CHEM 281 Prectice for Final Exam

Spring semester XXXX Instructor: Dr. Peggy Paduraru

Student Signature
Please, READ THE QUESTIONS COMPLETELY AND CAREFULLY Clearly mark the answers in the multiple choice sets:

or

Your exam consists of 12

printed pages including this one. The final page of this exam includes a bonus question and you are permitted to use molecular models.

Question 1 (18) 2 (16) 3 (4) 4 (10) 5 (19) 6 (3) 7 (12) 8 (8) 9 (10) Total (100) 1 1 1 1 1 1 1 1 1

Mark 1 1 1 1 1 1 1 1 1 1

10 (5) - BONUS 1 Total

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1. Clearly indicate the right answer for the following multiple choice questions (A to I). (2 marks
each)

A. What is the activation energy for the reaction B ? A in the following diagram?

B. Which one of the following alkyl halides undergoes E1 reactions with the fastest rate?

CH3CHCH3
F

CH3CHCH3
Cl

CH3CHCH3
Br

CH3CHCH3
I

CH3I

C. Which of the following is the best method for preparing CH3Br?

CH3OH + Br CH3OH + HBr

CH3OH + Br2 CH3OH + NaBr

CH3OH + Br+

D. Which of the following is the most stable cation?

CH3 H3CC CH2 H3C C CH3 CH3 C CH3

CH3

E. What is the name of the major organic product of the following reaction?
CH2=CHC(CH3)3 3,3-dimethyl-1-butanol 2,3-dimethyl-1-butanol H+, H2O 2,3-dimethyl-2-butanol

3,3-dimethyl-2-butanol 4-methyl-2-pentanol

F. Which of the following is not a nucleophile?

Br

FeBr3

NH3

CH3 OCH3

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G. Which of the following is the best nucleophile in water?

CH3SCH3

CH3OCH3

Cl

Br

H. How many proton NMR single ts will 2-bromo-3-methyl-2-butene exhibit?

G. What are the major products from the following reaction?

O H2 C

HI

I
+

CH2OH

OH
+

CH2I

OCH2I
+

OH

I
+

OCH2OH

H. Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

water + dilute acid water + concentrated acid

oxymercuration-reduction hydroboration-oxidation

I. Which of the following statements about propene, CH3CH=CH2 is correct?

all nine atoms lie in the same plane the compound has a cis and a trans isomer all the atoms are sp2 hybridized

it generally acts as a Lewis acid there is a total of eight sigma bonds

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2. Predict the major products of the following reactions. Include stereochemistry where appropriate. (2 marks each)

(a)

HCl

(b)

Br 2 CCl4

(c)

1. BH3, THF 2. H2O2, -OH

Br2 (d) CH3OH

(e)

H2 Pt

PhCO3H (f)

(g)

H 2O H+

(h)

1. Hg(OAc) 2, H 2O 2. NaBH 4

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3. Provide a detailed, step-by-step mechanism for the reaction shown below. (4 marks)
Br HO Br2 O + HBr

4. Consider the reaction shown below.

CH2CH 3 Cl

NaOCH2CH3 CH3CH2OH
CH 3

H 3C

CH3

a) Will it proceed by substitution of elimination? What factors determine the most likely mechanism? (2 marks)

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b) Give the systematic name for the starting material (A). (3 marks)

Name: c) Draw two stereoisomers of compound A and specify their relationship to compound A. (2
marks)

Stereoisomer 1

Stereoisomer 2

d) Write the expected product and the mechanism by which it forms. (3 marks)

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5. For the following questions (a to e) consider the scheme below as well as the additional facts.
OH A H2SO4 heat HCl H2 O B + C

Facts: - the 1 H NMR of compounds B and C is provided below: B: C: 1.01 (d, 6H), 1.71 (d, 3H), 1.87 (m, 1H), 1.92 (m, 2H), 5.48 (m, 1H), 5.52 (m, 1H) 1.06 (t, 3H), 1.11 (d, 6H), 2.0 (m, 2H), 2.52 (m, 1H), 5.47 (m, 1H), 5.50 (m, 1H) - compounds A and E are constitutional isomers a. Identify structures B to E in the boxes below. (6 marks: 1.5 marks each)
B C

b. Draw two stereoisomers of compound B and name one of them. (2 marks)

stereoisomer 1 stereoisomer 2

Name

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c. Write a detailed mechanism to account for the transformation below: (4 marks)

H2O

d. Draw a reaction coordinate diagram for the transformation above (D E). Please label transition state(s) as TS, the rate determining step as RDS and indicate what intermediates (if any) are involved. Also, on the diagram indicate G and G0. (4 marks)

Energy

Progress of reaction

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e. Starting with compound C identified from the scheme above, synthesize 3 alcohols which are structural isomers. (Fill in the structure of compound C, the three reaction conditions and the structure of the three alcohols) (3 marks)

6. Rank the following compounds according to their acidity (3 marks)

HO H3C A B CH3 CH3 CH3 C D OH CO 2H

Most Acidic

Least acidic

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10

7. In the box above each reaction arrow, please fill in the reagents that would be required to effect the desired transformation. (12 marks: 2 marks each box)

a) OH

b)

c) OH

d) Br

8. Please provide the necessary reagents and conditions to effect the following transformations (more than one step is necessary for each transformation). (8 marks)
O H

a)
Br

b)

HC

CH

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9. Answer the following questions considering the structures A, B and C below.

OCH3 O OH OCH3 OH

A
A B

B
and A C

a) Show the reagents/conditions for the transformations. (4 marks)

b) Is an equimolar mixture of B and C chiral? (circle the one that applies) (2 marks)

YES
c) Draw the enantiomer or compound A. (2 marks)

NO

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d) Compare the boiling points of compounds A and C? Explain (2 marks)

10. BONUS QUESTION (5 marks) How would you accomplish the following transformation (more than one step might be necessary).
Br

Br