10.1,2-dichlorocyclohexane Draw the two geometric isomers that are possible for this molecule and build the corresponding models. As you did on page 7, use dashes/wedges for the chlorine groups, but lines for the rest of In this case, the chair conformations are not all equal. By performing a ring flip, you will see that sometimes the chlorine substituents are axial, while sometimes they are equatorial. For each geometric isomer above, there are two possible conformations. Draw them below, then rank them in terms of stability. Keep in mind that the most stable conformations will have the largest substituents in the equatorial positions. 10

10.1,2-dichlorocyclohexane Draw the two geometric isomers that are possible for this molecule and build the corresponding models. As you did on page 7, use dashes/wedges for the chlorine groups, but lines for the rest of In this case, the chair conformations are not all equal. By performing a ring flip, you will see that sometimes the chlorine substituents are axial, while sometimes they are equatorial. For each geometric isomer above, there are two possible conformations. Draw them below, then rank them in terms of stability. Keep in mind that the most stable conformations will have the largest substituents in the equatorial positions. 10

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.61P: Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used...

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(a) What is the IUPAC name for the following molecule (including absolute configurations if required)? (b) Draw the Newman projections looking down the C3-C4 bond that represent all the three staggered conformations for the molecule shown above. (c) Given that the strain energies below, calculate the strain energies for each conformer and identify which is the most stable. Gauche interaction Strain Energy HOCH3 0.0 kJ mol- HOCH;CH; |0.4 kJ mol- 3.8 kJ mol- | 4.3 kJ mol- CH;CH3 CH;CH2CH3 |CH2CH; CH2CH; 4.6 kJ mol- Newman Projection of Conformer 1 Strain Energy of Conformer 1 Newman Projection of Conformer 2 Strain Energy of Conformer 2 Newman Projection of Conformer 3 Strain Energy of Conformer 3
It is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D configuration and what conformation (axial,equatorial) would each of the three ethyl groups be in for the most stable configuration.
b. Please complete the zig-zag conformation of the compound (3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes. 4
Chemistry 9) Write Newman projections for the gauche and anti-conformations of 1,2- dibromoethane (BrCH2CH2Br). Which conformation is more stable than the other and explain why?
Square planar molecules with formula AB2C2 and octahedral molecules with formulas AB4C2 and AB3C3 feature diastereoisomers. Recall that trigonal bipyramidal geometry features two distinct positions: axial and equatorial. Draw all diastereoisomers for trigonal bipyramidal molecules with formula (a) AB4C and (b) AB3C2. You must indicate the stereochemistry using full and dashed wedges and label all positions as either axial (ax) and equatorial (eq)..
1. Write condensed structural formula for all isomers of compounds that fulfill the following requirements: (a) Alkenes with molecular formula CsH10. (b) Alkynes with molecular formula C4H6. (c) Dienes with molecular formula C4H6. 2. For each of the following, give the order of increasing boiling point: (a) n-Heptane, n-octane and n-hexane. (b) n-Pentane, isopentane and n-hexane. (c) 2-Methylhexane, n-heptane and 3,3-dimethylpentane. 9 3. Isomeric compounds can sometimes be distinguished by observing the number of mono- brominated compounds that each forms. In the following cases decide which isomer is present by the number of compounds that are formed. (a) Compound A forms four monobromo compounds. Is it 2-methylbutane or n-pentane? (b) CompoundB forms four monobromo compounds. Is it 2- methylpentane or 3- methylpentane? (c) Compounds C forms monobromo compound. Is it cyclopentane or one mehtylcyclopentane? 4. A hydrocarbon C5H12 was allowed to react with bromine. Only monobromo…
Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.
Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.
Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.
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Draw Newman projections for the anti, eclipsed, gauche and fully eclipsed conformations of Butane. Indicate their relative stabilities and the reasons for your ranking-need to discuss the stresses involved in each case. Using suitable specific conformers of specific structures as examples, explain the difference between (a) angle strain (b) torsional strain and (c) steric strain. Need to draw the confomers and structures 4) Draw the most stable conformers using chair structures of the following: (c) cis-1,2-Dibromocyclohexane (d) trans-1,2-Dibromocyclohexane (e) cis-Decalin (f) trans-Decalin . Draw the most stable conformers of trans-1-Bromo-4-methylcyclohexane and cis-1-Bromo-4-methylcyclohexane. Which is more stable? Explain the reason for your answer. Need to include a discussion of 1,3-Diaxial interaction
5. For the molecules below assign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither. b) RSN RSN HO" RSN EZ N RSN НО. H₂N HO HO OH HO OH RSN RSN CH3 НИ H3 CH₂ RSN RSN RSN EZ N RSN