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CHEM 244 - Organic Chemistry II
Worksheet “Zero” (CHEM 243 Review)
The purpose of this worksheet is to review a few key concepts from CHEM 243, Organic Chemistry I. The
strategies you use to solve these problems will be essential for solving related problems in Organic Chemistry
II. Here are your goals in completing this worksheet:
• To complete this worksheet you will work with other students in class, along with help from Dr. Brush
and the Peer Leaders. It is also expected that you will work on your own outside of class.
• You may want to watch the “Mechanism Review” video on the class web page.
• Review the “Substitution/Elimination Guide” attached to the end of this worksheet.
• As needed, review lecture videos from CHEM 243.
• Make a list of any questions you have, and make sure that these get answered! The Peer Leaders and I
love being asked questions! You can continue asking us questions next week.
• You will not turn this worksheet in. However, your target date for completion is Friday, January 28.
• To get credit for this work, you will need to click this link and complete a class survey no later than
5:00 pm on Friday, January 28. DON’T FORGET!!! By completing this survey you will earn 50 points
that will be “Banked” and used to replace your lowest Group Quiz grade.
PART I. Read the Syllabus. In the survey you will need to confirm that you have read the class syllabus and
understand the expectations for this course.
PART II. Class Project. As part of our normal class work we will explore the problem of global warming,
understand the challenges of institutionalized environmental racism, and learn how green chemistry can
contribute to reducing the impacts of greenhouse gases through carbon capture. As we learn new concepts in
organic chemistry, we will apply these concepts to understand the background chemistry behind carbon capture.
This project will focus on the chemistry behind the capture of carbon dioxide, and the reactions of CO2.
(a) In the box below, answer the following questions related to bonding and structure in CO2:
• Draw the best Lewis Structure for CO2
• Include all relevant lone pairs
• Indicate the hybridization (sp, sp2, sp3) of each atom
• What is the molecular geometry of the carbon atom?
• Total number of sigma covalent bonds _____________
• Total number of pi covalent bonds ______________
(b) CO2 is formed in the combustion of fossil fuels. The combustion reaction of a hydrocarbon is given below.
Put the proper coefficients in the boxes to balance this equation.
(c) Together, we will explore the following topics as part of this project. Think about these terms and working
with your group (or by yourself) write down what they mean to you. If you aren’t sure, that is ok as we will
learn about these terms together.
UN Sustainable Development Goals
Global warming
Greenhouse gases
Carbon capture
Environmental racism
Green chemistry
PART II. Review Questions.
(1) Are the following pairs of compounds related as:
Identical Constitutional Isomers Enantiomers Diastereomers
(2) Formal Charge of an atom. Assign the proper Formal Charge to each circled atom in the molecules
drawn below. You may assume that all relevant lone electron pairs are included.
(3) Stereochemical Configurations. Assign the
correct R or S configuration to the labeled atoms
(a-e) in the molecule drawn at the right. If the
labeled atom is NOT a chiral carbon, write
“achiral”.
(a) __________ (b) __________ (c) __________ (d) __________ (e) __________
(4) Nomenclature. If a name is given, draw the correct chemical structure. If a structure is given, give the
IUPAC name.
(a)
(b) (3R, 4R)-1,3-dichloro-4-isopropyl heptane
(5) Reactions. Complete the reactions shown below by drawing the structure of the major, neutral organic
products. Watch your stereochemistry! You do NOT need to balance these reactions. You can find the
Substitution/Elimination Guide attached to this worksheet.
(6) Mechanisms. On a separate sheet of paper, write a complete mechanism that explains the formation of all
products for each of the balanced net reactions shown below. You MUST use the following format: (1) a series
of numbered, balanced chemical equations, and (2) curved arrows to show electron pair movement. Be sure to
watch the Mechanism Review video on the class web page before attempting these problems.
(a) SN1 Substitution (3 steps):
(b) Intramolecular
SN1 Reaction (3 steps):
(c) Acid-Catalyzed Electrophilic Addition
of Water to an Alkene (3 steps).
DON’T FORGET!!! To get credit for this work, you will need to click this link and complete a class survey
no later than 5:00 pm on Friday, January 28. By completing this survey you will earn 50 points that will be
“Banked” and used to replace your lowest Group Quiz grade.
(a) SN1 Substitution (3 steps):
(b) Intramolecular
SN1 Reaction (3 steps):
(c) Acid-Catalyzed Electrophilic Addition
of Water to an Alkene (3 steps).
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