Concept explainers
(a)
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:
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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Chapter 7 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
- 1. (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_forwardWhich 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_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_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_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_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_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_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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