1 Organic Chemistry I Test 1 Isomers/Resonance Recognition Practice. Note: You should be able to practice the first page fairly early during the class lectures. • The second page you won’t be able to process until almost the end, after completion of the chapter dealing with Newman Projections and Cyclohexane Chair conformations. For the following pairs, classify the relationship between each pair as either: • same compound • structural isomers • resonance structures • stereoisomers 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. H CH 3 H H CH 3 H OH OH OH OH OH OH OH O O O O O Br Br H H H H Br Br Br Br H H Br H H Br Br Br H H Br H H Br Br Cl H H Cl Br H H Br Cl H H Cl Br H H Br Cl H H H H Cl Br T T T Different condensed formula, Different name No atoms move. Formal charge, double bonds, lone pairs may. Same name, condensed formula. But atoms can't be superimposed, even by single bond rotation. Two families: 1. Unequal mirror images (enantiomers) 2. Cis/trans (diastereomers) Remember, single bonds can rotate, but double bonds can't. Single bond rotation OK
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1Organic Chemistry I Test 1 Isomers/Resonance Recognition Practice. Note: You should be able to practice the first page fairly early during the class lectures.
• The second page you won’t be able to process until almost the end, after completion of the chapter dealing with Newman Projections and Cyclohexane Chair conformations.
For the following pairs, classify the relationship between each pair as either: • same compound • structural isomers • resonance structures • stereoisomers
1.
2. 3.
4. 5.
6.
7. 8. 9.
10. 11. 12.
13. 14. 15.
16. 17. 18.
19. 20. 21.
22. 23.
24.
H
CH3H
H
CH3H
OH OH OH
OH
OH OH
OH OO O
O O
Br BrH H H HBr Br Br BrH H Br HH Br Br BrH H BrH
HBr
Br ClH H Cl BrH H Br ClH HCl BrH H
Br ClH H H HCl Br
T
T
T
Different condensed formula,Different name
No atoms move. Formal charge, double bonds, lone pairs may.
Same name, condensed formula. But atoms can't be superimposed, even by single bond rotation. Two families:1. Unequal mirror images (enantiomers)2. Cis/trans (diastereomers)
Remember, single bonds can rotate, but double bonds can't.
Single bond rotation OK
2For the following pairs, classify the relationship between each pair as either: • same compound • structural isomers • resonance structures • stereoisomers
25.
26.
27. (Note: review video discussion of this problem in the context of the Newman projections.)
28.
29.
30.
31.
32.
33.
34.
35.
36.
CH2CH3
HHH
H CH3
CH2CH3
HH CH3
H HiPr
HH3CH
H HiPr
HH CH3
H H
H
CH3H
H
CH3H
H
iPrH3CH
H3C HiPr
CH3H CH3
H HiPr
CH3H CH3
H HiPr
HH CH2CH3
H H
Br
HBrH
Br
HBr H Br
HHBr
Br
HBr
H
Br
HBrH
H
HBr Br
Br
HBrH
H
BrH Br
BrH Br
HBrH
BrH Br
H BrHBr
HH
Br
T
T
T
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