Orgo 8.11, 8.15b

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  1. __ is the simplest of the __: uncharged, reactive intermediates that have a carbon atom with two bonds and two nonbonding electrons. Like borane, __ is a potent __ because it has an __. It adds to the __ of an alkene to form a __.
    • methylene
    • carbenes
    • methylene
    • electrophile
    • unfilled octet
    • electron-rich pi bond
    • cyclopropane
  2. Heating or photolysis  of __ gives nitrogen gas and __.

    The __ generated from __ reacts with alkenes to form __, but __ is very toxic and explosive, and the __ generated is so reactive thta it forms many side proucts. A safer and more reliable way to make cyclopropanes is with the __
    • diazomethane
    • methylene
    • methylene
    • diazomethane
    • cyclopropanes
    • diazomethane
    • methylene
    • Simmons-Smith reagent
  3. The __ is made by adding methylene iodide to the "zinc-copper couple" (__ that has been activated with an impurity of copper). The reagent probably resembles iodomethyl zinc iodide. This kind of reagent is called a __ because it reacts much like a __, but it does not actually contain a __.
    • Simmons-Smith reagent
    • zinc dust
    • carbenoid
    • carbene
    • divalent carbon atom
  4. __ are also formed by reaections of halogenated compounds with bases. If a carbon atom has bonds to at least __ and to enough __ to mae the hydrogen __, it may be possible to form a __.
    • carbenes
    • one hydrogen
    • halongens
    • slightly acidic
    • carbene
  5. This dehydrohalogenation is called an __ because the hydrogen and the halogen are lost from the __ The more common dehydrohalogenations (to form alkenes) are called )) because the hydrogen and halogen are lost from adjacent carbon atoms
    • alpha elim
    • beta elim
  6. The products of the cyclopropanations do what?
    retain any cis or trans stereochemistry of reactants
  7. Like permanganate, ozone cleaves double bonds to give __ and __. HOwever, __ is milder, and both __ and __ can be recovered without further __.
    • ketones
    • aldehydes
    • ozonylsis
    • keetones 
    • aldehydes
    • oxidation
  8. __ is a high-energy form of oxygen produced when UV light or an electrical discharge passes through oxygen gas. UV light from the sun converts oxygen to ozone in the upper atmosphere. This __ shields the earth from some of the high energy UV radiation it would otherwise receive.
    • ozone
    • ozone layer
  9. __ has 142 kJ/mol of excess energy over oxygen, and it is much more reactive. __ reacts with an __ to form a cyclic compound called a __. The __ has two __ linkages, so it is quite unstable. It rearranges rapidly, even at low temperatures, to form an __.
    • ozone
    • primary ozonide or molozonide
    • molozonide
    • peroxy
    • ozonidde
  10. __ are not very stable, and they are rarely isolated. In most cases, they are immediately reduced by a mild reducing agent such as zinc or (more recently) dimethyl sulfide. The products of this reduction are __ and __.
    • ozonides
    • ketones 
    • aldehydes
  11. One of the most common uses of ozonolysis has been used for what?
    determining the positions of double bonds in alkenes

Card Set Information

Orgo 8.11, 8.15b
2013-11-24 16:40:51
CHM 201

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