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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
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__ 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
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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
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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
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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
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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
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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
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__ inhibits tubulin aggression
__ binds to DNA and inhibits the enzyme topoisomerase II.
- epothilone B
- doxorubicin (adriamycin)
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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.
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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
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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)
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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
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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
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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
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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
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Oxymercuration Hydration is __ orientation.
What are the conditions?
Mark
- 1) Hg(OAc)2 in THF/H2O
- 2) NaBH4
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Hydroboration hydration is __ orientation.
What are the conditions?
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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
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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
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Grignard Reaction:
___ ---> ____
CH3--Br + Mg ------> CH3--MgBr (Grignard Reagent)
- CH3- +MgBr
- excellent nucleophile (very strong base)
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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
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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
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NaBH4 reduction conditions?
LiAlH4 reduction is __. What will it reduce?
- a stronger reducing agent
- ketones to secondary alcohols
- aldehydes to primary alcohols
- carboxylic acids and esters to primary alcohols
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__ is the stronger base, but __ is more selective.
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•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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