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(a)
Interpretation:
Both the chair conformations for cis-1,2-dimethylcyclohexane is to be drawn and the compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents are to be determined.
Concept Introduction:
The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
(b)
Interpretation:Both the chair conformations for trans-1,2-dimethylcyclohexane is to be drawn and should identify the compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents.
Concept Introduction:The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
(c)
Interpretation:Both the chair conformations for cis-1,3-dimethylcyclohexane are to be drawn and the compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents are to be determined.
Concept Introduction:The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
(d)
Interpretation:Both the chair conformations for trans-1,3-dimethylcyclohexane are to be drawn andthe compounds (compared with other given compounds) having equal numbers of axial and equatorial substituents are to be determined.
Concept Introduction:The isomers are drawn on the basis of cis and trans-positions of the given compound, also in certain conformations, C-H bonds exist in two forms: vertical with the ring (axial) and peripheral with the ring (equatorial).
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Chapter 4 Solutions
Organic Chemistry: Structure and Function
- Determine if the following salt is neutral, acidic or basic. If acidic or basic, write the appropriate equilibrium equation for the acid or base that exists when the salt is dissolved in aqueous solution. If neutral, simply write only NR. Be sure to include the proper phases for all species within the reaction LiNO3arrow_forwardAn unknown weak acid with a concentration of 0.410 M has a pH of 5.600. What is the Ka of the weak acid?arrow_forward(racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehydearrow_forward
- R₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…arrow_forwardProvide the reasonable steps to achieve the following synthesis.arrow_forwardIdentify which compound is more acidic. Justify your choice.arrow_forward
- Provide the reasonable steps to achieve the following synthesis.arrow_forwardWhen anisole is treated with excess bromine, the reaction gives a product which shows two singlets in 1H NMR. Draw the product.arrow_forward(ii) Draw a reasonable mechanism for the following reaction: CI NaOH heat OH (hint: SNAr Reaction) :arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning