CHEM 219 - Module 5 Exam Questions Answered Correctly Latest Update 2025-2026
alcohols - Answers Generic formula R-OH
Defined by presence of hydroxyl group, derivatives of water (one H atoms is replaced by an alkyl
group (carbon-based group))
Phenols - Answers hydroxyl group connected to benzene ring
Nomenclature alcohols - Answers replace suffix of parent chain with -ol
*Hydroxyl group will have lowest possible number
Unsaturated alcohol nomenclature - Answers 2 endings needed: one for the C=C or C triple bond
C and one for the alcohol functional group; -ol suffix
Put number on the lowest part of the double or triple bond
(ex: 2-propen-1-ol)
polyols - Answers Molecules with more than one -OH group
*prefix describing number of -OH added to IUPAC name
(ex: ethane-1,2-diol)
diol, triol, etc
phenol - Answers refers to a specific molecule (hydroxybenzene) and to the parent name of all
hydroxy-substituted aromatic molecules (-OH attached to benzene ring)
primary vs secondary vs tertiary alcohols - Answers how many carbon atoms (alkyl groups)
directly attached to the carbon bearing the -OH group
methyl alcohol - Answers only hydrogen connected to carbon bearing the -OH group
Alcohol properties - Answers strong hydrogen bonding interactions with one another because of
presence of hydroxyl group (the O-H bond is highly polarized by the electronegative oxygen)
-->causes alcohols to have higher boiling points than other molecules of similar molecular
weight
-freely hydrogen bond to other molecules possessing O-H, N-H, or S-H
-lower MW alcohols are soluble in water
alcohol acidity and basicity - Answers can act as weak acids (donating O-H proton as H+) or as
weak bases (accepting H+ using a long pair on the O atom) depending on the environment
surrounding them aka AMPHOTERIC substances
, Acid dissociation of alcohols - Answers unfavorable (lies towards left) as dissociation produces
an alkoxide ion (conjugate base of an alcohol), which is a very strong base
typically, acid-base rxn formation of weaker conjugate acids/bases
to promote formation of the alkoxide ion - Answers alcohol can be treated with sodium or
potassium metal (Na or K) or a base that is stronger than the RO- ion produced
product of the protonation of an alcohol is known as an
*using lone pair on oxygen atom of hydroxyl group, alcohols can accept a proton when they are
placed in an acidic environment - Answers alkyloxonium ion
dehydration of alcohols - Answers when heated with strong mineral acids like sulfuric or
phosphoric, refers to loss of water
alcohol loses H20 and forms an alkene
*specific type of elimination rxn as alcohol substrate losing the hydroxyl (OH) from one carbon
(the alpha-carbon) and a hydrogen atom from the adjacent beta carbon
*opposite of hydration of alkenes
ethanol (ethyl alcohol) can be dehydrated to - Answers ethene
function of acid in dehydration of an alcohol - Answers protonate the OH group of the alcohol
first step of dehydration of alcohol - Answers alcohol acts as base and protonation of the
hydroxyl group making it a better leaving group, leaves neutral molecule of water
steric bulky (tertiary) alcohols dehydrate by __ mechanism - Answers E1 - the OH group is
protonated and then dissociates forming a carbocation
typically water (acting as a base) removes a beta-hydrogen to form the alkene
non-bulky (primary) alcohols dehydrate by __ - Answers E2 because these substrates do not
form stable carbocation intermediates; protonation of hydroxyl group is eliminated in a single
step by removal of beta-hydrogen
Ease of dehydration (easiest to hardest) - Answers tertiary (least harsh conditions) > secondary
> primary (harsh conditions)
when more than one beta-carbon on alcohol, dehydration can produce - Answers more than one
alkene product (major and minor)
Zaitsev's rule - Answers major product is the more highly substituted alkene (which is the alkene
alcohols - Answers Generic formula R-OH
Defined by presence of hydroxyl group, derivatives of water (one H atoms is replaced by an alkyl
group (carbon-based group))
Phenols - Answers hydroxyl group connected to benzene ring
Nomenclature alcohols - Answers replace suffix of parent chain with -ol
*Hydroxyl group will have lowest possible number
Unsaturated alcohol nomenclature - Answers 2 endings needed: one for the C=C or C triple bond
C and one for the alcohol functional group; -ol suffix
Put number on the lowest part of the double or triple bond
(ex: 2-propen-1-ol)
polyols - Answers Molecules with more than one -OH group
*prefix describing number of -OH added to IUPAC name
(ex: ethane-1,2-diol)
diol, triol, etc
phenol - Answers refers to a specific molecule (hydroxybenzene) and to the parent name of all
hydroxy-substituted aromatic molecules (-OH attached to benzene ring)
primary vs secondary vs tertiary alcohols - Answers how many carbon atoms (alkyl groups)
directly attached to the carbon bearing the -OH group
methyl alcohol - Answers only hydrogen connected to carbon bearing the -OH group
Alcohol properties - Answers strong hydrogen bonding interactions with one another because of
presence of hydroxyl group (the O-H bond is highly polarized by the electronegative oxygen)
-->causes alcohols to have higher boiling points than other molecules of similar molecular
weight
-freely hydrogen bond to other molecules possessing O-H, N-H, or S-H
-lower MW alcohols are soluble in water
alcohol acidity and basicity - Answers can act as weak acids (donating O-H proton as H+) or as
weak bases (accepting H+ using a long pair on the O atom) depending on the environment
surrounding them aka AMPHOTERIC substances
, Acid dissociation of alcohols - Answers unfavorable (lies towards left) as dissociation produces
an alkoxide ion (conjugate base of an alcohol), which is a very strong base
typically, acid-base rxn formation of weaker conjugate acids/bases
to promote formation of the alkoxide ion - Answers alcohol can be treated with sodium or
potassium metal (Na or K) or a base that is stronger than the RO- ion produced
product of the protonation of an alcohol is known as an
*using lone pair on oxygen atom of hydroxyl group, alcohols can accept a proton when they are
placed in an acidic environment - Answers alkyloxonium ion
dehydration of alcohols - Answers when heated with strong mineral acids like sulfuric or
phosphoric, refers to loss of water
alcohol loses H20 and forms an alkene
*specific type of elimination rxn as alcohol substrate losing the hydroxyl (OH) from one carbon
(the alpha-carbon) and a hydrogen atom from the adjacent beta carbon
*opposite of hydration of alkenes
ethanol (ethyl alcohol) can be dehydrated to - Answers ethene
function of acid in dehydration of an alcohol - Answers protonate the OH group of the alcohol
first step of dehydration of alcohol - Answers alcohol acts as base and protonation of the
hydroxyl group making it a better leaving group, leaves neutral molecule of water
steric bulky (tertiary) alcohols dehydrate by __ mechanism - Answers E1 - the OH group is
protonated and then dissociates forming a carbocation
typically water (acting as a base) removes a beta-hydrogen to form the alkene
non-bulky (primary) alcohols dehydrate by __ - Answers E2 because these substrates do not
form stable carbocation intermediates; protonation of hydroxyl group is eliminated in a single
step by removal of beta-hydrogen
Ease of dehydration (easiest to hardest) - Answers tertiary (least harsh conditions) > secondary
> primary (harsh conditions)
when more than one beta-carbon on alcohol, dehydration can produce - Answers more than one
alkene product (major and minor)
Zaitsev's rule - Answers major product is the more highly substituted alkene (which is the alkene
