which one is limiting reagent??

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 62GP: The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a...
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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.
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)
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)
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