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A compound that contains an –OH (hydroxyl) group bonded to a tetrahedral carbon
Alcohol
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are alcohols, non-polar or polar
polar
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they are associated by hydrogen bonding in liquid state
alcohols
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alcohols have high or low boiling points?
high due to hydrogen bonding
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Boiling points also increase with increasing molecularweight (increased London dispersion forces)
-the higher the chair, the higher to bp
alcohol
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are more soluble in water than hydrocarbons ofsimilar molecular weight (due to H-bonding with water).
- the more non-polar the less soluble in water
alcohol
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1. No reaction with strong bases
2.Dehydration to form alkenes
3.Oxidation to aldehydes, ketones, and carboxylic acids
alcohol
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phenol DOES react with
a strong base (strong base NaOH)
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Elimination of a molecule of water from adjacent carbon atoms gives an alkene.
is most often brought about by heating
dehydration
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1o are the most difficult to dehydrate and require ___ temperatures
HIGH
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2o undergo acid-catalyzed dehydration at somewhat ___ temperatures than 1o
lower
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3o generally undergo acid-catalyzed dehydration at temperatures only slightly ____ above room temperature
above
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in dehydration of alcohols: the alkene with the product with the MOST alkyl groups is called
major product
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in dehydration of alcohols, the alkene product with the lower amount of alkyl groups is called the
minor product
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in dehydration-hydration of alcohols the reactant side has a + H2O makes the arrow favor what side
right -->
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in dehydration-hydration of alcohols the reactant side has a - H2O the arrow favors what side?
left <-----
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(loss of H or gain of O)
oxidation
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Oxidation of a 1o alcohol gives an
- aldehyde or a carboxylic acid
- 1st aldehyde then final product carboxylic acid
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oxidation of alcohol is commonly carried out using
K2Cr2O7
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oxidation of a 2o alcohol gives a
ketone
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Oxidation of tertiary alcohols are
reistant to oxidation N.R.
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It is sometimes possible to stop the oxidation at the aldehyde stage by
distilling
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oxygen atom bonded to two carbon atoms.
ethers
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use common names to name these molecules
ethers
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An ether in which one of the atoms in a ring is oxygen.
Cyclic ethers
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polar compounds, but weak dipole-dipole bodning
ethers
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low boiling points and low molecular weight
ethers
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they do not react with oxidation agents
they do not react with reducing agents
they are not affected by most acids or bases
ethers
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inertness
stable, and unreactive. helps disolve things but does not react (like a catalyst)
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a compound containing an sulfhydrhyl group (SH)
thiols
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these are stinky,
have low molecular weights.
nonpolar covalent.
no hydrogen bonding
low bp.
less soluble in water than alcohols
thiols
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mercaptan
means you have a thiol
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these react with strong bases such as NaOH to from water-soluble salts
thiols
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NaOH base H2O> salt + water
Thiol reacts with strong base always have a salt and water as product
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Thiols are readily oxidized to disulfides (s-s) by
O2
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Oxidation of thiols
you take the H off and combine the a diplicate molecule by attaching the Ss together
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Nonsuperposable mirror images
they are different molecules
enantiomers
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one object either the original object or the mirror object.
ex: hand
chiral
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a carbon with four different groups bonded to it
stereocenter
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an object that its mirror image is superposable, then they are identical and called
achiral
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a mixture of equal amounts of two enantiomers
racemic mixture
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always comes in pairs
enantiomers
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to assign a name to enantiomers
step 1: is it stereocenter?
step 2: assign priority of atoms directly attacted to stereocenter ( if same then go to next atom of that molecule) look @ P.table the higher atomic number the higher the priority
step 3: the lowest priority (4) has to face back
step 4: draw arrows from 1,2,3
step 5: if arrows turn right then R if arrows turn left then S
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if the lowest priority of enantiomer to assign R or S is not facing back then just go through all steps and switch the S, or R at the end
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for a molecule with n stereocenters the maximum number of possible steroiomers is
- 2n
- ex: there are 2 stereocenters in molecule. so its 22 = 4
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stereoisomers that are not mirror images but attachments are the same
- diastereomers:
- so just take one chiral from an enantiomer and another chiral from a different enantiomer to get diastereomers
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light waves vibrating only in parallel planes
narrows light down
plane of polarized light
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showing that a compound is capable of rotating the plane of plan-polarized light
rotates light
- optically active
- use a polarimeter to change/roate light direction
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clockwise rotation of the plane of plane-polarized light indicated by +
dextrorotary
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counterclockwise rotation of the plane of plane-polarized light indicated by -
levorotatory
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