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    Organic Chemistry Questions 3

    Uploaded by

    Ram Krishna
    This document is a practice exam for a CHEM 281 final. It consists of 12 pages including multiple choice and free response questions testing organic chemistry concepts. The exam covers reaction mechanisms, naming organic compounds, predicting products, acid-base properties and stereochemistry. Students are permitted to use molecular models for the bonus question at the end of the exam.

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    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd

    Organic Chemistry Questions 3

    Uploaded by

    Ram Krishna
    571 views12 pages
    This document is a practice exam for a CHEM 281 final. It consists of 12 pages including multiple choice and free response questions testing organic chemistry concepts. The exam covers reaction mechanisms, naming organic compounds, predicting products, acid-base properties and stereochemistry. Students are permitted to use molecular models for the bonus question at the end of the exam.

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    This document is a practice exam for a CHEM 281 final. It consists of 12 pages including multiple choice and free response questions testing organic chemistry concepts. The exam covers reaction mechanisms, naming organic compounds, predicting products, acid-base properties and stereochemistry. Students are permitted to use molecular models for the bonus question at the end of the exam.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    571 views12 pages

    Organic Chemistry Questions 3

    Uploaded by

    Ram Krishna
    This document is a practice exam for a CHEM 281 final. It consists of 12 pages including multiple choice and free response questions testing organic chemistry concepts. The exam covers reaction mechanisms, naming organic compounds, predicting products, acid-base properties and stereochemistry. Students are permitted to use molecular models for the bonus question at the end of the exam.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
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    You are on page 1of 12

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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)

    Spring XXXX Final Exam

    CHEM 281

    Page

    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)

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    11

    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

    Spring XXXX Final Exam

    CHEM 281

    Page

    12

    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

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