
Concept explainers
(a)
Interpretation:
The most stable chair conformation of the given molecule is to be drawn in which a
Concept introduction:
According to VSEPR theory,
The most stable chair confirmation of disubstituted cyclohexane is the one in which the larger substituent occupies the equatorial position.
In disubstituted cyclohexane, the substituents which are on the same side are cis to each other whereas substituents which are on the opposite side of the ring are trans to each other. If there is more than one substituent attached, then the conformation in which maximum substituents are in equatorial position is favored and is the most stable. Substituents that are trans to each other in one chair conformation remain trans after the chair flip, whereas substituents that are cis remain cis to each other during the ring flip.

Answer to Problem 4.70P
The most stable conformation of the given molecule is:
Explanation of Solution
The given molecule is:
In the given molecule, there is a six member cyclic structure containing carbonyl group as a part of the ring. Thus, it is cyclohexanone. It has two substituents attached which are tertiary butyl group and a methyl group at C3 and C5 carbon atoms of cyclohexanone. Both substituents are trans to each other, as they lie on the opposite side of the ring. The tertiary butyl group is the bulkier substituent on the ring, and it is more stable in an equatorial position. Begin by drawing a chair conformation with a tertiary butyl group in an equatorial position. It is shown by a wedge bond, hence, it must point up in the chair conformation. The tertiary butyl group is pointed up and the methyl group must point down, for them to be trans, hence, the methyl group occupies the axial position as shown below:
If the chair is flipped, the equatorial tertiary butyl group becomes axial. The chair conformation having the bulkier tertiary butyl group in axial position is not stable. Hence, the most stable chair conformation of the given molecule is:
The most stable conformation of the given molecule has one substituent at equatorial position and another at axial position.
Interpretation:
The most stable chair conformation of the given molecule is to be drawn in which a
Concept introduction:
According to VSEPR theory,
The most stable chair confirmation of disubstituted cyclohexane is the one in which the larger substituent occupies equatorial position.
In disubstituted cyclohexane, the substituents which are on the same side are cis to each other whereas substituents which are on the opposite side of the ring are trans to each other. If there is more than one substituent attached, then the conformation in which maximum substituents are in equatorial position is favored and is the most stable. Substituents that are trans to each other in one chair conformation remain trans after the chair flip, whereas substituents that are cis remain cis to each other during the ring flip.

Answer to Problem 4.70P
The most stable conformation of the given molecule is:
Explanation of Solution
The given molecule is:
In the given molecule, there is a six member cyclic structure containing carbonyl group as a part of the ring. Thus, it is cyclohexanone. It has two substituents attached which are fluorine and bromine atoms at C3 and C4 carbon atoms of cyclohexanone. Both substituents are cis to each other, as they lie on the same side of the ring. Out of the two substituents, bromine atom is the largest substituent on the ring, and it is more stable in an equatorial position. Begin by drawing a chair conformation with bromine atom in equatorial position. It is shown by a wedge bond, hence, it must point up in the chair conformation. The bromine atom is pointed up and the fluorine atom must also point up for them to be cis, hence the fluorine atom occupies an axial position as shown below:
If the chair is flipped, the equatorial bromine atom becomes axial. The chair conformation having the bulkier group in equatorial position is more stable. Hence, the most stable chair conformation of the given molecule is:
The most stable conformation of the given molecule has one substituent at equatorial position and another at axial position.
(c)
Interpretation:
The most stable conformation of the given molecule is to be drawn.
Concept introduction:
According to VSEPR theory,
The most stable chair confirmation of disubstituted cyclohexane is the one in which the larger substituent occupies the equatorial position.
In disubstituted cyclohexane, the substituents which are on the same side are cis to each other whereas substituents which are on the opposite side of the ring are trans to each other. If there is more than one substituent attached, then the conformation in which maximum substituents are in equatorial position is favored and is the most stable. Substituents that are trans to each other in one chair conformation remains trans after the chair flip, whereas substituents that are cis remain cis to each other during the ring flip.

Answer to Problem 4.70P
The most stable conformation of the given molecule is:
Explanation of Solution
The given molecule is:
In the given molecule, there is a six member cyclic structure containing carbonyl group as a part of the ring. Thus, it is cyclohexanone. It has two substituents attached which are isopropyl group and methyl group at C3 and C5 carbon atoms of cyclohexanone. Both substituents are cis to each other as they lie on the same side of the ring. The isopropyl group is the largest substituent on the ring, and it is more stable in an equatorial position. Begin by drawing a chair conformation with isopropyl group in the equatorial position. It is shown by a wedge bond, hence, it must point up in the chair conformation. The isopropyl group is pointed up and the methyl group must also point up for them to be cis hence the methyl group goes to another equatorial position as shown below:
If the chair is flipped, both equatorial groups become axial. The chair conformation having the bulkier group in equatorial position is more stable. Hence, the most stable chair conformation of the given molecule is:
The most stable conformation of the given molecule has both substituents in equatorial position.
(d)
Interpretation:
The most stable conformation of the given molecule is to be drawn.
Concept introduction:
According to VSEPR theory,
The most stable chair confirmation of disubstituted cyclohexane is the one in which the larger substituent occupies the equatorial position.
In disubstituted cyclohexane, the substituents which are on the same side are cis to each other whereas substituents which are on the opposite side of the ring are trans to each other. If there is more than one substituent attached, then the conformation in which maximum substituents are in equatorial position is favored and is the most stable. Substituents that are trans to each other in one chair conformation remain trans after the chair flip, whereas substituents that are cis remain cis to each other during the ring flip.

