Term
| Methylene is the simplest of the __________: uncharged, reactive intermediates that have a __________ atom with two bonds and two nonbonding electrons. |
|
Definition
|
|
Term
| Like __________, methylene is a potent electrophile because it has an unfilled octet and adds to the electron-rich __________ bond of an alkene to form a cyclopropane. |
|
Definition
|
|
Term
| Heating or photolysis of __________ gives nitrogen gas and methylene. |
|
Definition
|
|
Term
Two difficulties arrive when adding __________ to double bonds:
First, it is extremely toxic and explosive.
Second, __________ generated from diazomethane is so reactive that it inserts into C-H bonds as well as C=C bonds. |
|
Definition
1) Diazomethane
2) Methylene |
|
|
Term
Two DuPont chemists discovered a reagent that converts alkenes to __________ in better yields than diazomethane with fewer side reactions.
The __________-__________ reaction is one of the best ways of making cyclopropanes. |
|
Definition
1) Cyclopropanes
2) Simmons-Smith |
|
|
Term
The Simmons-Smith reagent is produced by adding __________ __________ to the "zinc-copper couple" (__________ dust that has been activated with an impurity of __________) .
The reagent probably resembles __________ __________ __________, ICH2ZnI.
This kind of reagent is called a __________ because it reacts much like a carbene but does not actually contain a divalent carbon atom. |
|
Definition
1) Methylene iodide
2) Zinc
3) Copper
4) Iodomethyl zinc iodide
5) Carbenoid |
|
|
Term
Carbenes are also formed by reactions of halogenated compounds with __________.
If a carbon atom has bonds to at least one __________ and to enough halogen atoms to make the hydrogens slightly __________, it may be possible to form a __________. |
|
Definition
1) Bases
2) Hydrogen
3) Acidic
4) Carbene |
|
|
Term
An __________ __________ occurs when a hydrogen and halogen are lost from the same carbon.
The more common __________ __________ occur when a hydrogen and halogen are lost from adjacent carbons. |
|
Definition
1) Alpha elimination
2) Beta elimination |
|
|
