Work Sheet Organic Chemistry I

Chapter 3. Alkenes and Alkynes

1. Draw the Structural Formula for :

a) 3-ethyl-5-methyl-3-heptene
b) 4-bromo-1-ethylcyclopentene
c) 6-cyclopropyl-2-methyl-4-propyl-2-heptene
d) 6-bromo-2-cyclopentyl-6-vinyl-1,3-cyclooctadieneTop of Form

1. Assign a configurational prefix, E or Z to each structure :

2. Predict the favored product in examples such as those shown below:

 4. Top of Form
Alkyne Reactions
Two isomeric alkyne starting materials are A. 3-hexyne CH3CH2C≡CCH2CH3
available for your use. They are:
B. 1-hexyne CH3(CH2)3C≡CH
Using one or the other of these compounds, and selecting reagents from the list on the right, indicate how the following
products might be prepared.
Each question (a. through h.) requires two responses. Under Starting Material enter A or B. Under Reagents enter a
number corresponding to your selection.

Desired Product Response Boxes Reagents

1. H2O + H2SO4 +
a. 3,3,4,4,tetrabromohexane Starting Material HgSO4
CH3CH2CBr2CBr2CH2CH3
2. H2 + Lindlar catalyst
Reagent Number (poisoned
palladium)

3. NaBH4 in ethyl
 alcohol

4. Disiamylborane
Starting Material [(C5H11)2BH]
followed by H2O2 in
base
b. 3-hexanone CH3(CH2)2COCH2CH3 5. Br2 (2 equivalents)
Reagent Number

6. KMnO4 in H2O
or ozone

Starting Material 7. HBr (2 equivalents)

8. Na in liquid
c. propanoic acid CH3CH2CO2H ammonia (NH3)
Reagent Number
9. NaOH in aqueous
ethanol

Starting Material

d. hexanal CH3(CH2)4CHO
Reagent Number

e. cis-3-hexene cis-CH3CH2CH=CHCH2CH3 Starting Material

 Reagent Number

Starting Material

f. 2-hexanone CH3CO(CH2)3CH3
Reagent Number

Starting Material

g. 2,2-dibromohexane CH3CBr2(CH2)3CH3
Reagent Number

Starting Material

h. trans-3-hexene trans-
CH3CH2CH=CHCH2CH3 Reagent Number
5. TTop of Form

hree alkyne reactants:

A. ethyne (acetylene)
B. 1-butyne
C. 2-butyne

These compounds may be reacted with nine different reagents:

1. Hydrogen & Lindlar catalyst
2. Hydrogen Chloride (1 equivalent)
3. (i) Disiamylborane, R2BH
(ii) H2O2 in NaOH soln.
4. Hydrogen & Pt catalyst
5. Sodium in liq. Ammonia
6. H3O(+) & HgSO4
7. Bromine (2 equivalents)
8. Hydrogen Chloride (2 equivalents)
9. (i) Sodium Amide (1 equivalent)
(ii) Ethyl bromide
Predict the product from the reactions!!!

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