Orgo 10.7-10.9

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DesLee26
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253943
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Orgo 10.7-10.9
Updated:
2013-12-19 21:32:59
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CHM 202
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Organic,Chemistry
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  1. What were the previous alcohol syntheses?
    • 1) nucleophilic substitution on an alkyl halide
    • 2) acid-catalyzed hydration
    • 3) oxymercuration-demercuration
    • 4) hydroboration-oxidation
    • 5) dihydroxylation
    • 6) addition of acetylides to carbonyl compounds
  2. __ contain covalent bonds between carbon atoms and metal atoms. __ are useful because they have nucleophilic carbon atoms, in contrast to the electrophilic carbon atoms of alkyl halides. Most metals (M)  are more __ than carbon, and the C-M is __ with a __ on the metal and a __ on carbon.
    • organometallic compounds x2
    • electropositive
    • partial positive charge
    • partial negative charge
  3. __ are weakly acidic, and they are converted to __ by treatment with an unusually strong base, __. These __ are useful nucleophiles, reacting with alkyl halides and carbonyl compounds to form new carbon-carbon bonds.
    • terminal alkynes
    • sodium acetylides
    • sodium amide
    • sodium acetylides
  4. Most __ and __ are not acidic enough to be deprotonated by __, but they can be made into __ and __. These reagents are extremely __, providing some of our best ways of forming C-C bonds.
    • alkyl 
    • alkenyl groups
    • sodium amide
    • Grignard reagents
    • organolithium reagents
    • versatile
  5. __ of __ and __ are frequently used for the synthesis of alcohols. The __, of empirical formula R-Mg-X, are called __ . __ result from the reaction of an alkyl halide with __. This reaction is always carried out in a __, which is need to __ and __ the __ as it forms.
    • organometallic compounds
    • Li
    • Mg
    • organomagnesium halides
    • Grignard reagents x2
    • Mg metal
    • dry (anhydrous) ether solvent
    • solvate
    • stabilize
    • Grignard reagent
  6. The __ species in solution usually contains two, three, or four of the R-Mg-X units associated together with several molecules of the ether solvent. Diethyl ether is the most common solvent for these reactions, although other ethers are also used.
    Grignard reagent
  7. __ may be made from primary, secondary, and tertiary alkyl halides, as well as from __ and __. __ are the most reactive halides, followed by __ and __. __ generally do not react.
    • Grignard reagents
    • vinyl and aryl halides
    • alkyl iodies
    • bromides
    • chlorides
    • alkyl fluorides
  8. What is the order of reactivity?
    R-I > R-Br > R-Cl >> R-F
  9. Like Mg, Li reacts with __, __ and __ to form __. Ether is not necessary for this reaction. __ are made and used in a wide variety of solvents, including alkanes.
    • alkyl halides
    • vinyl halides
    • aryl halides
    • organometallic compounds
    • organolithium reagents
  10. Because they resemble carbanions, __ and __ are strong nucleoophiles nad strong bases. Their most useful necleophilic reactions are added to carbonyl groups. The carbonyl group is __, with a __ on carbon and a __ on oxygen. The positively charged carbon is __; attack by a __ places a negative charge on the electronegative oxygen atom.
    • Grignard
    • organolithium reagents
    • polarized
    • partial positive charge 
    • partial negative charge
    • electrophilic
    • nucleoophile
  11. The product of an __ is an __, a strong base. Addition of awter or a dilute acid in a second step __ the alkoxide to give the __.
    • nucleophilc attack
    • alkoxide ion
    • protonates
    • alcohol
  12. Either a __ or an __ can serve as the __ in the addition to a carbonyl group. 

    The __ first adds to the carbonyl group to form an alkoxide ion. Addition of __ (in a separate step) protonates the __ to give the __.
    • Grignard reagent
    • organolithium reagent
    • nucleophile
    • Grignard reagent
    • dilute acid
    • alkoxide 
    • alcohol
  13. __ has two hydrogen atoms bonded to the carbonyl group.

    __ and __ are strong nucleophiles that add to __ and __ to give alkoxide ions, which are protonated to give alcohols.
    formaldehyde

    • Grignard and organolithium reangents
    • ketones
    • aldehydes
  14. Mechanism of Grignard Reactions
    1) Formation of the Grignard reagent: Mg reacts with an alkyl haide in an anhydrous ehter solution

    • Reaction 1: The Grignard reagent attacks a carbonyl compound to form an alkoxide salt
    • Reaction 2: After the first rxn. is complete, water or dilute acid is added to protonate the alkoxide and give the alcohol
  15. Addition of a __ to __, followed by protonation, gives a __ with one more carbon atom than in the __

    __ add to __ to give, after protonation, __.
    • grignard reagent
    • formaldehyde
    • primary alcohol
    • GR

    • GR
    • aldehydes 
    • secondary alcohols
  16. The two alkyl groups of the secondary alcohol are the __ and hte __.

    Addition of a __, followed by protonation, to a __ gives a __, with three alkyl groups bonded to the __. Two of the alkyl groups are the __ . The third alkyl group comes from the __.
    • alkyl group form the GR
    • alkyl group that was bonded to the carbonyl group of hte aldehyde

    • GR
    • ketone
    • tertiary alcohol
    • carbinol carbon atom
    • two originally bonded to the ketone carbonyl group
    • GR
  17. __ and __ are derivatives of carboxylic acids. In such __, the -OH groups of a carboxylic acid is replaced by other __. In __, the hydroxyl group of the acid is replaced by a chlorine atom. In esters, the hydroxyl group is replaced by an __.
    • acid chlorides
    • esters
    • acid derivatives
    • electron-withdrawing groups
    • acid chlorides
    • alkoxyl group
  18. Acid chlorides and esters react with two equivalents of __ to give tertiary alcohols. Addition of the first equivalent of the __ produces an unstable intermediate that expels a __ or an __ to give a __. The __ is a suitable leaving group in this reaction because its leaving does what?
    • GR x2
    • chloride ion (in the acid chloride)
    • alkoxide ion (in the ester) 
    • ketone
    • alkoxide ion
    • stabilizes a negatively charged intermediate in a fast, strongly exothermic step
  19. The __ reacts with a second equivalent of the __, forming the Mg salt of a __. Protonation gives a __ with its alkyl groups derived from the __, and the other two derived from the __.
    • ketone
    • GR
    • tertiary alkoxide
    • tertiary alcohol
    • acid chloride or ester
    • GR
  20. Grignard reagents usually don't react with __, but __ are unusually reactive ethers because of the __. __ reacts with Grignard reagents to give, afte rprotonation, primary alcohols with two additional carbon atoms. The nucleophilc attack by the GR opens the ring and relieves the ring strain.
    • ethers
    • epoxides
    • ring strain
    • ethylene oxide

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