH2CH=CH2arrow_forwardPredict the major organic product of each of the following reactions or provide the reagent needed to complete each transformation.arrow_forwardProvide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)arrow_forward
- Explain 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_forwardGive reasons :(a) n-Butyl bromide has higher boiling point than f-butyl bromide.(b) Racemic mixture is optically inactive.(c) The presence of nitro group (-NO2) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions.arrow_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
- (a) Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-epoxyhexane)and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, payparticular attention to the stereochemistry of the intermediates and products.(b) Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- andtrans-hex-3-ene. Is this reaction sequence stereospecific?arrow_forwardPropose suitable reagents to accomplish the following transformations.arrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward
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