Williamson Ether Synthesis (continued on the next page): (1) ( ©) One of the following compounds shows exactly 1 signal in its 13C NMR spectrum, another one shows 2, one shows 3, one 4, one 5, and another one shows 6 signals. Draw them in the correct ascending order; i.e., have the one with 1 signal on the left side, then the one with 2 signals, then 3, then 4, then 5, and finally, the one with 6 signals. tos रे et रे (2) (3) a) Draw the ionic product if we had used isobutyl acohol for the first reaction with sodium metal. Include all valence electrons and charges. b) What would be the byproduct of this reaction? (5) What is the theoretical yield (in grams) of CH3CH2CH2CH₂-O-CH₂ CH2CH3 (butyl propyl ether) that can be obtained if one has available 0.75 mL of butyl alcohol (CH3CH2CH2CH2OH also called 1-butanol), 0.25 gram of sodium metal, and 0.55 mL of propyl bromide (CH3CH2CH2Br also called 1- bromopropane)? (No credit for a correct answer that does not have the (4) calculations shown and which does not include the calculations that are needed to determine the limiting reagent.) Pay attention to sig figs!!! Identify which of the possible molecules below produced the provided 13C-NMR spectra. Explain your answer. 200 H N. & NAT NH H N. IN 150 100 NH 'N' NH 'N' Н
Williamson Ether Synthesis (continued on the next page): (1) ( ©) One of the following compounds shows exactly 1 signal in its 13C NMR spectrum, another one shows 2, one shows 3, one 4, one 5, and another one shows 6 signals. Draw them in the correct ascending order; i.e., have the one with 1 signal on the left side, then the one with 2 signals, then 3, then 4, then 5, and finally, the one with 6 signals. tos रे et रे (2) (3) a) Draw the ionic product if we had used isobutyl acohol for the first reaction with sodium metal. Include all valence electrons and charges. b) What would be the byproduct of this reaction? (5) What is the theoretical yield (in grams) of CH3CH2CH2CH₂-O-CH₂ CH2CH3 (butyl propyl ether) that can be obtained if one has available 0.75 mL of butyl alcohol (CH3CH2CH2CH2OH also called 1-butanol), 0.25 gram of sodium metal, and 0.55 mL of propyl bromide (CH3CH2CH2Br also called 1- bromopropane)? (No credit for a correct answer that does not have the (4) calculations shown and which does not include the calculations that are needed to determine the limiting reagent.) Pay attention to sig figs!!! Identify which of the possible molecules below produced the provided 13C-NMR spectra. Explain your answer. 200 H N. & NAT NH H N. IN 150 100 NH 'N' NH 'N' Н
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL3: Carbon (13c) Nmr Spectroscopy
Section: Chapter Questions
Problem 14CTQ
Related questions
Question

Transcribed Image Text:Williamson Ether Synthesis (continued on the next page):
(1)
( ©) One of the following compounds shows exactly 1 signal in its 13C
NMR spectrum, another one shows 2, one shows 3, one 4, one 5, and
another one shows 6 signals. Draw them in the correct ascending order;
i.e., have the one with 1 signal on the left side, then the one with 2 signals,
then 3, then 4, then 5, and finally, the one with 6 signals.
tos
रे
et रे
(2)
(3)
a) Draw the ionic product if we had used isobutyl acohol for the first
reaction with sodium metal. Include all valence electrons and
charges.
b) What would be the byproduct of this reaction?
(5) What is the theoretical yield (in grams) of CH3CH2CH2CH₂-O-CH₂
CH2CH3 (butyl propyl ether) that can be obtained if one has available 0.75
mL of butyl alcohol (CH3CH2CH2CH2OH also called 1-butanol), 0.25 gram of
sodium metal, and 0.55 mL of propyl bromide (CH3CH2CH2Br also called 1-
bromopropane)? (No credit for a correct answer that does not have the
(4)
calculations shown and which does not include the calculations that are
needed to determine the limiting reagent.) Pay attention to sig figs!!!
Identify which of the possible molecules below produced the
provided 13C-NMR spectra. Explain your answer.
200
H
N.
& NAT
NH
H
N.
IN
150
100
NH
'N'
NH
'N'
Н
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 2 images

Recommended textbooks for you

Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning

Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning