LAST NAME:

FIRST NAME:

UTEID:
Instructions This exam will be closed book. No notes, books, calculators, or molecular models will be allowed. The exam will be comprised of two distinct parts: Part I will consist of a series of multiple choice questions. Your answers to these questions must be submitted on a Scantron bubble sheet. The answer sheet will be provided for you, but you will need your own #2 pencil(s). Only answers marked on the bubble sheet will be graded. Answers to Part I questions marked on the exam itself cannot not be graded. No re-grades will be possible on Part I of the exam. Part II consists of questions for which you will need to write out your answers, using structures and/or words. This part of the exam will be hand-graded. Answers for the Part II questions that are written in pencil will not be eligible for re-grades. Answers written in pencil with ink overlay will not be eligible for re-grades. If you use a pen to answer the Part II questions, only blue or black ink is acceptable. Answers written in red ink cannot be graded. 1. You must have your valid UT ID card (or other government-issued ID) with you. You will need to show it to the proctors when you turn in your exam. 2. Chapter 4 of the Universitys General Information catalog outlines this universitys policies regarding exams, as well as other quizzes administered during the semester. Specifically, students are expected to remain in the exam room until a test is completed. These policies will be strictly enforced, with no exceptions. You may not leave the room for any reason until you are ready to turn in your exam. If you wish to leave the room, you will need to turn in your exam to the proctors, and you will not be allowed to return. Please, plan accordingly by using the rest room before the exam starts.

CH 328 N Exam III

Question 1 2 3 4 5 6 Section II Section I Raw Total

Value 14 12 18 18 18 10 90 60 150

Score

Grade

ID: A

CH328N_Exam 3 Answer Section

MULTIPLE CHOICE 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: ANS: B A C D B A B C A B B B D B D PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: PTS: 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4

CH 328 N EXAM #3
PART 2: Free Style Answer Format

UTEID

KEY

(90 pts in this section)

1) Multistep synthesis. Provide the products for the following reactions. Be sure to include any stereo or regiochemistry if necessary. (14 pts)

OR
OCH3

O OCH3

1) CH3CH2CH2Br 2) H2O
OCH3

LDA THF -78o C

OCH3 O O O O OCH3

Draw the correct enolate

NaOCH3 CH3OH
OCH3 OCH3

1) CH3CO2CH3 2) H2O

OR

Draw the correct enolate 1) NaOCH3/CH3OH 2) PhCH2Br

O OH CH2Ph

O OCH3 CH2Ph

1) NaOH 2) H3O
+

CH2Ph

CH 328 N EXAM #3

UTEID

KEY

2) Diels Alder Reactions: Provide the cycloadducts for the following reactions. You must include the correct stereochemistry. (12 pts)

O H O

O O

H O O

Must show cis

CO2Et CO2Et CO2Et CO2Et

CO2Et

CO2Et

Must show cis

CO2Et CN EtO2C NC CN CO2Et

CN

CO2Et

Must show trans

Must show trans

CH 328 N EXAM #3

UTEID

KEY

3) Mechanism THE Robinson Ring annulation: Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. Use hydroxide and water whenever necessary. Draw methylvinyl ketone in the right box & show how it is connected. (18 pts)

O dehydrate OH

OH

OH O

H deprotonate proton transfer O O H OH O O

make-a-bond

H int: these are C--C bond f orming reactions

make-a-bond

O H2C O

OH

OH H

proton transfer

O H2C O

deprotonate

10

CH 328 N EXAM #3

UTEID

KEY

4) Reactions: Provide the product from each reaction. Be sure to include any stereo or regiochemistry if necessary. (18 pt)

O CO2CH3 OH O CO2CH3 OH 1) Br2 /HOAc 2) KOtBu 1) LDA 2) CH3CHO 3) H2O CO2CH3

O CO2CH3

NaBH4

1) NaOH 2) H3O+ 3)

1) 3 eq CH3MgBr 2) H3O+ 1) LiAlH4 2) H3O+

OH OH

OH CH2OH

11

CH 328 N EXAM #3

UTEID

KEY

5) Texas two step: Each of these problems are two step synthesis of a product. In the boxes around the arrows, provide the reagents for the reaction; note that a hydrolysis step (e.g. to finish a Grignard reaction) may be required. In the rounded rectangle, draw the structure of the compound from the first reaction. (6 pts per scheme) Scheme 1:

Scheme 2:

1) O3 2) Me2S or NaHSO3
CHO

NaOH;

Scheme 3:

12

CH 328 N EXAM #3

UTEID

KEY

6) Resonance: p-nitro phenol and m-nitro phenol are both acidic compounds, but one isomer is more acidic than the other. a) Draw the various resonance structures for each phenoxide anions. b) Predict which isomer is the more acidic and use the resonance structures to support your rationale. (10 pts) Draw the family of resonance structures for the p-nitrophenoxide:
O O O O O

NO2

NO2

NO2 O

N O O

N O

This resonance structure show the stabilizing eff ect of the nitro group at the para position pKa (p-nitrophenol)= 7.2 Stronger acid than m isomer Draw the family of resonance structures for the m-nitrophenoxide:
O O O O

NO2

NO2

NO2

NO2

This group of resonance structures shows that the nitro group has less stabilizing influence on the anion and therefore a lesser ef fect upon the acidity.

pKa (m-nitrophenol)= 8.4 Weaker acid than p isomer

END OF EXAM SECTION

13