Chapter 14

Question 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

Answer 1

ethyl alcohol (ethanol)

Question 2

cyclic ethers

Answer 2

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

Question 2

flammable

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

unreactive towards acids, bases and oxidizing agents

can be halogenated

Answer 2

chemical properties of ethers

Question 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)

Answer 3

ethylene Glycol (1,2-ethanediol) &

propylene Glycol (1,2-propanediol)

Question 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

Answer 3

dehydration / elimination reaction

Question 3

rule that determines major and minor products in a dehydration reaction

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

Answer 3

Zaitsev’s rule

Question 5

methyl alcohol (methanol)

Answer 5

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

Question 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

Answer 5

cyclic ethers

Question 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

Answer 5

properties of thiols

Question 6

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

4 C is partially soluble

5+ is completely insoluble

Answer 6

solubility of alcohol

Question 7

KMnO4

K2Cr2O7

H2CrO4

Answer 7

oxidizing agents

Question 8

isopropyl alcohol (2-propanol)

Answer 8

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

Question 8

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

Answer 8

isopropyl alcohol (2-propanol)

Question 9

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

Analogs of ethers
characteristic odors: garlic, onions

Answer 9

thioether

Question 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

Answer 10

thiols

Question 11

ethyl alcohol (ethanol)

Answer 11

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

Question 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°

Answer 12

substitution

Question 12

flammable (combustion reactions)

can’t be dehydrated

doesn’t react with mild oxidizing agents

substitution of OH with a halogen

weak acids

Answer 12

chemical properties of phenols

Question 13

dehydration / elimination reaction

Answer 13

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

Question 14

Zaitsev’s rule

Answer 14

rule that determines major and minor products in a dehydration reaction

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

Question 14

thiols

Answer 14

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

sulfur analogs of alcohols

contain SH functional groups instead of OH

Question 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

Answer 15

methyl alcohol (methanol)

Question 16

chemical properties of ethers

Answer 16

flammable

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

unreactive towards acids, bases and oxidizing agents

can be halogenated

Question 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

Answer 17

oxidation reaction

Question 19

chemical properties of phenols

Answer 19

flammable (combustion reactions) can't be dehydrated doesn't react with mild oxidizing agents substitution of OH with a halogen weak acids

Question 20

Glycerol (1, 2,3-propanetriol)

Answer 20

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

Question 22

thioether

Answer 22

organic compound where a sulfur atom is bonded to 2 carbon atoms by single bonds Analogs of ethers characteristic odors: garlic, onions

Question 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

Answer 23

physical properties of phenols

Question 25

condensation

Answer 25

removal of H2O (water is liberated) 2 molecules combine to form a larger one only 1° alcohols undergo this product is an ether

Question 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

Answer 26

boiling point of alcohol

Question 27

boiling point similar to alkanes but much lower than alcohol. because these cannot hydrogen bond with each other so they are easier to break apart solubility similar to alcohols because these can hydrogen bond with water due to its O

Answer 27

physical properties of ethers

Question 28

ethers

Answer 28

organic compound where an oxygen atom is bonded to 2 carbon atoms by single bonds used as general surgery anesthetic - today they are halogenated because it is less flammable

Question 30

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

Answer 30

Glycerol (1, 2,3-propanetriol)

Question 31

alcohol

Answer 31

hydrocarbon derivative with a single O atom. organic compound in which an -OH group is bonded to a saturated carbon atom (carbon atom that is bonded to 4 other atoms) generalized formula is R-OH

Question 32

oxidizing agents

Answer 32

KMnO4 K2Cr2O7 H2CrO4

Question 33

physical properties of phenols

Answer 33

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

Question 35

ethylene Glycol (1,2-ethanediol) & propylene Glycol (1,2-propanediol)

Answer 35

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)

Question 36

removal of H2O (water is liberated) 2 molecules combine to form a larger one only 1° alcohols undergo this product is an ether

Answer 36

condensation

Question 38

oxidation reaction

Answer 38

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

Question 39

hydrocarbon derivative with a single O atom. organic compound in which an -OH group is bonded to a saturated carbon atom (carbon atom that is bonded to 4 other atoms) generalized formula is R-OH

Answer 39

alcohol

Question 40

organic compound where an OH is bonded to a C that is part of an aromatic ring uses: antiseptics, antioxidants (prevents other substances from oxidizing, prevetns food from spoiling), flavoring agent (cloves and vanillin), and pharmaceutical agents (general anesthesia)

Answer 40

phenol

Question 42

solubility of alcohol

Answer 42

small alcohol (1-3 C) are soluble in water 4 C is partially soluble 5+ is completely insoluble

Question 43

phenol

Answer 43

organic compound where an OH is bonded to a C that is part of an aromatic ring uses: antiseptics, antioxidants (prevents other substances from oxidizing, prevetns food from spoiling), flavoring agent (cloves and vanillin), and pharmaceutical agents (general anesthesia)

Question 44

physical properties of ethers

Answer 44

boiling point similar to alkanes but much lower than alcohol. because these cannot hydrogen bond with each other so they are easier to break apart solubility similar to alcohols because these can hydrogen bond with water due to its O

Question 45

organic compound where an oxygen atom is bonded to 2 carbon atoms by single bonds used as general surgery anesthetic - today they are halogenated because it is less flammable

Answer 45

ethers

Question 46

substitution

Answer 46

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°

Question 47

properties of thiols

Answer 47

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

Question 48

boiling point of alcohol

Answer 48

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