Scribd Logo
Upload

Welcome to Scribd!

  • 32 views

    Massachusetts Institute of Technology 5.12, Spring 2005: Problem Set #4

    Uploaded by

    Karthikeyan
    This document provides 10 problems related to organic chemistry reactions. The problems ask students to: 1) identify products of reactions; 2) determine starting materials and reagents to form given products; 3) draw reaction intermediates and show orbital overlap; 4) provide mechanisms for reactions including ozonolysis, halolactonization, and substitutions; and 5) determine stereochemistry of reaction products. Students must use their knowledge of reaction mechanisms and stereochemistry to solve each multi-part problem.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd

    Massachusetts Institute of Technology 5.12, Spring 2005: Problem Set #4

    Uploaded by

    Karthikeyan
    32 views9 pages
    This document provides 10 problems related to organic chemistry reactions. The problems ask students to: 1) identify products of reactions; 2) determine starting materials and reagents to form given products; 3) draw reaction intermediates and show orbital overlap; 4) provide mechanisms for reactions including ozonolysis, halolactonization, and substitutions; and 5) determine stereochemistry of reaction products. Students must use their knowledge of reaction mechanisms and stereochemistry to solve each multi-part problem.

    Original Title

    MIT IOC 4

    Copyright

    © © All Rights Reserved

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    This document provides 10 problems related to organic chemistry reactions. The problems ask students to: 1) identify products of reactions; 2) determine starting materials and reagents to form given products; 3) draw reaction intermediates and show orbital overlap; 4) provide mechanisms for reactions including ozonolysis, halolactonization, and substitutions; and 5) determine stereochemistry of reaction products. Students must use their knowledge of reaction mechanisms and stereochemistry to solve each multi-part problem.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    32 views9 pages

    Massachusetts Institute of Technology 5.12, Spring 2005: Problem Set #4

    Uploaded by

    Karthikeyan
    This document provides 10 problems related to organic chemistry reactions. The problems ask students to: 1) identify products of reactions; 2) determine starting materials and reagents to form given products; 3) draw reaction intermediates and show orbital overlap; 4) provide mechanisms for reactions including ozonolysis, halolactonization, and substitutions; and 5) determine stereochemistry of reaction products. Students must use their knowledge of reaction mechanisms and stereochemistry to solve each multi-part problem.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 9

    Massachusetts Institute of Technology 5.

    12, Spring 2005

    Problem Set #4
    Due: March 10, 4:00 pm

    1. Provide the product of each reaction shown below. Include stereochemistry.

    H2
    CH2I2
    Pd/C Cl2
    Zn(Cu)
    1. BH3, THF
    2. H2O2, NaOH
    RCO3H

    warm, conc. KMnO4 1. OsO4


    H3O+ 2. NaHSO3, H2O

    1. Hg(OAc)2, EtOH
    2. NaBH4 CHBr3, KOH

    1. O3
    HI 2. (CH3)2S
    Br2, H2O

    2. Provide the major product of each reaction.

    1. mCPBA
    2. NaOH

    1. BH3, THF H2, Pd/C


    2. H2O2, NaOH

    1. Hg(OAc)2, H2O
    2. NaBH4
    Br2

    3. Provide the best alkene starting material and reagents required to form each product.

    Br Br
    a) Br Br

    b)
    Cl Cl

    O O
    c)

    d)

    OH OH
    e)
    OH HO

    OH OH
    f)
    HO OH

    O
    H
    g)
    O

    3
    4. Provide all the possible products for the following reaction. Which product is
    more stable and why?

    HBr

    5. Provide all stereoisomers that result from the following reactions. For b-f, indicate if the
    products are optically active (C), optically inactive/racemic (R), or optically inactive/meso
    (M).

    1. O3
    a)
    2. H2O2, H2O

    CH2I2, Zn(Cu)
    b)

    Hint: build a model!

    c) Br2, H2O

    1. OsO4
    d)
    2. H2O2

    1. BH3, THF
    e)
    2. H2O2, NaOH

    f) Cl2

    5
    6. a) Draw the intermediate that results from the reaction of Cl2 with (E)-3-methyl-3-
    hexene. b) Show the initial orbital overlap for the second step of this reaction. c)
    Explain why the nucleophile attacks the more substituted atom in the second step by
    drawing transition states.

    7. Using what you know about the first step of ozonolysis, show the mechanism and
    product for the following reaction.

    H2C N N

    8. Lactones, or cyclic esters such as the starting material shown below, are prepared
    by halolactonization, an addition reaction to an alkene. The following lactonization is a
    key intermediate in the synthesis of prostaglandin PGF2a. Draw a stepwise mechanism
    for this addition reaction.

    OH O

    O I2 O
    NaHCO3
    OCH3 I OCH3
    OH OH

    9. Show the mechanism for each reaction. Ignore stereochemistry.

    HBr
    a) OCH3

    O HBr
    b) CH3
    O

    Cl2
    c) OH

    8
    10. Show the mechanism and major product for each reaction.

    HBr
    a)

    HBr
    b)

    You might also like