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).