(CHE 005): Organic Chemistry Laboratory

Student Activity Sheet Module #5

Name:______________________________________________ Class Number:_____________

Section:_______________________ Schedule:_____________ Date:____________________

Lesson title: ISOMERISM( Part 2) - STEREOISOMERISM Materials:

Lesson Objectives: SAS
At the end of this module, I should be able to: References:
1. Identify properties of geometric isomers. https://
2. Delineate ” cis” from “trans” isomerism. courses.lumenlearning.com/
boundless-chemistry/chapter/
3. Build and model “cis’ isomers and ” trans” isomers.
functional-group-names-properties-
and-reactions/

https://
www.masterorganicchemistry.com/
2018/09/10/types-of-isomers/

https://www.youtube.com/watch?
v=StyqGmtYF7A&t=281s

Productivity Tip:
Use words that will remind you of the meaning of the technical terms. For “cis” isomers for example , you
think of sis( as in sisters who are on the same side) and for ‘trans’ isomers, you think of transfer because
they are away from each other.

A. LESSON PREVIEW/REVIEW

1) Introduction
Hi flames! Prof. Cosue here once again. Can you describe these icons in one word. Make sure that the
word is related to the previous lesson.

Use that word in one sentence to describe isomerism. Please share with your chat buddy.

Activity 1: What I Know Chart, Part 1

What do you have in mind when we say stereoisomerism? Try answering the questions below by
writing your ideas under the first column What I Know. It’s okay if you write key words or phrases that
you think are related to the questions.

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Student Activity Sheet Module #5

What I Know Questions: What I Learned (Activity 4)

What is stereoisomerism?

How does it differ from

structural isomerism?
What are examples?

B. MAIN LESSON

1) Activity 2: Content Notes

Isomers are two or more molecules that share the same molecular formula. Connect the molecules below
that are isomers. And what kind of isomers are they?

Isomers divide neatly in to two categories: constitutional isomers (different connectivity) and stereoisomers
(same connectivity, different arrangement in space). So what does that actually mean?

Stereoisomerism
This type of isomerism arises in compounds having the same chemical formula but different orientations of the
atoms belonging to the molecule in three-dimensional space. The compounds that exhibit stereoisomerism are
often referred to as stereoisomers. This phenomenon can be further categorized into two subtypes.

Geometric Isomerism

 It is popularly known as cis-trans isomerism. The “cis” and the “trans” are parts of the name.
 These isomers have different spatial arrangements of atoms in three-dimensional space.
 This only occurs when:
restricted rotation (often involving a carbon-carbon double bond for introductory purposes); and
two different groups on the left-hand end of the bond and two different groups on the right-hand
end. It doesn't matter whether the left-hand groups are the same as the right-hand ones or not.

“Trans” isomers are those with similar groups arranged in opposite direction. The
Isomers with similar groups on the same side are called as “cis” isomers.

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 (CHE 005): Organic Chemistry Laboratory
Student Activity Sheet Module #5

Take a look at the molecules below where the substituents are circled with red ink. Notice that in the first
two, the substituents are on the same side – where both are up in the first and both are down in the second.
These are examples of “cis” isomers. Due to allowable rotation of the sigma bond ( single bond), the first
and the second are the same.
In the third molecule however, the substituents are opposite each other so they are the “trans” isomers.

ubstituents are on the same

“trans”- red and blue substituents are on opposite sides

The
most likely example of geometric isomerism you will meet at an introductory level is but-2-ene. In one case, the
CH3 groups are on opposite sides of the double bond, and in the other case they are on the same side.

2) Activity 3: Skill Building Activities

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 (CHE 005): Organic Chemistry Laboratory
Student Activity Sheet Module #5

A. The reading shows the two geometric isomers of 2-butene, C4H8. There are two other alkenes
with the formula C4H8. Draw their structures and determine whether they too can exist
in cis and trans forms.

B. Which of the following can have cis/trans isomers? Draw their isomers.
(CH3CH2)CH=CH2, (CH3CH2)2C=CHCH3, (CH3CH2)CH=CHCH3

C. One of these molecules has geometric isomers and the other one doesn't. Explain the
difference.

Activity 4: What I Know Chart, Part 2

Patience truly pays off! Keep it up! It’s time to answer the questions in the What I Know chart in Activity
1. Log in your answers in the table.

Activity 5: Check for Understanding

MULTIPLE CHOICE: Circle the letter of the best answer ( 1 point each).
1. For which of the compounds below are cis-trans isomers possible?
CH3CH=CH2 CH3CH=CHCH2CH3 CH3CH=CHCH3
(1) (2) (3)
(a) only 2 (b) both 1 and 2
(c) both 2 and 3 (d) all three (e) only 3

2. Which of the following does NOT exhibit geometric isomerism? (Hint: draw them!)
(a) 4-octene (b) 2-pentene (c) 3-hexene
(d) 2-hexene (e) 1-hexene

3. The number of pi bonds in the molecule shown below is ______

CH3CH=CHCH2C CH

(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

4. The relationship of the following two structures is____

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 (CHE 005): Organic Chemistry Laboratory
Student Activity Sheet Module #5

H3C Br Br Br
C C C C
Br CH3 H3C CH3

(a) structural isomers (b) geometric isomers (c) the same

(d) not isomeric (e) conformational isomers

5. Which of the following does not allow free rotation?

(a) single bond (b) ring structure
© pi bond (d) both b and c

WRAP UP LESSON

You are incredibly smart! Shade the number of the module that you finished.

This particular topic is difficult to

follow___________________________________________________________________________________

________________________________________________________________________________________
________________________________________________________________________________________

This technique is illuminating :

________________________________________________________________________________________
________________________________________________________________________________________

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FAQs

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 (CHE 005): Organic Chemistry Laboratory
Student Activity Sheet Module #5

KEY TO CORRECTIONS

Introduction: Connectivity
Answers to Skill-Building Exercises

Answers:

A.

2-methylpropene does not have cis and trans forms.

1-butene does not have cis and trans forms.

B.

a.

The one with double bond exhibits geometric

isomerism as it has a restricted rotation unlike
the first with sigma bond.

ANSWERS TO CHECK FOR UNDERSTANDING

MULTIPLE CHOICE
1. c 3. A 5. d
2. e 4. c

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