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  • Organicchemistry2jasperse Web 1 Mechanism Practice Answorganicchemistry2jasperse

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    The document contains 17 organic chemistry problems involving reactions of alcohols, ketones, aldehydes, esters, epoxides, and Grignard reagents. The problems require drawing out the step-by-step mechanisms for reactions such as additions, eliminations, protonations, and reductions. Key reactions involve Grignard additions to carbonyl groups followed by protonation, reductions of carbonyls using LiAlH4 or NaBH4, and reactions of Grignard reagents or reducing agents with esters and cyclic esters.

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    The document contains 17 organic chemistry problems involving reactions of alcohols, ketones, aldehydes, esters, epoxides, and Grignard reagents. The problems require drawing out the step-by-step mechanisms for reactions such as additions, eliminations, protonations, and reductions. Key reactions involve Grignard additions to carbonyl groups followed by protonation, reductions of carbonyls using LiAlH4 or NaBH4, and reactions of Grignard reagents or reducing agents with esters and cyclic esters.

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    © All Rights Reserved
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    5 views5 pages

    Organicchemistry2jasperse Web 1 Mechanism Practice Answorganicchemistry2jasperse

    Uploaded by

    qwertymqwerty3330
    The document contains 17 organic chemistry problems involving reactions of alcohols, ketones, aldehydes, esters, epoxides, and Grignard reagents. The problems require drawing out the step-by-step mechanisms for reactions such as additions, eliminations, protonations, and reductions. Key reactions involve Grignard additions to carbonyl groups followed by protonation, reductions of carbonyls using LiAlH4 or NaBH4, and reactions of Grignard reagents or reducing agents with esters and cyclic esters.

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    © All Rights Reserved
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    of 5

    Organic

     Chemistry  2    Jasperse     Test  1,  Alcohol  Chemistry  


     
    T Draw  Mechanisms  for  the  Following  Reactions  
     
    RMgBr + Ketone
    1. OH
    1. Addition O MgBr
    2. Protonation
    1. 2. H+  
     
     
     
     
    RMgBr + Ketone 1.
    MgBr
    1. Addition
    2. Protonation O OH
    2. H+
    2.  
     
     
     
     
    T RMgBr + Aldehyde OH
    O 1.
    1. Addition MgBr
    2. Protonation H
    2. H+
    3.  
     
     
     
     
    O
    RMgBr + Aldehyde OH
    1. H
    1. Addition
    MgBr
    2. Protonation
    2. H+
    4.  
     
     
     
    T
     
    RMgBr + Epoxide O
    1.
    1. Addition OH
    MgBr
    2. Protonation
    2. H+
    5.  
     
     
     
     
    O
    1.
    BrMg HO
    T
    2. H+
    6.  
     
    RMgBr + Epoxide
    1. Addition  
     
    2. Protonation
     
     
    1. LiAlH4
    O OH

    2. H+
    7.  
     
    Ketone + LiAlH4
    1. Addition  
     
    2. Protonation
     
    NaBH4, CH3OH

    O
    8. OH  
     
    Ketone + NaBH4
    T
    1. Addition  
     
    2. Protonation
     
     
    O NaBH4, CH3OH HO

    9.  
     
    Ketone + NaBH4
    1. Addition  
     
    2. Protonation
     
     
    1. OH
    O (excess)
    MgBr
    O
    2. H+
    10.  
    T  
    RMgBr + Ester
     
    1. Addition
     
    2. Elimination
     
    3. Addition
     
    4. Protonation
       
    1. OH
    O (excess)
    MgBr
    T O
    2. H+
    11.  
     
    RMgBr + Ester
     
    1. Addition
     
    2. Elimination
     
    3. Addition
     
    4. Protonation
     
     
     
     
    1.
    MgBr (excess) OH
    O
    OH
    2. H+
    12. O  
     
    RMgBr + Cyclic
     
    Ester
     
    1. Addition
     
    T 2. Elimination
     
    3. Addition
     
    4. Double  
    Protonation
     
    O
    1. OH
    O MgBr

    OH
    2. H+
    13.  
     
    RMgBr + Cyclic
    Ester  
     
    1. Addition
     
    2. Elimination
     
    3. Addition
     
    4. Double  
    Protonation
     
    T 1. LiAlH4
    O OH
    O
    14. 2. H+  
     
    LiAlH4 + Ester
     
    1. Addition
     
    2. Elimination
     
    3. Addition
       
    4. Protonation
    O 1. LiAlH4 OH
    CH3
    O
    T
    2. H+
    15.  
     
    LiAlH4 + Ester
     
    1. Addition
     
    2. Elimination
     
    3. Addition
     
    4. Protonation LiAlH4 + Cyclic
     
    1. LiAlH4 Ester
    O O OH
    1. Addition
    HO 2. Elimination
    2. H+ 3. Addition
    16.  
      4. Double
      Protonation
     
     
    O
    1. LiAlH4 OH LiAlH4 + Cyclic
    O HO Ester
    1. Addition
    T 2. H+
    17.   2. Elimination
      3. Addition
     
    4. Double
     
    Protonation
     
    OH Br
    HBr
    Tert Alcohol + HX
    18.   to RX
      1. Protonate
      2. Loss of H2O
      3. Add halide
     
     
    HCl
    Tert Alcohol + HX
    to RX
    19. OH Cl   1. Protonate
    T   2. Loss of H2O
      3. Add halide
     
      Tert Alcohol + HX
    HBr to RX
    OH 1. Protonate
    20. Br   2. Loss of H2O
     
      3. Add halide
     
     
     

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