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Organic Chemistry I

Semester August-December 2017


Chapter 2. ALKANES AND CYCLOALKANES

Exercises-Part 1
Part 1. Nomenclature.

1. An n-alkane of molecular formula C28H58 has been isolated from a certain fossil
plant. Write a condensed structural formula for this alkane.
2. Much of the communication between insects involves chemical messengers called
pheromones. One of the principal components of this aggregation pheromone is the
alkane shown in the bond-line formula that follows. Give the molecular formula of
this substance, and represent it by a condensed formula.

3. Write condensed and bond-line formulas for the five isomeric C6H14 alkanes.

4. Phytane is a naturally ocurring alkane produced by the alga Spirogyra and is a


constituent of petrolueum. The IUPAC name of phytane is 2,6,10,14-
tetramethylhexadecane. Write a structural formula for phytane.

5. Derive the IUPAC names for:


a) The isomers of C4H10 c) (CH3)3CCH2CH(CH3)2
b) The isomers of C5H12 d) (CH3)3CC(CH3)3
o o
Clasified the C´s and H´s as 1 , 2 , and so on.

6. Write an acceptable IUPAC name for each of the following alkanes:

7. Name each of the following compounds:


a) b) c)

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8. Match the boiling points with the apropiate alkanes. Explain your answer.
Alkanes: octane, 2-methyl-heptane, 2,2,3,3- tetramethylbutane, nonane
bp (°C, 1atm): 106, 116, 126, 151.

Compound octane 2-methyl- 2,2,3,3- nonane


heptane tetramethylbutane
Boiling Point
(°C, 1 atm)
Structure

9. i) Complete the structure of the pain-relieving drug ibuprofen on the basis of the the
fact that it is a carboxylic acid that has the molecular formula C13H18O, X is an
isobutyl group, and Y is a methyl group.

ii) Mandelonitrile may be obtained from peach flowers. Derive its structure from the
template in part (i) given that X is hydrogen, Y is the functional group that
characterized alcohols, and Z characterizes nitriles.

10. Uscharidin is the commun name of a poisonous natural product having the structure
shown.Locate all of the following in this molecule:
(a) Alcohol, aldehyde, ketone and ester functional groups
(b) Methylene groups
(c) Primary carbons
O

O
CH3

O O
OH H CH H
O

OH

H 3C O O
H H H

San Miguel de Urcuquí | Hacienda San José s/n y Proyecto Yachay | T: + 593 6 299 9130 ext: 2614
info@yachaytech.edu.ec | www.yachaytech.edu.ec