ORGANIC CHEM W/BIOLOGICAL TOP. ACCESS
6th Edition
ISBN: 9781264382545
Author: SMITH
Publisher: MCG CUSTOM
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Chapter 18.1, Problem 2P
Interpretation Introduction
Interpretation: An explanation for the less reactivity of benzaldehyde than cyclohexanecarbaldehyde towards nucleophilic attack is to be stated.
Concept introduction: Both
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What are the IUPAC Names of all the compounds in the picture?
1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following
compounds. Please show your work. (8) SF2, CH,OH, C₂H₂
b) Based on your answers given above, list the compounds in order of their Boiling Point
from low to high. (8)
19.78 Write the products of the following sequences of reactions. Refer to your reaction road-
maps to see how the combined reactions allow you to "navigate" between the different
functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18
roadmaps along with your new Chapter 19 roadmap for these.
(a)
1. BHS
2. H₂O₂
3. H₂CrO4
4. SOCI₂
(b)
1. Cl₂/hv
2. KOLBU
3. H₂O, catalytic H₂SO4
4. H₂CrO4
Reaction
Roadmap
An alkene 5. EtOH
6.0.5 Equiv. NaOEt/EtOH
7. Mild H₂O
An alkane
1.0
2. (CH3)₂S
3. H₂CrO
(d)
(c)
4. Excess EtOH, catalytic H₂SO
OH
4. Mild H₂O*
5.0.5 Equiv. NaOEt/EtOH
An alkene 6. Mild H₂O*
A carboxylic
acid
7. Mild H₂O*
1. SOC₁₂
2. EtOH
3.0.5 Equiv. NaOEt/E:OH
5.1.0 Equiv. NaOEt
6.
NH₂
(e)
1. 0.5 Equiv. NaOEt/EtOH
2. Mild H₂O*
Br
(f)
i
H
An aldehyde
1. Catalytic NaOE/EtOH
2. H₂O*, heat
3. (CH,CH₂)₂Culi
4. Mild H₂O*
5.1.0 Equiv. LDA
Br
An ester
4. NaOH, H₂O
5. Mild H₂O*
6. Heat
7.
MgBr
8. Mild H₂O*
7. Mild H₂O+
Chapter 18 Solutions
ORGANIC CHEM W/BIOLOGICAL TOP. ACCESS
Ch. 18.1 - Rank the following compounds in order of...Ch. 18.1 - Prob. 2PCh. 18.2 - Give the IUPAC name for each aldehyde.Ch. 18.2 - Prob. 4PCh. 18.2 - Give the IUPAC name for each ketone.Ch. 18.5 - Prob. 11PCh. 18.9 - Problem 21.17 Draw the products of the following...Ch. 18.9 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 18.9 - Problem 21.19 Draw the products (including...Ch. 18.9 - Problem 21.20 What starting materials are needed...
Ch. 18.9 - Prob. 19PCh. 18.10 - Problem 21.22 The product formed when reacts with...Ch. 18.10 - Prob. 21PCh. 18.11 - Prob. 22PCh. 18.11 - Prob. 23PCh. 18.11 - Prob. 24PCh. 18.12 - Prob. 25PCh. 18.12 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 18.13 - Problem 21.29 Draw the products of each...Ch. 18 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 18 - 21.41 Rank the following compounds in order of...Ch. 18 - Prob. 39PCh. 18 - 21.43 Give the IUPAC name for each compound.
a....Ch. 18 - 21.44 Give the structure corresponding to each...Ch. 18 - Prob. 42PCh. 18 - 21.46 Draw the products of each reaction.
a. e....Ch. 18 - Prob. 44PCh. 18 - 21.48 Draw all stereoisomers formed in each...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Devise a synthesis of each alkene using a Wittig...Ch. 18 - Prob. 60PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - 21.64 Draw a stepwise mechanism for the following...Ch. 18 - 21.65 Draw a stepwise mechanism f or the following...Ch. 18 - Prob. 67PCh. 18 - 21.67 Draw a stepwise mechanism for each...Ch. 18 - Prob. 69PCh. 18 - Prob. 70P
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