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??

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.

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

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

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning

Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY