Concept explainers
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(a)
Interpretation:
The Newman projections of the most stable conformations about each of the carbon-carbon bonds in the principal chain of the compound
Concept introduction:
Newman projection is a way of representing the groups attached to carbon atoms in the
The line-and-wedge representation is used to show the molecule in three dimensions.
The sawhorse representation is used to show the above carbon atom on right side in a molecule.
(b)
Interpretation:
The most stable conformation of
Concept introduction:
Newman projection is a way of representing the groups attached to carbon atoms in the
The line-and-wedge representation is used to show the molecule in three dimensions.
The sawhorse representation is used to show the above carbon atom on right side in a molecule.
(c)
Interpretation:
The line-and-wedge structure of the conformation derived in (b) is to be drawn.
Concept introduction:
Newman projection is a way of representing the groups attached to carbon atoms in the
The line-and-wedge representation is used to show the molecule in three dimensions.
The sawhorse representation is used to show the above carbon atom on right side in a molecule.
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Chapter 2 Solutions
Organic Chemistry
- For 1,2-dichloroethane: (a) Draw Newman projections for all eclipsed conformations formed by rotation from 0 to 360° about the carbon-carbon single bond. (b) Which eclipsed conformation(s) has the lowest energy? Which has the highest energy? (c) Which, if any, of these eclipsed conformations 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_forwardDraw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3- dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a ) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?arrow_forward
- The skeletal line formula for a branched alkene is shown below. (i) What is the molecular formula of this compound? (ii) How many carbon atoms are in the longest chain, ignoring the double bond? (iii) What is the longest chain incorporating both carbons of the double bond? (iv) How many substituents are on this chain? (v) Give the IUPAC name for this compound. [6]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_forwardHO₂ H COOH COOH V POH HOT COOH cooff VI Ho HO COOH COOH VI H H COOH COOH VIIL OH OH Question: In the structures / examples abovke Identify V, VI, VII and VIII as Identical enantiomers, ciastereomes, stereo/cumers and/or structural isomers (there are 6 pairs 7 Comp eand to discover te I&T I TEN TEM TIMIN).arrow_forward
- Sight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forwardDraw 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 interactionarrow_forwarddraw the most stable conformation of (a) ethylcyclohexane (b) 3-isopropyl-1,1-dimethylcyclohexanearrow_forward
- (a) Draw the most stable chair conformers of trans-1,3-diisopropylcyclohexane and trans-1,4-diisopropylcyclohexane. (b) Which is more stable: trans-1,3-diisopropylcyclohexane or trans-1,4-diisopropylcyclohexane?arrow_forward3)) Draw the most stable chair conformation of a 1,2,4-trimethylcyclohexane (Show all the hydrogens and indicate if the bond is axial or equatorial at the substitution).arrow_forwardDraw the most stable conformation of cis-1-tert-butyl-3-ethylcyclohexane. (a) (b) trans-1-tert-butyl-2-methylcyclohexane. (c) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.arrow_forward
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