Answer to Problem 4.70P
The most stable conformation of the given molecule is:
Explanation of Solution
The given molecule is:
In the given molecule, there is a six member cyclic structure containing carbonyl group as a part of the ring. Thus, it is cyclohexanone. It has two substituents attached which are fluorine and bromine atoms at C3 and C4 carbon atoms of cyclohexanone. Both substituents are trans to each other, as they lie on the opposite side of the ring. Out of the two substituents, the isopropyl group is the largest substituent on the ring, and it is more stable in an equatorial position. Begin by drawing a chair conformation with isopropyl group in equatorial position. It is shown by a wedge bond, hence, it must point up in the chair conformation. The isopropyl group is pointed up and the methyl group must point down for them to be trans, hence the methyl group goes to axial position as shown below:
If the chair is flipped, the equatorial Isopropyl group becomes axial. The chair conformation having the bulkier group in equatorial position is more stable. Hence, the most stable chair conformation of the given molecule is:
The most stable conformation of the given molecule has one substituent at equatorial position and another at axial position.
(e)
Interpretation:
The most stable conformation of the given molecule is to be drawn.
Concept introduction:
According to VSEPR theory,
The most stable chair confirmation of disubstituted cyclohexane is the one in which the larger substituent occupies the equatorial position.
In disubstituted cyclohexane, the substituents which are on the same side are cis to each other whereas substituents which are on the opposite side of the ring are trans to each other. If there is more than one substituent attached, then the conformation in which maximum substituents are in equatorial position is favored and is the most stable. Substituents that are trans to each other in one chair conformation remain trans after the chair flip, whereas substituents that are cis remain cis to each other during the ring flip.

Answer to Problem 4.70P
The most stable conformation of the given molecule is:
Explanation of Solution
The given molecule is:
In the given molecule, there is a six membered cyclic structure containing ester group as a part of the ring. It has one substituent attached which is a ethyl group not shown by a wedge or dash bond. Thus, the ethyl group can be placed above or below the plane of the ring. The ethyl group is more stable at equatorial position than axial position. Thus, the most stable chair conformation of the given molecule is:
The most stable chair conformation of the given molecule has the bulkier substituent at equatorial position.
Want to see more full solutions like this?
Chapter 4 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Drawing Arrows THE Problem 33 of 35 N. C:0 Na + Submit Drag To Pan +arrow_forwardDraw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore and inorganic byproducts.arrow_forwardDraw the major producrs of this SN1 reaction. Ignore any inorganic byproducts. Use a dash or wedge bond to indicate the sereochemistry of substituents on asymmetric centers where appllicable.arrow_forward
- 5) Oxaloacetic Acid is an important intermediate in the biosynthesis of citric acid. Synthesize oxaloacetic acid using a mixed Claisen Condensation reaction with two different esters and a sodium ethoxide base. Give your answer as a scheme Hint 1: Your final acid product is producing using a decarboxylation reaction. Hint 2: Look up the structure of oxalic acid. HO all OH oxaloacetic acidarrow_forward20. The Brusselator. This hypothetical system was first proposed by a group work- ing in Brussels [see Prigogine and Lefever (1968)] in connection with spatially nonuniform chemical patterns. Because certain steps involve trimolecular reac tions, it is not a model of any real chemical system but rather a prototype that has been studied extensively. The reaction steps are A-X. B+X-Y+D. 2X+ Y-3X, X-E. 305 It is assumed that concentrations of A, B, D, and E are kept artificially con stant so that only X and Y vary with time. (a) Show that if all rate constants are chosen appropriately, the equations de scribing a Brusselator are: dt A-(B+ 1)x + x²y, dy =Bx-x²y. diarrow_forwardProblem 3. Provide a mechanism for the following transformation: H₂SO A Me. Me Me Me Mearrow_forward
- You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: xi 1. ☑ 2. H₂O хе i Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. There is no reagent that will make this synthesis work without complications. : ☐ S ☐arrow_forwardPredict the major products of this organic reaction: H OH 1. LiAlH4 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. G C टेarrow_forwardFor each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 CI MgCl ? Will the first product that forms in this reaction create a new CC bond? Yes No MgBr ? Will the first product that forms in this reaction create a new CC bond? Yes No G टेarrow_forward
- For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. དྲ。 ✗MgBr ? O CI Will the first product that forms in this reaction create a new C-C bond? Yes No • ? Will the first product that forms in this reaction create a new CC bond? Yes No × : ☐ Xarrow_forwardPredict the major products of this organic reaction: OH NaBH4 H ? CH3OH Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. ☐ : Sarrow_forwardPredict the major products of this organic reaction: 1. LIAIHA 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. X : ☐arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

