Alkenes, Alkynes & EA Reaction

Roldan M. de Guia Department
of Biochemistry Faculty of Pharmacy University of Santo Tomas

CnAlkenes H2n

Alkynes

Alkenes

Cycloalkenes

Alkynes

Alkenes

Physical Properties
• Alkenes & alkynes are nonpolar • Physical properties are similar to those of alkanes with same C skeletons • Those that are liquid at RT have densities <1.0g/mL

Physical Property: Boiling point

Alkenes have diffuse e- cloud; alkanes have stronger interaction; & alkyne’s π e- cloud is tighter than alkenes

ISOMERISM

STRUCTURE OF ALKENES

Alkenes: cis & trans isomerism
cis trans

H R

H R

R H

H R

All substituents are All substituents are on different sides on one side of π bond of π bond

Alkenes: cis & trans isomerism

Alkenes: cis & trans isomerism

Alkenes: cis & trans isomerism

Cis/trans Isomerism in Cycloalkenes
• For cycloalkenes with 7 or fewer C atoms, the cis configuration is preferred

Cis/trans Isomerism in Di-, Tri-, & Polyenes
• Total # of cis-trans isomers possible = 2n n = # of double bond
Double bond C2 – C 3 C4 – C 5 trans trans cis trans cis trans cis cis

2,4-heptadiene

What is the correct systematic name for the following? Br

• 1-bromo-2-hexene • 6-bromo-4-hexene • cis-1-bromo-2hexene • trans-1-bromo-2hexene

Alkenes: E/Z System
For more than two substituents the cis/trans, the E/Z system is used.

Alkenes: E/Z System
I H3C H F
H C O H H C C H
path goes to C, not H comparison stops here

H3C H

CH2 OH CH2 CH3
path goes to O, not H

(E)-3-fluoro-2-iodo-2-propene

Alkenes: E/Z System
C H

H H3C

CH CH2 CH2 CH3

CH CH2

C C C H H

H H CH2 CH3 C C H H H

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