Least Stable Chair Most Stable Chair

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Q1. (a) Methylcyclohexane can exist in two different chair conformations, one of which is 1.8 kcal/molmore stable than the other, i.e., the A value for the methyl group is 1.8. In each of the two boxes below,draw in a bond to one methyl (CH3) group in the appropriate position. (2 pt)CH31!G 1–1.8 kcal/molLeast stable chair1Most stable chair(b) Chlorocyclohexane also exists in two different chair conformations, one of which is 0.6 kcal/molmore stable than the other, i.e., the A value for the chloro group is 0.6. In each of the two boxes below,draw in a bond to one chloro (Cl) group in the appropriate position. (2 pt)Cl1!G 11–0.6 kcal/molLeast stable chairMost stable chair(c) For trans-1-chloro-4-methylcyclohexane (shown below), draw in bonds to CH3 and Cl groups asappropriate, to indicate the least and most stable chair conformers. Assuming that A values are additive(and hence subtractive if necessary.), predict what the ΔG value will be. (6 pt)!G Cl111CH3Least stable chairkcal/molQuestion 1 is continued on the next page.Most stable chair

(d) For cis-1-chloro-4-methylcyclohexane (shown below), draw in bonds to CH3 and Cl groups asappropriate, to indicate the least and most stable chair conformers. Assuming that A values are additive(and hence subtractive if necessary.), predict what the ΔG value will be. (6 pt)!G Cl111CH3Least stable chairkcal/molMost stable chair(e) For the isomer of 1-chloro-3,5-dimethylcyclohexane shown below, draw in bonds to CH3 and Clgroups as appropriate, to indicate the least and most stable chair conformers. Assuming that A valuesare additive (and hence subtractive if necessary.), predict what the ΔG value will be. (8 pt)!G CH3Cl111CH3Least stable chairMost stable chairkcal/mol(f) In the appropriate boxes below, draw the three most stable conformations of cyclohexylcyclohexane (shown to the right) in which the indicatedH atoms maintain an ANTI relationship, i.e., are 180 apart. Once you havedrawn these three different conformers, use the box below them to brieflyexplain your answers. (12 t Stable ConformerExplanation:2nd Most Stable Conformer3rd Most Stable Conformer

Q2. (a) Methylcyclohexane (shown in the middle below) can exist in two different chair conformations,one of which is 1.8 kcal/mol more stable than the other. In each of the top two boxes below, draw in abond to one methyl (Me) group in the appropriate position. In the bottom two boxes, complete theNewman projections by filling in methyl (Me) groups AND hydrogen atoms (H) where appropriate.(4 points)1!G –1.8 kcal/mol1CH3Least stable chair16Most stable chair23542133!G –1.8 kcal/mol12Least stable chairMost stable chair(b) trans-1,4-Dimethylcyclohexane (shown below) also exists in two different chair conformations, one ofwhich is 3.6 kcal/mol more stable than the other. In each of the boxes below, draw in methyl (Me)groups in the appropriate positions. (4 points)CH3CH3!G –3.6 kcal/molLeast stable chairQuestion 3 is continued on the next page.Most stable chair

(c) trans-1,2-Dimethylcyclohexane (shown below) also exists in two different chair conformations, one ofwhich is 2.7 kcal/mol more stable than the other. In each of the boxes below, draw in methyl (Me)groups in the appropriate positions. (4 points)H3C!G –2.7 kcal/molCH3Least stable chairMost stable chair(d) In the box below, explain (using appropriate diagrams if you wish), why the difference in energybetween the two chair conformations of trans-1,2-dimethylcyclohexane is 0.9 kcal/mol LESS than thedifference in energy between the two chair conformations of trans-1,4-dimethylcyclohexane. (8 points)Question 2 is continued on the next page.

For each of the questions below (e–h) draw the most stable chair conformation for each compound, andin each case give a succinct reason for your choice. (Hint: the answers aren’t perhaps as easy as you may thinkthey are.) (2 2 points each)(e)(f)OCH3H3CCH3CH3reason:(g)Brreason:(h)NH3 Ireason:CO2–reason:(i) When the compound in part (h) is treated with a strong acid, a new compound is formed. Draw themost stable chair conformation of this new product and justify your choice (4 points)

Least stable chair Most stable chair 1 1 1 Ð0.6 kcal/mol!G (c) For trans-1-chloro-4-methylcyclohexane (shown below), draw in bonds to CH3 and Cl groups as appropriate, to indicate the least and most stable chair conformers. Assuming that A values are additive (and hence subtractive if necessary.), predict what the ΔG value will be. (6 pt) Cl

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