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Organic Chem Exam 3 Practice Answers for Chem 12B at Laney College, Spring 2013, Lecture notes of Stereochemistry

Pennsylvania State University - Berks Stereochemistry

The answers to Exam 3 practice questions for Organic Chemistry 12B (L1/L1L) students at Laney College during the Spring 2013 semester. The questions cover various topics such as IUPAC names, reasons for reactivity, mechanisms, starting materials, equilibria, synthetic transformations, and spectroscopic data interpretation.

What you will learn

Why are aldehydes more reactive than ketones in nucleophilic addition reactions? Provide two reasons. (10 points)
What are the IUPAC names for the given compounds, considering stereochemistry where appropriate? (20 points)

Typology: Lecture notes

2021/2022

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ORGANIC CHEMISTRY SPRING 2013, LANEY COLLEGE

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT

Exam 3 practice exam, answers Page 1 of 9

Answer Key

1. Provide IUPAC names for the following compounds (don’t forget stereochemistry where appropriate).

(20 points)

Partial preview of the text

Download Organic Chem Exam 3 Practice Answers for Chem 12B at Laney College, Spring 2013 and more Lecture notes Stereochemistry in PDF only on Docsity!

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3 practice exam, answers Page 1 of 9

Answer Key

Provide IUPAC names for the following compounds (don’t forget stereochemistry where appropriate). (20 points)

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3 practice exam, answers Page 2 of 9

Suggest two reasons why aldehydes are more reactive than ketones with regard to nucleophilic addition reactions? (10 points)
Show the complete mechanism for the following reaction (be sure to show all electron pushing). Also, show which steps are expected to be fast and which ones are slow. (15 points)

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3 practice exam, answers Page 4 of 9

Show the product (or products) produced or the reagents needed for the following synthetic transformations. (25 points)

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3 practice exam, answers Page 5 of 9

Which carboxylic acid shown below is more acidic? Clearly explain why. (10 points)
Suggest a synthetic scheme to convert the compound on the left to the compound on the right. (10 points)

EXTRA CREDIT Provide IUPAC names for the starting material and the product. (10 EC points)

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3 practice exam, answers Page 7 of 9

Show a starting material and the required reagents to obtain the product shown below. Also, provide an IUPAC name for the product.

(15 points)

The included spectra are for a compound with molecular formula C 6 H 10 O 5. In the 1 H NMR spectrum, subsequent addition of D 2 O resulted in the disappearance of the peak at ~3.5 ppm. Show the structure of this compound and for full credit assign the spectroscopic data – i.e., chemical shifts to each type of carbon and proton, IR frequencies, and mass spec. fragments. (15 points) EXTRA CREDIT explain the splitting pattern at 2.8 ppm in the 1 H NMR spectrum. (5 EC points)

CHEM 12B (L1/L1L) INSTRUCTOR: S. CORLETT Exam 3 practice exam, answers Page 8 of 9

Mass spectrum (M+^ = 162 m/z )

(^1) H and 13 C NMR are attached but expanded views of the 1 H NMR are below.

Organic Chem Exam 3 Practice Answers for Chem 12B at Laney College, Spring 2013, Lecture notes of Stereochemistry

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Partial preview of the text

Download Organic Chem Exam 3 Practice Answers for Chem 12B at Laney College, Spring 2013 and more Lecture notes Stereochemistry in PDF only on Docsity!