Concept explainers
Interpretation:
The curve showing energy change from the rotation of
Concept introduction:
Newman projected two types of spatial arrangements of molecules which are staggered and eclipsed Newman projections.
Staggered conformation is the arrangement of atoms or groups of atoms in a molecule resulting in a
Eclipsed conformation is the arrangement of atoms or groups of atoms in a molecule resulting in a
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Organic Chemistry
- 3B. For each compound below, draw two chair conformations. Indicate whether the substituents are axial or equatorial. Indicate which chair conformation is more stable. (you need to draw conformations of the exact molecule, not its mirror image or diastereomer) (a) (b) (c) Ме Me Et "Et Et Mearrow_forwardIf either of the following molecules has a stereogenic carbon (chirality center), give structures for both of the enantiomers. (a) 2-bromopropane (b) 2-bromobutanearrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forward(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw Newman projections for the conformations in which -CH3 and -Br are gauche (dihedral angles 60° and 300°).arrow_forward
- (b) Consider the following tetra-substituted cyclohexane: OH Draw the alternative chair conformations of the cyclohexane compound, shown above. List the unfavourable steric interactions for each chair conformation and determine the more stable conformation of the compound. i.arrow_forward3. (20) Cyclohexane may go through ring-flipping as shown below. 5 (a) Draw both of the possible chair conformations for cis-1-tert-butyl-4-methylcyclohexane by copying the scheme above followed by adding appropriate substituents to axial or equatorial positions. (b) Circle the more stable conforms of (A) and (B)arrow_forwarda) Considering compounds 2a through 21, identify: ONE PAIR of geometric isomers; TWO PAIRS of enantiomers and THREE PAIRS of identical molecules. b) Give the names, including the configurations, of each of the geometric isomers and of each of the enantiomers. Draw the relevant structures in the space provided in the Answer Booklet. c) Sort compounds 2a, 2b, 2c, 2f and 2k in order of increasing solubility in water and briefly justify your ordering. 2 НО. AH H H anulta HOwno barwolset of ef 28nuor OH 2bc 2c ning) bi 10291 H WH 2 st brbot di OH Lacenoqoid OH to nabio ni one nt at dit st 2e OH "H OH bre 2a 2d 2g 2j H HO 2h 2k HO ...H di al nt o 2f 2i 21arrow_forward
- Following are the alternative chair conformations for trans-1,2-dimethylcyclohexane.(a) Estimate the difference in free energy between these two conformations.(b) Given your value in (a), calculate the percent of each chair present in anequilibrium mixture of the two at 25°C.arrow_forwardPRACTICE PROBLEM 2.25 The compounds in each part below have the same (or similar) molecular weights. Which compound in each part would you expect to have the higher boiling point? Éxplain your answers. OH or HO. (a) (c) но OH or (b) (CHa),N orarrow_forwardG.170.arrow_forward
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