I.
REACTION OF ALKENES: Predict the structure of the product.
1
2
II.
REACTION OF ALKYNES: Predict the structure of the product.
3
4
III.
ORGANIC SYNTHESIS
A. Illustrate the reaction and identify the reagent used in the following synthesis:
1. 1,2-dimethylcyclohexane from 1,2-dimethylcyclohexa-1,3-diene
2. trans-1,2-diphenylacetylene (byproduct: sodium iodide and ammonia) from ethynylbenzene
3. 3-ethyloctan-2-ol from 3-ethyloct-2-ene.
4. 3-methylpentane-1,5-dioic acid from 3-methylcyclopentene
5. (Z)-hex-3-ene from hex-3-yne
6. But-2-yne from 2,3-dibromobutane
5
7. Hexa-2,3-diol from hex-2-ene
8. 3-methylbutanoic acid (byproduct: carbon dioxide) from 4-methylpentyne
9. A racemic mixture of trans-1-ethyl-2-iodocyclopentanol from 1-ethylcyclopentene
10. 2,2,3,3,5,5,6,6-octachloroheptane from hepta-2,5-diyne
B. Predict the structure and the IUPAC name of the substrate/s if it was an:
1. Alkyne
6
Butyne
2. Alkane (four possible alkanes)
(1-halopropyl)cyclopentane or 1halo-1-cyclopentylpropane
(2-halopropyl)cyclopentane or 2halo-1-cyclopentylpropane
(1-hydroxypropyl)cyclopentane or
1-cyclopentylpropanol
(2-hydroxypropyl)cyclopentane or
1-cyclopentylpropan-2-ol
or
1-
cyclopentylisopropanol
3. Alkyne
1-(prop-1-ynyl)cyclopentane or
1-cyclopentylpropyne
4. Alkene
Cyclooctene
5. Alkyne
7
Cyclooctyne
6. Alkene
Hept-2-yne
7. Alkene
Pent-2-yne
8. Alkene
Diphenylethylene
9. Alkene
1,2-dichloro-3,4,5trimethylheptene
10. Alkyne
8
3,4,5-trimethylheptyne
11. Alkane
1-isopropyl-2-methylcyclopentane
12. Alkenylated Alkane
1-methyl-2-(propan-2ylidene)cyclopentane
13. Alkene
5-isopropyl-2-methylhept-3-ene or
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5-ethyl-2,6-dimethylhept-3-ene
14. Alkyne
5-isopropyl-2-methylhept-3-yne or
5-ethyl-2,6-dimethylhept-3-yne
15. Alkene
6-ethyl-5-propylundec-5-ene
16. Alkyne
Oct-3-yne
C. Complete the following synthesis by indicating the missing reagent and/or drawing the
structure of the missing substrate and/or product.
i.
ii.
10
iii.
iv.
11
v.
12