Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 7.9, Problem 7.6P
(a)
Interpretation Introduction
Interpretation:
1-Heptanol is synthesised using given synthetic scheme has to be shown.
Concept introduction:
The Lindlar catalyst is a deactivated hydrogenation catalyst that stops alkyne hydrogenation at the alkene stage, allowing conversion of
Hydroboration–protonolysis is an alternative way to prepare a cis-alkene from an alkyne.
(b)
Interpretation Introduction
Interpretation:
2-Heptanol is synthesised using given synthetic scheme has to be shown.
Concept introduction:
The Lindlar catalyst is a deactivated hydrogenation catalyst that stops alkyne hydrogenation at the alkene stage, allowing conversion of alkynes to cis-alkenes. Hydroboration followed by an acid workup (instead of basic peroxide) also gives cis-alkenes from alkynes. Hydroboration–protonolysis is an alternative way to prepare a cis-alkene from an alkyne.
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6. Describe concisely a chemical test to distinguish between the following pairs of
compounds.
Terangkan secara ringkas ujian kimia bagi membezakan pasangan sebatian
berikut.
(a) Propanal and propanone
(b) Phenol and benzoic acid
(c)
Hexan-3-one and hexan-2-one
(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enal
Explain the following statements. You must use chemical equations to justify your
explanation.
(ii)
(I)
Phenol is more acidic than cyclohexanol.
Chapter 7 Solutions
Organic Chemistry
Ch. 7.2 - Write the IUPAC name of each compound.Ch. 7.2 - Write the common name of each alkyne.Ch. 7.5 - Prob. 7.3PCh. 7.7 - Draw a structural formula for a hydrocarbon with...Ch. 7.7 - Hydration of 2-pentyne gives a mixture of two...Ch. 7.9 - Prob. 7.6PCh. 7 - Prob. 7.7PCh. 7 - Show how to prepare each alkyne from the given...Ch. 7 - Prob. 7.9PCh. 7 - Complete each acid-base reaction and predict...
Ch. 7 - Draw structural formulas for the major product(s)...Ch. 7 - Draw the structural formula of the enol formed in...Ch. 7 - Prob. 7.13PCh. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Show reagents and experimental conditions you...Ch. 7 - Show reagents and experimental conditions you...Ch. 7 - Show how to convert 1-butyne to each of these...Ch. 7 - Prob. 7.19PCh. 7 - Show reagents and experimental conditions to bring...Ch. 7 - Show reagents to bring about each conversion.Ch. 7 - Propose a synthesis for (Z)-9-tricosene...Ch. 7 - Propose a synthesis of each compound starting from...Ch. 7 - Show how to prepare each compound from 1-heptene....Ch. 7 - Prob. 7.25PCh. 7 - Prob. 7.26PCh. 7 - Following is the structural formula of the...Ch. 7 - The standard procedure for synthesizing a compound...Ch. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Prob. 7.35P
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- Which is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forward1. (a) Indene is considered much acidic compare to most hydrocarbons. It is readily reacting with strong base such as NaNH2 to form its conjugate base. + NANH2 + NH3 Nat indene (i) Draw the conjugate base of indene. (ii) Explain why indene is much acidic compare to most hydrocarbons.arrow_forward(a) One test for the presence of an alkene is to add a smallamount of bromine, which is a red-brown liquid, and lookfor the disappearance of the red-brown color. This test doesnot work for detecting the presence of an aromatic hydrocarbon.Explain. (b) Write a series of reactions leading topara-bromoethylbenzene, beginning with benzene andusing other reagents as needed. What isomeric side productsmight also be formed?arrow_forward
- Acid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2-methyl-2-heptene as shown in the following equation.(a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the flow of electrons. (b) What other alkenes do you think are formed in this reaction?arrow_forward(a) Which of the following will NOT produce a carboxylic acid or carboxylate ion? 1-butanol + H2CrO4 2-butene + O3/H2O2 butanal + PCC butanal + H2CrO4 (b) Which of the following will NOT produce a carboxylic acid or carboxylate ion? 1-butanol + H2CrO4 2-butene + O3/H2O2 butanal + PCC butanal + H2CrO4arrow_forwardDevelop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentanearrow_forward
- Answer ALL parts of this question. (a) Using resonance structures, discuss the following statement; phenols are much stronger acids than aliphatic alcohols. (b) Give the structure of a stronger organic acid than phenol. (c) Rationalise the acidity of the latter organic acid by drawing two resonance structures of the conjugate base. (d) Eugenol is a natural product derived from the dried flower buds of the evergreen tree, Eugenia aromatica. Briefly describe a procedure with reagents required to extract eugenol as a single component from the mixture of compounds present in these flower buds. OH LOCH 3 eugenolarrow_forwardThe hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?arrow_forwardWhat will be the color of the flame and the amount of soot if the following are ignited:(a) Hexane (b)Heptane(c) Cyclohexane (d) Cyclohexene (e) Benzene (f) Toluenearrow_forward
- Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)(b) cis-1-ethyl-2-methylcyclopropanearrow_forward3. (a) Draw the structure of 1-ethylcyclohexene (B). (b) Draw the structures of the two possible products that can result from treating B with hydrogen bromide and very briefly explain which one will be favoured). (c) Draw the curly arrow mechanism for the formation of the favoured productarrow_forwardDescribe how would you distinguish the following pairs, (a) Benzene and cyclohexane (b) Phenol and toluene (c) Phenol and benzoic acidarrow_forward
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