Texas Woman University Chemistry Worksheet

1. Which of the indicated carbon-carbon bonds is shorter?
2. How many elements of unsaturation do molecules with a molecular formula of C8H4N2
3. Give the structures of three examples of molecules that have a molecular formula of
C6H8. One of the structures should have only one ring and one of the structures should
have no rings.
4. Provide an acceptable name for (CH3)2CHCH=C(CH3)CH2CH3.
5. Draw an acceptable structure for 4-phenylbut-1-ene.
6. Draw and name the six alkenes which have the molecular formula C5H10.
7. Does the alkene shown below violate Bredt’s rule?
8. Which is the more stable diene shown below? Briefly explain your answer.
9. Dehydrohalogenation of an alkyl halide by treating it with a strong base to yield an
alkene product typically occurs by what reaction mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) free radical
10. Propose a synthesis to convert 2-butanol to butane.
11. Draw a mechanism and use a chair structure to explain the major product that is formed
in the reaction below.
12. Propose a detailed, step-by-step mechanism for the reaction pathway shown below.
13. Propose a detailed, step-by-step mechanism for the reaction pathway shown below.
14. Predict the major product of the following reaction.
Based on the relative stabilities of the intermediates involved, explain the basis for
Markovinkov’s rule in the addition of hydrogen halides to alkenes.
Draw the major organic product generated in the reaction below. Pay particular
attention to regio- and stereochemical detail.
17. Treatment of cyclopentene with peroxybenzoic acid ________.
18. Provide the IUPAC name for the compound below.
19. Complete the following reaction sequences below by filling-in the missing reagents
or structures.
20. Complete the following reaction by filling in the necessary reagents.

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