Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
Related questions
Question
which one is limiting reagent??
![OCEDURE
ہاں
Lab 3: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde
substance
4-methoxybenzaldehyde
1-(4-methoxyphenyl)-
2-methylpropan-1-ol*
●
phosphoric acid, 1M
sodium chloride,
saturated solution
Preview
sodium hydroxide, 5%
10 mL
* amount varies, depending on size of drying tube
product
quantity
0.68 g
15 mL
10 mL
Assemble the reflux apparatus
Flame-dry a round-bottom flask
molar mass
(g/mol)
136.15
180.21
CHEMICAL ALERT
• Weigh magnesium turnings
Add magnesium and iodine to the dried round-bottom flask
Heat the reflux apparatus to flood the apparatus with iodine vapor
• Weigh 2-bromopropane and dissolve it in anhydrous diethyl ether
Add 2-bromopropane solution to the magnesium turnings and reflux to
make the Grignard reagent
mp
(°C)
-1
• Weigh 4-methoxybenzaldehyde and dissolve it in anhydrous diethyl
ether
Add 4-methoxybenzaldehyde portions to the Grignard reagent
Heat 10 min with a hot-water bath
Pour the mixture into ice water and acidify it with phosphoric acid
custom page
38
• Dry the ether layer with anhydrous magnesium sulfate
Remove the ether from the product
• Weigh the product
Characterize the product using TLC, IR, and NMR
2-bromopropane-flammable and irritant
calcium chloride-irritant and hygroscopic
dichloromethane-toxic and irritant
diethyl ether-flammable and toxic
iodine-toxic and corrosive
magnesium-flammable
bp
(°C)
• Separate the layers
●
Extract the product into ether and wash it with 5% NaOH and saturated
NaCl solution
248
27.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe0440bae-aaea-4b30-a6d7-59f732dd66dd%2Fa3ba5a76-db09-4d64-bd81-39716b00c7eb%2F1ba3jg_processed.jpeg&w=3840&q=75)
Transcribed Image Text:OCEDURE
ہاں
Lab 3: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde
substance
4-methoxybenzaldehyde
1-(4-methoxyphenyl)-
2-methylpropan-1-ol*
●
phosphoric acid, 1M
sodium chloride,
saturated solution
Preview
sodium hydroxide, 5%
10 mL
* amount varies, depending on size of drying tube
product
quantity
0.68 g
15 mL
10 mL
Assemble the reflux apparatus
Flame-dry a round-bottom flask
molar mass
(g/mol)
136.15
180.21
CHEMICAL ALERT
• Weigh magnesium turnings
Add magnesium and iodine to the dried round-bottom flask
Heat the reflux apparatus to flood the apparatus with iodine vapor
• Weigh 2-bromopropane and dissolve it in anhydrous diethyl ether
Add 2-bromopropane solution to the magnesium turnings and reflux to
make the Grignard reagent
mp
(°C)
-1
• Weigh 4-methoxybenzaldehyde and dissolve it in anhydrous diethyl
ether
Add 4-methoxybenzaldehyde portions to the Grignard reagent
Heat 10 min with a hot-water bath
Pour the mixture into ice water and acidify it with phosphoric acid
custom page
38
• Dry the ether layer with anhydrous magnesium sulfate
Remove the ether from the product
• Weigh the product
Characterize the product using TLC, IR, and NMR
2-bromopropane-flammable and irritant
calcium chloride-irritant and hygroscopic
dichloromethane-toxic and irritant
diethyl ether-flammable and toxic
iodine-toxic and corrosive
magnesium-flammable
bp
(°C)
• Separate the layers
●
Extract the product into ether and wash it with 5% NaOH and saturated
NaCl solution
248
27.
![1998 Cengage Learning
H3C
Br
Lab 3: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde
CH3
2-bromopropane
Mg
ether
reagent with 4-methoxybenzaldehyde to form a secondary alcohol, 1-(4-
methoxyphenyl)-2-methylpropan-1-ol, as shown in Equation 5.
