Prepare for your exams
Get points
Guidelines and tips

Sell on Docsity

Log in Sign up

Prepare for your exams

Study with the several resources on Docsity

Earn points to download

Earn points by helping other students or get them with a premium plan

Guidelines and tips

Sell on Docsity

Log in Sign up

Prepare for your exams

Study with the several resources on Docsity

Find documents

Prepare for your exams with the study notes shared by other students like you on Docsity

Search Store documents

The best documents sold by students who completed their studies

Search through all study resources

Docsity AINEW

Summarize your documents, ask them questions, convert them into quizzes and concept maps

Explore questions

Clear up your doubts by reading the answers to questions asked by your fellow students

Earn points to download

Earn points by helping other students or get them with a premium plan

Share documents

20 Points

For each uploaded document

Answer questions

5 Points

For each given answer (max 1 per day)

All the ways to get free points

Get points immediately

Choose a premium plan with all the points you need

Study Opportunities

Choose your next study program

Get in touch with the best universities in the world. Search through thousands of universities and official partners

Community

Ask the community

Ask the community for help and clear up your study doubts

University Rankings

Discover the best universities in your country according to Docsity users

Free resources

Our save-the-student-ebooks!

Download our free guides on studying techniques, anxiety management strategies, and thesis advice from Docsity tutors

From our blog

Exams and Study

Go to the blog

Practice Exam 3 - Organic Chemistry - Fall 1999 | CHEM 345, Exams of Organic Chemistry

University of Wisconsin (UW) - Milwaukee Organic Chemistry

Material Type: Exam; Class: Organic Chemistry; Subject: Chemistry; University: University of Wisconsin - Milwaukee; Term: Fall 1999;

Typology: Exams

Pre 2010

Uploaded on 09/02/2009

koofers-user-aig-2 🇺🇸

5

(1)

10 documents

1 / 6

This page cannot be seen from the preview

Don't miss anything!

1

Last Name _____________________________ First Name _______________________________

Please Print. Please put your name on the back of the test also.

EXAM 3 ORGANIC CHEMISTRY 345

November 10, 1999 Schwabacher

Quiz scores so far

page 2. (23 points) Q4

page 3. (30 points) Q5

page 4. (18 points) Q6

page 5. (19 points) Q7

page 6. ________ (20 points) Q8

TOTAL (110 points)

Partial preview of the text

Download Practice Exam 3 - Organic Chemistry - Fall 1999 | CHEM 345 and more Exams Organic Chemistry in PDF only on Docsity!

Last Name _ First Name ___

Please Print. Please put your name on the back of the test also.

EXAM 3 ORGANIC CHEMISTRY 345

November 10, 1999 Schwabacher

Quiz scores so far

page 2. (23 points) Q

page 3. (30 points) Q

page 4. (18 points) Q

page 5. (19 points) Q

page 6. ________ (20 points) Q

TOTAL (110 points)

OH

O

I. (9 points) Nomenclature: Provide a structure for the given name.

A)

2,2-diethylmalonic acid

B)

methyl acetoacetate

C)

(S)-2-ethylhexanoyl chloride

II. (14 points)

reference HCl CH 3 CH 3

pKa = -7 0 5 11 16 19 25 40 60

Use the reference scale of pKa values above to assign an approximate pKa to each

molecule below. Your answer for each should be one of the 9 numbers from the scale,

so you can figure out the pKa values by knowing only the acidity order of these

compounds. There are no duplicates.

OH N H

O

O O O O

O

OH

O

H H

OH

O

F

F F

HN

IV. (18 points) Provide mechanisms for these reactions, showing all intermediates and all steps

including proton transfers. Show all lone pairs and formal charges. This time you

do not need to show all resonance forms.

A. (10 pts.)

B. (8 pts.) Write a mechanism. Your mechanism must show why this reaction proceeds

readily under mildly acidic conditions where ordinary secondary alcohols do not eliminate.

O

OH

O

OH H^2 O

cat. HCl

Practice Exam 3 - Organic Chemistry - Fall 1999 | CHEM 345, Exams of Organic Chemistry

Related documents

Partial preview of the text

Download Practice Exam 3 - Organic Chemistry - Fall 1999 | CHEM 345 and more Exams Organic Chemistry in PDF only on Docsity!

Last Name _____________________________ First Name _______________________________

Please Print. Please put your name on the back of the test also.

EXAM 3 ORGANIC CHEMISTRY 345

November 10, 1999 Schwabacher

Quiz scores so far

page 2. (23 points) Q

page 3. (30 points) Q

page 4. (18 points) Q

page 5. (19 points) Q

page 6. ________ (20 points) Q

TOTAL (110 points)

OH

O

I. (9 points) Nomenclature: Provide a structure for the given name.

A)

2,2-diethylmalonic acid

B)

methyl acetoacetate

C)

(S)-2-ethylhexanoyl chloride

II. (14 points)

reference HCl CH 3 CH 3

pKa = -7 0 5 11 16 19 25 40 60

Use the reference scale of pKa values above to assign an approximate pKa to each

molecule below. Your answer for each should be one of the 9 numbers from the scale,

so you can figure out the pKa values by knowing only the acidity order of these

compounds. There are no duplicates.

OH N H

O

O

O

O O O O

O

OH

O

H H

OH

O

F

F F

HN

IV. (18 points) Provide mechanisms for these reactions, showing all intermediates and all steps

including proton transfers. Show all lone pairs and formal charges. This time you

do not need to show all resonance forms.

A. (10 pts.)

B. (8 pts.) Write a mechanism. Your mechanism must show why this reaction proceeds

readily under mildly acidic conditions where ordinary secondary alcohols do not eliminate.

O

OH

O

OH H^2 O

OH

O

OH O

O

H 2 O

H 2 SO 4

CH 3 CH 2 OH

C. (10 pts.) Write a mechanism, showing all intermediates. Show the most significant

resonance form of each intermediate, but you need not show all resonance forms. Circle the

structure of the species present in the reaction at the end of the first step, before addition of

acid. Note that base is added in stoichiometric, not catalytic, amount.

V. A. (9 pts) Cross off the molecule(s) below that could not have been formed by an aldol

reaction. For each molecule below that could have been formed by an aldol

condensation or aldol dehydration, draw the stable precursor(s) of aldol condensation.

O O

O

O O

H H

O OH O O

OH

HO O

Last Name _ First Name ___