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 II

Question 1 2 3 4 5 6 7 Section II Section I Raw Total

Value 18 12 12 12 9 12 15 90 60 150

Score

Grade

UTID: ________________________

October 2013

CH328N-Exam II
Objective Test Section Identify the choice that best completes the statement or answers the question. There is only one correct answer; please carefully bubble your choice on the scantron sheet. (4pts. ea; 60 pts this section)
1. What is the best choice of reagent(s) to perform the following transformation?

a. b. c. d.

1. LiAlH4; 2. H3O+ NaH 1. NaBH4; 2. H2O H2, Pt

2. Which of the following carboxylic acids undergoes the most rapid thermal decarboxylation reaction?

a. b. c. d.

1 2 3 4

3. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

4. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

5. Which of the following is the best description of the mechanism of the reaction between a ketone and an amine to form an imine? a. concerted bimolecular substitution b. electrophilic addition followed by rearrangement c. elimination followed by nucleophilic addition d. nucleophilic addition followed by elimination

6. Which of the following compounds is the most acidic? (i.e has the lowest pKa)

a. b. c. d.

1 2 3 4

7. What of the following is the correct assignment of the classes of the following compounds?

a. b. c. d.

1 = ester; 2 = ester; 3 = imide 1 = ester; 2 = imide; 3 = amide 1 = lactone; 2 = ester; 3 = amide 1 = lactone; 2 = anhydride; 3 = imide

8. What is the approximate pKa value of acetic acid a. 2 b. 5 c. 15 d. 35 9. What is the major organic product obtained from the following reaction?

a. b. c. d.

2-pentanol pentane (E) 2-pentene 1-pentene

10. Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)? a. FCH2COOH > CH3COOH > F2CHCOOH b. CH3CH2OH > ClCH2COOH > BrCH2COOH c. CH3COOH > ClCH2COOH > CH3OH d. FCH2COOH > CH3COOH > CH3OH 11. What is the correct assignment of the names of the following aldehydes and ketones?

a. b. c. d.

1 = acetaldehyde; 2 = acetophenone; 3 = benzophenone 1 = acetaldehyde; 2 = acetone; 3 = acetophenone 1 = formaldehyde; 2 = acetaldehyde; 3 = acetone 1 = acetone; 2 = acetaldehyde; 3 = formaldehyde

12. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

13. What is the IUPAC name of the following compound?

a. b. c. d.

butyl isopropanoate pentanoyl isopropane isopropyloxybutanal isopropyl pentanoate

14. What is the major organic product obtained from the following reaction?

a. b. c. d.

1 2 3 4

15. What is the major organic product obtained from the following reaction?

a. b. c. d.

2-pentanol 2-pentanone (E)-3-penten-2-ol 4-hydroxy-2-pentanone

ID: A

CH328N-Exam II 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: D C B A D C D B A D C B D C A 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 #2
PART 2: Free Style Answer Format

UTEID

KEY

(90 pts in this section)

1) Texas two-step: Each of the following synthesis require sets of reagents and one intermediate. Place the correct reagents (there may be 2 or more) in the boxes, with the arrows and the intermediate compound in the rounded rectangle. (18 pts)

CH 328 N EXAM #2

UTEID

KEY

2) Mechanism: Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. (12 pts) O NH2OH H+ (cat)

N OH

O H
+

HO

H N H OH

NH2OH
Add a proton Make-a-bond

Intramolecular transfer of H from protonated amino alcohol

H3O+ H 2O N OH H N H 2O OH

Loss of water to form the imine

CH 328 N EXAM #2

UTEID

KEY

3) Transformations: Provide the product for each of the reactions below.. (12 pts)

O NNH OH Ph H Ph

OH H2CrO4 H2NNHPh LAH O

2 NH 3 H C 1) i /N 2 H 2)

HOCH2CH2OH NH2NH2 KOH; cat H+

CH3 HN O CH3 Ph H Ph O H

CH 328 N EXAM #2

UTEID

KEY

4) Mechanism: Provide a mechanism for the following transformation. Show all important flows of electrons, charges and intermediates. Where indicated, (in the structure-n-a- box)draw the intermediates. (12 pts)

H2O H3CO H OCH3 OH2

loose a proton
O CH3OH

add a proton break-a-bond

H H3CO OCH3 H H3CO OH

break-a-bond

add a proton

H3CO

CH3OH OH2

H H3CO

OH2 OH

H2O

make-a-bond

H H3CO OH

loose a proton

CH 328 N EXAM #2

UTEID

KEY

5) Grignard: Provide either the Grignard reagent or the carbonyl to synthesize 2-phenyl-2pentanol. (9 pts)

6) Multi-step synthesis: Provide the products for the following scheme. For full credit, you must show the correct regiochemistry. (12 pts)

10

CH 328 N EXAM #2

UTEID

KEY

7) Mechanism: The Wolff-Kishner reduction converts ketones to hydrocarbons. Provide a mechanism for the following example of this transformation. Show all important flows of electrons, charges and intermediates. (15 pts)

END OF EXAM SECTION

11