H3C
MgBr
CH3
isopropyl magnesium
bromide
+
Equipment
50-mL beaker
100-mL beaker
250-mL beaker*
boiling chip
Bunsen burner
capillary tubes
condenser, with tubing
cotton
distilling head
drying tube, with stopper
OCH3
4-methoxybenzaldehyde
substance
Reagents and Properties
H
2-bromopropane
calcium chloride, anhydrous
dichloromethane
diethyl ether, anhydrous
diethyl ether, solvent grade
iodine
magnesium
magnesium sulfate, anhydrous
custom page
37
H+
H₂O
2 Erlenmeyer flasks, 25-mL
2 Erlenmeyer flasks, 50-mL,
with stopper
250-mL Erlenmeyer flask
filter funnel
fluted filter paper
25-mL graduated cylinder
4-oz jar, with lids
*or concentric ring bath for hot-water bath
preparing micropipets
* for
For glass stirring rod
Sor 250-ml beaker with foil or plastic wrap as cover for TLC developing chamber
НО.
OCH3
1-(4-methoxyphenyl)-
2-methylpropan-1-ol
magnetic stir bar
magnetic stirrer
magnetic wand*
microspatula
quantity
1.48 g
8 g*
5 mL
20 mL
22 mL
0.02 g
0.36 g
2 g
paper towel
Pasteur pipet, with latex bulb
pencil
pH paper
1.0-mL pipet
product vial
2 round-bottom flasks, 50-mL
ruler
125-mL separatory funnel
3 x 7-cm silica gel TLC plate
2 support stands
2 utility clamps
2.0-mL vial, with cap
molar mass
(g/mol)
123.0
110.99
84.93
74.12
74.12
253.8
24.3
120.37
mp
(°C)
(Eq. 5)
113
bp
(°C)
59
40
34.6
34.6
184
(Continued)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe0440bae-aaea-4b30-a6d7-59f732dd66dd%2Fa3ba5a76-db09-4d64-bd81-39716b00c7eb%2Fidga48e_processed.jpeg&w=3840&q=75)
Transcribed Image Text:1998 Cengage Learning
H3C
Br
Lab 3: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde
CH3
2-bromopropane
Mg
ether
reagent with 4-methoxybenzaldehyde to form a secondary alcohol, 1-(4-
methoxyphenyl)-2-methylpropan-1-ol, as shown in Equation 5.
H3C
MgBr
CH3
isopropyl magnesium
bromide
+
Equipment
50-mL beaker
100-mL beaker
250-mL beaker*
boiling chip
Bunsen burner
capillary tubes
condenser, with tubing
cotton
distilling head
drying tube, with stopper
OCH3
4-methoxybenzaldehyde
substance
Reagents and Properties
H
2-bromopropane
calcium chloride, anhydrous
dichloromethane
diethyl ether, anhydrous
diethyl ether, solvent grade
iodine
magnesium
magnesium sulfate, anhydrous
custom page
37
H+
H₂O
2 Erlenmeyer flasks, 25-mL
2 Erlenmeyer flasks, 50-mL,
with stopper
250-mL Erlenmeyer flask
filter funnel
fluted filter paper
25-mL graduated cylinder
4-oz jar, with lids
*or concentric ring bath for hot-water bath
preparing micropipets
* for
For glass stirring rod
Sor 250-ml beaker with foil or plastic wrap as cover for TLC developing chamber
НО.
OCH3
1-(4-methoxyphenyl)-
2-methylpropan-1-ol
magnetic stir bar
magnetic stirrer
magnetic wand*
microspatula
quantity
1.48 g
8 g*
5 mL
20 mL
22 mL
0.02 g
0.36 g
2 g
paper towel
Pasteur pipet, with latex bulb
pencil
pH paper
1.0-mL pipet
product vial
2 round-bottom flasks, 50-mL
ruler
125-mL separatory funnel
3 x 7-cm silica gel TLC plate
2 support stands
2 utility clamps
2.0-mL vial, with cap
molar mass
(g/mol)
123.0
110.99
84.93
74.12
74.12
253.8
24.3
120.37
mp
(°C)
(Eq. 5)
113
bp
(°C)
59
40
34.6
34.6
184
(Continued)
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
Step 1
This is a two-step reaction.
Step-1:
2-bromopropane reacts with Mg to give the Grignard reagent, isopropyl magnesium bromide.
Step-2:
isopropyl magnesium bromide reacts with 4-methoxybenzaldehyde and H3O+ to give a secondary alcohol as the final product.
In both the cases, the mole ration is 1/1.
Hence the reactant with smaller mole is the limiting reactant.
Step by step
Solved in 3 steps
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