ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Question
Chapter 15.12, Problem 17P
Interpretation Introduction
Interpretation:
The compound that would be hydrogenated to prepare naproxen, is to be identified.
Concept Introduction:
Hydrogenation is addition of hydrogen across vicinal atoms.
For hydrogenation to take place, the bonds between the vicinal atoms must be unsaturated.
Ru-BINAP is used as a hydrogenation catalyst.
When chiral ligands are used, new chirality centers with a particular configuration can be produced.
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Solution
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Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag
the appropriate image to the correct position in the reactions.)
Route 1
Aldehyde 1
or
+98
Aldehyde 2
Route 2
Q6
+100
Solved in 1 attempt
Q7
+95
Solved in 2 attempts
Q8
+98
Unlimited attempts
possible
+
+
Grignard 1
OH
H3O+
Grignard 2
Answer Bank
Q9
+90
MgBr
Unlimited attempts
possible
CH3CH2CH2MgBr
Q10
Unlimited attempts
Q11
?
?
+100
in 1 attempt
2-methyl-3-hexanol
CH3CH2MgBr
H
H
о
H
Attempt 3
2) (4 pt) After the reaction was completed, the student collected the following data. Crude
product data is the data collected after the reaction is finished, but before the product
is purified. "Pure" product data is the data collected after attempted purification using
recrystallization.
Student B's data:
Crude product data
"Pure"
product data
after
recrystallization
Crude mass: 0.93 g grey solid
Crude mp: 96-106 °C
Crude % yield:
Pure mass: 0.39 g white solid
Pure mp: 111-113 °C
Pure % yield:
a) Calculate the crude and pure percent yields for the student's reaction.
b) Summarize what is indicated by the crude and pure melting points.
Don't used hand raiting
Chapter 15 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 15.1 - Each of the following organometallic reagents will...Ch. 15.3 - Write equations showing how you could prepare...Ch. 15.4 - Lithium diisopropylamide is often used as a strong...Ch. 15.5 - Write the structure of the organic product of each...Ch. 15.7 - Prob. 5PCh. 15.8 - Prob. 6PCh. 15.9 - Prob. 7PCh. 15.9 - Like nickel, iron reacts with carbon monoxide to...Ch. 15.9 - Prob. 9PCh. 15.9 - What is the oxidation state of manganese in the...
Ch. 15.9 - Prob. 11PCh. 15.10 - Prob. 12PCh. 15.10 - Prob. 13PCh. 15.11 - Give the structure including stereochemistry of...Ch. 15.11 - Prob. 15PCh. 15.12 - Homogeneous catalytic hydrogenation of the...Ch. 15.12 - Prob. 17PCh. 15.13 - What alkenes are formed from 2-pentene by olefin...Ch. 15.13 - The product of the following reaction was isolated...Ch. 15 - Suggest appropriate methods for preparing each of...Ch. 15 - Prob. 21PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 23PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 25PCh. 15 - A different stereoisomer of...Ch. 15 - Prob. 27PCh. 15 - Using phenyllithium and any necessary organic or...Ch. 15 - Prob. 29PCh. 15 - A number of drugs are prepared by reactions in...Ch. 15 - The following conversion was carried out in two...Ch. 15 - Outline syntheses of (a)...Ch. 15 - (S)-(+)-Ibuprofen can be prepared by...Ch. 15 - Like other hydroborations, the reaction of alkynes...Ch. 15 - The sex attractant of the female silkworm has been...Ch. 15 - Prob. 36PCh. 15 - (a) Exaltolide, a musk substance, has been...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and (Cyclobutadiene)tricarbonyliron...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...
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