
Concept explainers
(a)
Interpretation:
Chair conformations of structure (1) and (2) have to be drawn for six-membered rings; the lowest energy conformations for the compound have to be drawn.
Concept Introduction:
Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.
Drawing Axial and Equatorial substituents:
Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. the other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.
Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.
Newman projections: The new conformations of compounds can be drawn and analyzed by Newman projections. A Newman projection visualizes different conformations of Carbon-carbon
The angle between two hydrogens of a Newman projection is called as dihedral angle or torsional angle. This dihedral angle changes as the C-C bond rotates. Two conformations with special attentions are staggered and eclipsed conformation. Staggered conformation is the lowest in energy and the eclipsed conformation is the highest in energy.
For example,
Anti-conformation: The conformation with a dihedral angle of
The two methyl groups achieve maximum separation from each other. In other, methyl groups are closer to each other; their electron clouds are repelling each other, causing an increase in energy. This unfavorable interaction is called gauche interaction.
Conversion of chair conformation into Newman projection:
Ring flipping between Newman projections:
Ring flipping is a conformational change that is accomplished only through a rotation of all C-C single bonds. On ring flipping between two chair conformation equatorial changes into axial and vice-versa.
(b)
Interpretation:
The larger heat of combustion out of the given compounds has to be identified and explained.
Concept Introduction:
Nomenclature of organic compounds:
Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.
Drawing Axial and Equatorial substituents:
Each carbon in cyclohexane can bear two substituents. One group is said to occupy an axial position, which is parallel to a vertical axis passing through the center of the ring. the other group is said to occupy an equatorial position, which is positioned approximately along the equator of the ring.
Conformations: Rotation about C-C single bonds allows a compound to adopt a variety of possible three-dimensional shapes.
Newman projections: The new conformations of compounds can be drawn and analyzed by Newman projections. A Newman projection visualizes different conformations of Carbon-carbon chemical bond from front to back with the front carbon represented as a black dot and the back represented as a circle.
The angle between two hydrogens of a Newman projection is called as dihedral angle or torsional angle. This dihedral angle changes as the C-C bond rotates. Two conformations with special attentions are staggered and eclipsed conformation. Staggered conformation is the lowest in energy and the eclipsed conformation is the highest in energy.
For example,
Anti-conformation: The conformation with a dihedral angle of
The two methyl groups achieve maximum separation from each other. In other, methyl groups are closer to each other; their electron clouds are repelling each other, causing an increase in energy. This unfavorable interaction is called gauche interaction.
Conversion of chair conformation into Newman projection:
Ring flipping between Newman projections:
Ring flipping is a conformational change that is accomplished only through a rotation of all C-C single bonds. On ring flipping between two chair conformation equatorial changes into axial and vice-versa.

Want to see the full answer?
Check out a sample textbook solution
Chapter 4 Solutions
Organic Chemistry 3rd.ed. Klein Evaluation/desk Copy
- Calculating the pH at equivalence of a titration Try Again Your answer is incorrect. 0/5 a A chemist titrates 70.0 mL of a 0.7089 M hydrocyanic acid (HCN) solution with 0.4574M KOH solution at 25 °C. Calculate the pH at equivalence. The pK of hydrocyanic acid is 9.21. Round your answer to 2 decimal places. Note for advanced students: you may assume the total volume of the solution equals the initial volume plus the volume of KOH solution added. pH = 11.43] G 00. 18 Ar B•arrow_forwardBiological Macromolecules Naming and drawing the products of aldose oxidation and reduction aw a Fischer projection of the molecule that would produce L-ribonic acid if it were subjected to mildly oxidizing reaction conditions. Click and drag to start drawing a structure. X AP ‡ 1/5 Naor Explanation Check McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center Accessibilarrow_forward● Biological Macromolecules Identifying the parts of a disaccharide Take a look at this molecule, and then answer the questions in the table below it. CH2OH O H H H OH OH OH H H CH2OH H O OH H OH H H H H OH Is this a reducing sugar? Does this molecule contain a glycosidic bond? If you said this molecule does contain a glycosidic bond, write the symbol describing it. If you said this molecule does contain a glycosidic bond, write the common names (including anomer and enantiomer labels) of the molecules that would be released if that bond were hydrolyzed. If there's more than one molecule, separate each name with a comma. Explanation Check O yes X O no ○ yes O no Uarrow_forward
- The aim of the lab is to measure the sodium content from tomato sauce using the Mohr titration method. There are two groups being: Regular Tomato sauce & Salt Reduced tomato sauce QUESTION: State how you would prepare both Regular & Salt reduced tomato sauce samples for chemical analysis using the Mohr titration methodarrow_forwardUsing the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds faster at temperatures above -48. °C. ΔΗ is (pick one) ✓ AS is (pick one) B This reaction is spontaneous except below 114. °C but proceeds at a slower rate below 135. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is C This reaction is exothermic and proceeds faster at temperatures above -43. °C. (pick one) AS is (pick one) v Х 5 ? 18 Ararrow_forwardion. A student proposes the following Lewis structure for the perchlorate (CIO) io : :0: : Cl : - - : :0: ك Assign a formal charge to each atom in the student's Lewis structure. atom central O formal charge ☐ top O ☐ right O ☐ bottom O ☐ Cl ☐arrow_forward
- Decide whether these proposed Lewis structures are reasonable. proposed Lewis structure Yes. Is the proposed Lewis structure reasonable? Cl- : 2: :Z: :Z: N—N : 0: C C1: O CO No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | Yes. No, it has the wrong number of valence electrons. The correct number is: No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0". ☑arrow_forwardUse the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions ΔΗ is (pick one) A This reaction is faster above 103. °C than below. AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous only above -9. °C. AS is (pick one) ΔΗ is (pick one) C The reverse of this reaction is always spontaneous. AS is (pick one) 18 Ararrow_forwardUse the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds slower at temperatures below 41. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous except above 94. °C. AS is (pick one) This reaction is always spontaneous, but ΔΗ is (pick one) C proceeds slower at temperatures below −14. °C. AS is (pick one) Х 00. 18 Ar 무ㅎ B 1 1arrow_forward
- Draw the product of the reaction shown below. Ignore inorganic byproducts. + H CH3CH2OH HCI Drawingarrow_forwardplease explain this in simple termsarrow_forwardK Most Reactive Na (3 pts) Can the metal activity series (shown on the right) or a standard reduction potential table explain why potassium metal can be prepared from the reaction of molten KCI and Na metal but sodium metal is not prepared from the reaction of molten NaCl and K metal? Show how (not). Ca Mg Al с Zn Fe Sn Pb H Cu Ag Au Least Reactivearrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





