age 1 of 65
CHEM 219 Module 3 Problem Set Principles of Organic
Chemistry with Lab FINAL EXAM STUDY GUIDE
2025/2026 COMPLETE QUESTIONS WITH CORRECT
DETAILED ANSWERS || 100% GUARANTEED PASS
<BRAND NEW VERSION>
to promote formation of the alkoxide ion .....Answer.....alcohol
can be treated with sodium or potassium metal (Na or K) or a
base that is stronger than the RO- ion produced
dehydration of alcohols .....Answer.....when heated with strong
mineral acids like sulfuric or phosphoric, refers to loss of water
alcohol loses H20 and forms an alkene
,age 2 of 65
*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 .....Answer.....ethene
function of acid in dehydration of an alcohol
.....Answer.....protonate the OH group of the alcohol
first step of dehydration of alcohol .....Answer.....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
.....Answer.....E1 - the OH group is protonated and then
dissociates forming a carbocation
,age 3 of 65
typically water (acting as a base) removes a beta-hydrogen to
form the alkene
non-bulky (primary) alcohols dehydrate by __ .....Answer.....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) .....Answer.....tertiary
(least harsh conditions) > secondary > primary (harsh conditions)
when more than one beta-carbon on alcohol, dehydration can
produce .....Answer.....more than one alkene product (major and
minor)
Zaitsev's rule .....Answer.....major product is the more highly
substituted alkene (which is the alkene whose C=C has more
alkyl groups attached)
, age 4 of 65
Conversion of alcohol to alkyl halide using hydrogen halides
.....Answer.....alcohol + hydrogen-halide -----> alkyl halide +
water
R-OH + H-X ----> R-X + H-OH
*substitution over elimination since halide ions are good
nucleophiles but weak bases
*acid protonates hydroxyl group of alcohol, making it a good
leaving group
order of reactivity of alcohols with hydrogen halides
.....Answer.....same as dehydration; tertiary easiest > secondary
> primary hardest
Tertiary alcohols react via ____ to become an alkyl halide
.....Answer.....Sn1 mechanism
CHEM 219 Module 3 Problem Set Principles of Organic
Chemistry with Lab FINAL EXAM STUDY GUIDE
2025/2026 COMPLETE QUESTIONS WITH CORRECT
DETAILED ANSWERS || 100% GUARANTEED PASS
<BRAND NEW VERSION>
to promote formation of the alkoxide ion .....Answer.....alcohol
can be treated with sodium or potassium metal (Na or K) or a
base that is stronger than the RO- ion produced
dehydration of alcohols .....Answer.....when heated with strong
mineral acids like sulfuric or phosphoric, refers to loss of water
alcohol loses H20 and forms an alkene
,age 2 of 65
*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 .....Answer.....ethene
function of acid in dehydration of an alcohol
.....Answer.....protonate the OH group of the alcohol
first step of dehydration of alcohol .....Answer.....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
.....Answer.....E1 - the OH group is protonated and then
dissociates forming a carbocation
,age 3 of 65
typically water (acting as a base) removes a beta-hydrogen to
form the alkene
non-bulky (primary) alcohols dehydrate by __ .....Answer.....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) .....Answer.....tertiary
(least harsh conditions) > secondary > primary (harsh conditions)
when more than one beta-carbon on alcohol, dehydration can
produce .....Answer.....more than one alkene product (major and
minor)
Zaitsev's rule .....Answer.....major product is the more highly
substituted alkene (which is the alkene whose C=C has more
alkyl groups attached)
, age 4 of 65
Conversion of alcohol to alkyl halide using hydrogen halides
.....Answer.....alcohol + hydrogen-halide -----> alkyl halide +
water
R-OH + H-X ----> R-X + H-OH
*substitution over elimination since halide ions are good
nucleophiles but weak bases
*acid protonates hydroxyl group of alcohol, making it a good
leaving group
order of reactivity of alcohols with hydrogen halides
.....Answer.....same as dehydration; tertiary easiest > secondary
> primary hardest
Tertiary alcohols react via ____ to become an alkyl halide
.....Answer.....Sn1 mechanism
