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1

in alcoholic beverages

used as a fuel

also called "grain alcohol"

toxicity: alcohol poisoning (decreased breathing, heart rate and gag reflex), long term use (bad for memory, liver and can cause addiction), and fetal alcohol syndrome in pregnant women

ethyl alcohol (ethanol)

2

cyclic ethers

the O of an ether contained in a ring

these compounds make good solvents because they are unreactive

one type is "Crown ethers" - form complexes with cations. phase transfer catalysts

2

flammable

oxidize in air to form unstable peroxides which leads to explosion hazard

unreactive towards acids, bases and oxidizing agents

can be halogenated

chemical properties of ethers

3

glycol = a diol in which 2 –OH groups are on adjacent Carbons
antifreeze & de-icers (depresses freezing and lowers freezing point)
Toxicity:  etylene glycol is metabolized to oxalic acid (Forms calcium salt crystals in the kidneys which leads to renal failure)

ethylene Glycol (1,2-ethanediol) &

propylene Glycol (1,2-propanediol)

3

removal of H20 components that results in an alkene and water

can result in 2 different alkenes (major and minor determined by Zaitsev's rule)

this changes a single bond to a double bond (reverse of addition reaction)

only 2° and 3° alcohols can undergo this

requires an acid (H2SO4) and heat

dehydration / elimination reaction

3

rule that determines major and minor products in a dehydration reaction

most highly substituted alkene will predominate (alkene with most alkyl groups)

Zaitsev's rule

5

methyl alcohol (methanol)

the simplest alcohol

used to be used as fuel in race cars

used as a solvent for shellacs and varnishes

also called "wood alcohol"

toxic: can cause blindness and decrease pH pf blood

5

the O of an ether contained in a ring

these compounds make good solvents because they are unreactive

one type is "Crown ethers" - form complexes with cations. phase transfer catalysts

cyclic ethers

5

Low boiling point compared to alcohol – cannot form H-bonds
Disagreeable odor - methanethiol is added to natural gas to make leaks detectable
Oxidation Reactions – the product is a disulfide
Weak Acids – more acidic than phenols
 

properties of thiols

6

small alcohol (1-3 C) are soluble in water

4 C is partially soluble

5+ is completely insoluble

solubility of alcohol

7

KMnO4 

  K2Cr2O7  

  H2CrO4

oxidizing agents

8

isopropyl alcohol (2-propanol)

rubbing alcohol
used to cool the skin (decrease fever)
Toxicity: more toxic than ethanol, but causes fewer fatalities becaus bitter taste, causes vomiting

8

rubbing alcohol
used to cool the skin (decrease fever)
Toxicity: more toxic than ethanol, but causes fewer fatalities becaus bitter taste, causes vomiting

isopropyl alcohol (2-propanol)

9

organic compound where a sulfur atom is bonded to 2 carbon atoms by single bonds

Analogs of ethers
characteristic odors:  garlic, onions

thioether

10

organic compound where a sulfhydryl group is bonded to a saturated C atom

sulfur analogs of alcohols

contain SH functional groups instead of OH

thiols

11

ethyl alcohol (ethanol)

in alcoholic beverages

used as a fuel

also called "grain alcohol"

toxicity: alcohol poisoning (decreased breathing, heart rate and gag reflex), long term use (bad for memory, liver and can cause addiction), and fetal alcohol syndrome in pregnant women

12

reaction with alcohol and HBr/HCl

nucleophile attacks carbon with the OH group (Br is better nucleophile than Cl)

Water is forced out

e.g. Lucas test reacts with 3° and 2° but not 1°

substitution

12

flammable (combustion reactions)

can't be dehydrated

doesn't react with mild oxidizing agents

substitution of OH with a halogen

weak acids

chemical properties of phenols

13

dehydration / elimination reaction

removal of H20 components that results in an alkene and water

can result in 2 different alkenes (major and minor determined by Zaitsev's rule)

this changes a single bond to a double bond (reverse of addition reaction)

only 2° and 3° alcohols can undergo this

requires an acid (H2SO4) and heat

14

Zaitsev's rule

rule that determines major and minor products in a dehydration reaction

most highly substituted alkene will predominate (alkene with most alkyl groups)

14

thiols

organic compound where a sulfhydryl group is bonded to a saturated C atom

sulfur analogs of alcohols

contain SH functional groups instead of OH

15

the simplest alcohol

used to be used as fuel in race cars

used as a solvent for shellacs and varnishes

also called "wood alcohol"

toxic: can cause blindness and decrease pH pf blood

methyl alcohol (methanol)

16

chemical properties of ethers

flammable

oxidize in air to form unstable peroxides which leads to explosion hazard

unreactive towards acids, bases and oxidizing agents

can be halogenated

17

a carbon atom that gains oxygen or loses hydrogen is oxidized

a carbon atom that loses oxygen or gains hydrogen is reduced

primary and secondary undergo this reaction, tertiary do not (because they do not have H attached to OH-bearing C

primary produce aldehyde and then carboxylic acid

secondary produce ketone

oxidation reaction

19

chemical properties of phenols

flammable (combustion reactions)

can't be dehydrated

doesn't react with mild oxidizing agents

substitution of OH with a halogen

weak acids

20

Glycerol (1, 2,3-propanetriol)

lubricant
used in lotions, soaps, shaving cream, etc.
“biological antifreeze” - some insects have this in blood to decrease freezing point
a normal product of fat metabolism - triglycerides
 

22

thioether

organic compound where a sulfur atom is bonded to 2 carbon atoms by single bonds

Analogs of ethers
characteristic odors:  garlic, onions

23

low melting solids or oily liquids at room temp

most are not very soluble in water

colorless, volitile solid

mildly acidic and can cause bad chemical burns

vapors of these are bad for eyes / respiratory tract

used as antimicrobial/antiseptic to kill germs

physical properties of phenols

25

condensation

removal of H2O (water is liberated)

2 molecules combine to form a larger one

only 1° alcohols undergo this

product is an ether

26

common alcohols are liquid at room temp

boiling point increases as the length of carbon chain increases (due to increased intermolecular forces that require more heat to pull them apart)

alcohols with more than one OH group have significantly higher boiling points

boiling point of alcohol