Worksheet Alkenes Sbi 09

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 a. 3,3,4,4,tetrabromohexane CH3CH2CBr2CBr2CH2CH3

Response Boxes

Reagents

Starting Material

1. H2O + H2SO4 + HgSO4

Reagent Number

2. H2 + Lindlar catalyst (poisoned palladium) 3. NaBH4 in ethyl

alcohol

b. 3-hexanone CH3(CH2)2COCH2CH3

Starting Material

4. Disiamylborane [(C5H11)2BH] followed by H2O2 in base

Reagent Number

5. Br2 (2 equivalents) 6. KMnO4 in H2O or ozone

Starting Material c. propanoic acid CH3CH2CO2H

Reagent Number

7. HBr (2 equivalents) 8. Na in liquid ammonia (NH3) 9. NaOH in aqueous ethanol

Starting Material d. hexanal CH3(CH2)4CHO

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

Reagent Number

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 transCH3CH2CH=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 (ii) Ethyl bromide

(1 equivalent)

Predict the product from the reactions!!! Bottom of Form

Bottom of Form