Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 2, Problem 17CTQ
Interpretation Introduction
Interpretation:Non-legitimate Lewis structure from CTQ 13 should be identified by giving reasons.
Concept introduction:A Lewis structure is diagrammatic view of a molecule, where lone pair of electrons is represented in dots, bonds are represented with lines & formal charge of each atom is mentioned near the atom.
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C. I, II, III
Consider the reaction sequence below to answer the following questions:
0
0
1. NaOEt, EtOH
ΕΙΟ
OEt
2
Compound X
CO₂Et
NaOEt, EtOH
CO₂Et
Br
Compound Y
A
Compound Z
A. Compound X, diethyl propanedioate, is more commonly known as
a. ethyl acetoacetate
acetoacetic ester
b.
C.
oxalic ester
d. malonic ester
B. Write the complete stepwise mechanism for the conversion of Compound X into Compound Y.
Show all electron flow with arrows and draw all intermediate structures.
Diethyl malonate can be prepared by the following reaction sequence. Draw the structures of each of
the missing intermediates in the boxes provided
EtO
0
H3C
11
C
1. Br₂ PBr
OH 2 H₂O
010
0
CH3CH₂OH
C
CH2
OEt
Ha
CH3CH2OH
на
NaCN
H₂SO4
NC
H₂O, heat
CH2
OCH2CH3
Show how you would accomplish each of the following transformations. More than one step may be
quired. Show all reagents and all intermediate structures. [three only]
A.
0
CH3
B.
C.
D.
H
0
0
OCH 3
CH₂CO₂CH2CH3
H3C
➤ HN C
NO₂
Cl
Chapter 2 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 2 - Prob. 1CTQCh. 2 - The valence shell of an atom in a legitimate Lewis...Ch. 2 - Prob. 3CTQCh. 2 - Prob. 4CTQCh. 2 - Prob. 5CTQCh. 2 - It is impossible to draw a legitimate Lewis...Ch. 2 - Describe how to calculate the total number of...Ch. 2 - Prob. 8CTQCh. 2 - Prob. 9CTQCh. 2 - Prob. 10CTQ
Ch. 2 - Prob. 11CTQCh. 2 - Prob. 12CTQCh. 2 - A complete Lewis structure must show all nonzero...Ch. 2 - Prob. 14CTQCh. 2 - Prob. 15CTQCh. 2 - Prob. 16CTQCh. 2 - Prob. 17CTQCh. 2 - Prob. 18CTQCh. 2 - Complete the rest of the table for N, O or X by...Ch. 2 - Prob. 20CTQCh. 2 - Prob. 21CTQCh. 2 - Make a checklist that can be used to determine if...Ch. 2 - Prob. 2ECh. 2 - Prob. 3ECh. 2 - Draw the Lewis structure of a neutral molecule...Ch. 2 - Prob. 5ECh. 2 - For each element, predict (and draw a Lewis...Ch. 2 - Predict which of the following species is least...Ch. 2 - The molecules BH3 and SF6 and the ion SO42 exist...Ch. 2 - These are NOTlegitimate Lewisstructures (and...Ch. 2 - Fill in missing formal charges where needed (all...Ch. 2 - Below each structure in the previous question is a...Ch. 2 - Prob. 12ECh. 2 - Carbon monoxide (CO) is an example of an overall...Ch. 2 - Explain why this Lewis structure for CO is not as...Ch. 2 - Prob. 15ECh. 2 - Prob. 16ECh. 2 - Prob. 17ECh. 2 - Prob. 18ECh. 2 - Prob. 19E
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