1

Organic Chemistry I
Test 1 Isomers/Resonance Recognition Practice.

T Note: You should be able to practice the first page fairly early during the class lectures.
Same name, condensed formula.
• The second page you won’t be able to process until almost the end, after completionBut atomsof thebechapter
can't superimposed, even
dealing with Newman Projections and Cyclohexane Chair conformations. by single bond rotation.
Two families:
1. Unequal mirror images (enantiomers)
For the following pairs, classify the relationship between each pair as either: 2. Cis/trans (diastereomers)
• same compound • structural isomers • resonance structures • stereoisomers
Remember, single bonds can rotate, Different condensed formula, No atoms move. Formal charge,
but double bonds can't. Different name double bonds, lone pairs may.

2.
1. 3.

4. H CH 3
5.
6. H

H CH 3

7. 8. 9. H
T Single bond rotation OK

10. 11.
12.

OH OH OH OH OH

13. 14. OH 15.

OH O O
O O O
16.
17. 18.

T
H Br H Br Br H Br H H Br H Br H Br BrH H Br H Br H Br
19. 20.
21. Br H

H Br H Cl H Cl H Br H Br H Cl H Br H Cl Cl H Br H
22. 23. H Cl H Br 24.
 2
For the following pairs, classify the relationship between each pair as either:
• same compound • structural isomers • resonance structures • stereoisomers

CH2CH 3 CH2CH 3 iPr iPr

T H H
H CH 3 H H H H

H H H H H H
CH 3 H H 3C
25. H
26.
CH 3 H

H CH 3 H CH 3

27. H (Note: review video 28. H

discussion of this problem in the context of the
Newman projections.)

iPr H iPr iPr

H H H 3C H H H H H

H CH 3 H 3C iPr H CH 3 H H
CH 3 CH 3 CH2CH 3
T 29. H 30.

H H H H
H
H Br Br H Br Br
H Br
31. Br Br
32. Br

H H H Br

Br Br H Br H Br
H Br
34. Br H
33. Br H
T

Br Br Br H
H H H H
H H Br
H 36. Br Br
35. Br Br