Orgo Ch 10 Notes

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DesLee26
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255533
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Orgo Ch 10 Notes
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2014-01-09 19:15:07
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CHM 202
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  1. Structure of water and methanol
    - Oxygen is __ and __.
    - The H-O-H angle in water is __.
    - The C-O-H angle in methyl alcohol is __.
    • sp3 hybridized
    • tetrahedral
    • 104.5
    • 108.9
  2. __ is the most abundant of opium's alkaloids. 

    __ is a central nervous system depressant as it depresses brain areas responsible for __. 

    Ethanol oxidizes to __, then __, which is a normal metabolite.
    morphine

    ethanol; judgment

    acetaldehyde; acetic acid
  3. Excess __ can cause metabolic problems. 
    __ is normally converted to __. Results in __ and __.

    In men, what does ethanol do and why?
    • NADH
    • pyruvic acid
    • glucose (gluconeogenesis)
    • acidosis
    • hypoglycemia

    lowers levels of testosterone (and sperm count) due to lack of enzymes needed for steroid biosynthesis
  4. The enzyme __, which is responsible converting __ into liver toxins, is activated by __. 

    __ has a caloric value of __. 

    Alcohol can cause a __ called __ (3x more common than __).
    • CYP2E1
    • acetaminophen
    • ethanol
    • ethanol
    • 7.1 Cal/g
    • degenerative muscle disease
    • alcoholic myopathy
    • cirrhosis
  5. Women will have higher __ with the consumption of an equal number of drinks due to lower __ activity and lower __ in blood. 

    __ levels increase in women (and men). THis has been associated with higher incidences of __ and a change in __.

    A higher than normal concentration of __ (in the liver) are activated by __ creating a potential __.
    • BAL's
    • percent H2O
    • estradiol
    • heart disease
    • bone density
    • cytochrome P-450 enzymes
    • ethanol
    • dependency
  6. Antitumor Agents

    Often functionalized with __

    Designed to fit into specific __ on __.

    __ is crucial for binding

    __ is crucial for cell membrane transport
    • alcohols
    • geometic sites on proteins
    • Hydrogen bonding
    • Water solubility
  7. How Taxol Works 

    A large number of microtubules are formed at the start of __, and as __ comes to an end, these microtubules are normally broken down into __– a protein responsible for the cell’s structural stability.

    Taxol promotes __ then binds to the microtubules and inhibits their __back into tubulin.

    The cell can't divide into __ and therefore the cancer can’t spread.
    • cell division
    • cell division
    • tubulin 

    • tubulin polymerization
    • depolymerization

    daughter cells
  8. __ inhibits tubulin aggression

    __ binds to DNA and inhibits the enzyme topoisomerase II.
    • epothilone B
    • doxorubicin (adriamycin)
  9. IUPAC Nomenclature
    • 1) Find the longest carbon chain containing the carbon with the —OH group.
    • 2) Drop the -e from the alkane name; add -ol.
    • 3) Number the chain, giving the —OH group the lowest number possible.
    • 4) Number and name all substituents and write them in alphabetical order.
  10. Boiling Points of Alcohols

    Alcohols have __ than ethers and alkanes because alcohols __.

    The stronger interaction between __ molecules will require __, resulting in a __ BP.
    • higher BPs
    • can form hydrogen bonds
    • alcohol molecules
    • more energy to break
    • higher
  11. Acidity of Alcohols

    Due to the __ of the O atoms, alcohols are slightly __. 
    The __ derived by the __ of an alcohol is the __. 
    Alcohols also react with Na (or K) as water does to give the __ (__):
    • electronegativity
    • acidic
    • anion
    • deprotonation
    • alkoxide
    • alkoxide
    • (red-ox)
  12. Formation of Alkoxide Ions

    - __ reacts with sodium metal to form __, a strong base commonly used for __ reactions.
    - More hindered alcohols like __ or __ react faster with potassium than with sodium.
    • ethanol
    • sodium ethoxide
    • elimination
    • 2-propanol
    • tert-butanol
  13. What enhances acidity?

    Formation of Phenoxide Ion
    The __ is more __ than __ due to the ability of __ to delocalize the negative charge of the oxygen within the carbons of the ring.
    withdrawing groups

    • aromatic alcohol phenol
    • acidic
    • aliphatic alcohols
    • aromatic rings
  14. Charge delocalization on the phenoxide ion


    The __ of the oxygen can be delocalized over __ of the __.
    The true structure is a __ between the four __.
    • negative charge
    • four atoms
    • phenoxide ion
    • hybrid
    • resonance forms
  15. What are six ways of preparing alcohols?
    • 1) reduction of ketones and aldehydes
    • 2) reduction of esters and carboxylic acids
    • 3) hydration of alkenes
    • 4) nucleophilic addition
    • ---- Grignard reaction
    • ---- Acetylide addition
    • 5) Substitution
    • 6) Epoxide opening
  16. Oxymercuration Hydration is __ orientation. 

    What are the conditions?
    Mark

    • 1) Hg(OAc)2 in THF/H2O
    • 2) NaBH4
  17. Hydroboration hydration is __ orientation.

    What are the conditions?
    Anti-Mark

    • 1) BH3-THF
    • 2) H2O2, NaOH
  18. Oxidation and Reduction
    - how many hydrocarbon oxidation levels?
    - what is the chain?

    oxidation # of carbon in bold
    3

    CH3-CH3 --[O]--> CH2=CH2--[O]--> HC***HC

    -3                             -2                    -1
  19. Grignard Reagents
    1) Formula
    2) __ are used as __ to stabilize the complex.
    3) __ are most reactives. __ generally do not react.
    4) May be formed from __, __, or __.
    • 1) R-Mg-X (reacts like R:- +MgX)
    • 2) ethers/ solvents
    • 3) iodides/ fluorides
    • 4) primary, secondary, tertiary alkyl halides
  20. Grignard Reaction:

    ___ ---> ____
    CH3--Br  + Mg ------> CH3--MgBr (Grignard Reagent)

    • CH3- +MgBr  
    • excellent nucleophile (very strong base)
  21. Formation of Grignard Reagents occurs in __. 

    Grignard Reagents react with __ to form __.

    Grignard Reagents React With __ to form __.

    Grignard Reagents react with __ to form __.

    Grignard Reagents open __.
    ether

    aldehydes/ secondary alcohols

    ketones/ tertiary alcohols

    formaldehyde/ primary alcohols

    epoxides
  22. Grignard Reagents react __ with __ to form __.

    Conditions of reaction of Grignards with Carboxylic acid derivatives

    Grignard Reagents are __.

    What is an effective use of the basicity?
    • twice/ esters/ tertiary alcohols
    • 1) ether solvent
    • 2) H3O+

    exceptionally strong bases

    isotopic labeling
  23. NaBH4 reduction conditions?

    LiAlH4 reduction is __. What will it reduce?
    • 1) NaBH4, ethanol
    • 2) H3O+

    • a stronger reducing agent
    • ketones to secondary alcohols
    • aldehydes to primary alcohols
    • carboxylic acids and esters to primary alcohols
  24. __ is the stronger base, but __ is more selective.
    • LiAlH4
    • NaBH4
  25. •NaBH4 can reduce __ and __ but not __ and __.

    LiAlH4 is a __ and will reduce all __.
    • aldehydes and ketones
    • esters and carboxylic acids.
    • stronger reducing agent
    • carbonyls

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