Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 25, Problem 25.41P
Varenicline (trade name Chantix) is a drug used to help smokers quit their habit. (a) Which
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1. For each of the reaction "railroads" below, you are either asked to give the structure(s) of the starting
material(s) or product(s), or provide reagents/conditions to accomplish the transformation, as
indicated by the boxes.
a.
NaOMe
H+
.CO,H
HO₂C
MeOH (excess)
MeOH
H3C
Br
يع
CH3
1. LiAlH4
2. H3O+
3. PBг3
H3C
1. Et-Li
2. H3O+
-CO₂Me
-CO₂Me
OH
CH3
CH3
ল
CH3
Predict the intermediate 1 and final product 2 of this organic reaction:
NaOMe
ག1, ད།་, -
+
H
You can draw 1 and 2 in any arrangement you like.
2
work up
Note: if either 1 or 2 consists of a pair of enantiomers, just draw one structure using line bonds instead of 3D (dash and wedge)
bonds at the chiral center.
Explanation
Check
Click and drag to start drawing a structure.
Х
© 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | P
What is the total energy cost associated with the compound below adopting the shown conformation?
CH3
HH
DH
CH3
Chapter 25 Solutions
Organic Chemistry
Ch. 25 - Prob. 25.1PCh. 25 - Draw the structure of a compound of molecular...Ch. 25 - Prob. 25.3PCh. 25 - Prob. 25.4PCh. 25 - Prob. 25.5PCh. 25 - Arrange the compounds in order of increasing...Ch. 25 - Prob. 25.7PCh. 25 - Prob. 25.8PCh. 25 - Problem 25.7
Draw the product of each...Ch. 25 - Prob. 25.10P
Ch. 25 - Prob. 25.11PCh. 25 - Prob. 25.12PCh. 25 - Prob. 25.13PCh. 25 - Prob. 25.14PCh. 25 - Prob. 25.15PCh. 25 - Prob. 25.16PCh. 25 - Prob. 25.17PCh. 25 - Prob. 25.18PCh. 25 - Draw the products of each acidbase reaction....Ch. 25 - Prob. 25.20PCh. 25 - Prob. 25.21PCh. 25 - Prob. 25.22PCh. 25 - Prob. 25.23PCh. 25 - Problem 25.22
Which nitrogen atom in each compound...Ch. 25 - Which N atom in each drug is more basic? a. b. c.Ch. 25 - Prob. 25.26PCh. 25 - Prob. 25.27PCh. 25 - Prob. 25.28PCh. 25 - Prob. 25.29PCh. 25 - Prob. 25.30PCh. 25 - Problem 25.28
Draw the major product formed in...Ch. 25 - Prob. 25.32PCh. 25 - Prob. 25.33PCh. 25 - Problem 25.31
Devise a synthesis of each compound...Ch. 25 - Prob. 25.35PCh. 25 - Problem 25.33
What starting materials are needed...Ch. 25 - Problem 25.34
(a) What two components are needed...Ch. 25 - Prob. 25.38PCh. 25 - Prob. 25.39PCh. 25 - Prob. 25.40PCh. 25 - 25.37 Varenicline (trade name Chantix) is a drug...Ch. 25 - Prob. 25.42PCh. 25 - Prob. 25.43PCh. 25 - Prob. 25.44PCh. 25 - Prob. 25.45PCh. 25 - Prob. 25.46PCh. 25 - Prob. 25.47PCh. 25 - Prob. 25.48PCh. 25 - Decide which N atom in each molecule is most basic...Ch. 25 - 25.44 Rank the nitrogen atoms in each compound in...Ch. 25 - 25.45 Explain why nitroaniline is a stronger base...Ch. 25 - 25.46 Explain the observed difference in the...Ch. 25 - 25.47 Why is pyrrole more acidic than...Ch. 25 - How would you prepare 3-phenyl-1-propanamine...Ch. 25 - Prob. 25.55PCh. 25 - Prob. 25.56PCh. 25 - Prob. 25.57PCh. 25 - Prob. 25.58PCh. 25 - 25.51 How would you separate toluene , benzoic...Ch. 25 - 25.52 Draw the products formed when methylaniline ...Ch. 25 - Prob. 25.61PCh. 25 - Prob. 25.62PCh. 25 - Prob. 25.63PCh. 25 - Prob. 25.64PCh. 25 - Prob. 25.65PCh. 25 - Prob. 25.66PCh. 25 - Prob. 25.67PCh. 25 - Prob. 25.68PCh. 25 - 25.60 A chiral amine A having the configuration...Ch. 25 - 25.61 Draw a stepwise mechanism for each...Ch. 25 - 25.62 Draw a stepwise mechanism for the following...Ch. 25 - Prob. 25.72PCh. 25 - Tertiary (3) aromatic amines react with NaNO2 and...Ch. 25 - Prob. 25.74PCh. 25 - Devise a synthesis of each compound from benzene....Ch. 25 - Prob. 25.76PCh. 25 - Prob. 25.77PCh. 25 - Prob. 25.78PCh. 25 - Prob. 25.79PCh. 25 - Synthesize each compound from benzene. Use a...Ch. 25 - Prob. 25.81PCh. 25 - Devise a synthesis of each compound from benzene,...Ch. 25 - Prob. 25.83PCh. 25 - 25.72 Three isomeric compounds A, B, and C, all...Ch. 25 - 25.73 Treatment of compound D with LiAlH4 followed...Ch. 25 - Prob. 25.86PCh. 25 - 25.75 Rank the following compounds in order of...Ch. 25 - Prob. 25.88PCh. 25 - Prob. 25.89PCh. 25 - Prob. 25.90P
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- ΗΝ, Draw Final Product C cyclohexanone pH 4-5 Edit Enamine H3O+ CH3CH2Br THF, reflux H Edit Iminium Ionarrow_forwardHow many hydrogen atoms are connected to the indicated carbon atom?arrow_forwardIdentify the compound with the longest carbon - nitrogen bond. O CH3CH2CH=NH O CH3CH2NH2 CH3CH2C=N CH3CH=NCH 3 The length of all the carbon-nitrogen bonds are the samearrow_forward
- Identify any polar covalent bonds in epichlorohydrin with S+ and 8- symbols in the appropriate locations. Choose the correct answer below. Η H's+ 6Η Η Η Η Η Ηδ Η Ο Ο HH +Η Η +Η Η Η -8+ CIarrow_forwardH H:O::::H H H HH H::O:D:D:H HH HH H:O:D:D:H .. HH H:O:D:D:H H H Select the correct Lewis dot structure for the following compound: CH3CH2OHarrow_forwardRank the following compounds in order of decreasing boiling point. ннннн -С-С-Н . н-с- ННННН H ΗΤΗ НННН TTTĪ н-с-с-с-с-о-н НННН НН C' Н н-с-с-с-с-н НН || Ш НННН H-C-C-C-C-N-H ННННН IVarrow_forward
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- What is the approximate bond angle around the nitrogen atom? HNH H Harrow_forwardOH 1. NaOCH2CH3 Q 2. CH3CH2Br (1 equiv) H3O+ Select to Draw 1. NaOCH2 CH3 2. CH3Br (1 equiv) heat Select to Edit Select to Drawarrow_forwardComplete and balance the following half-reaction in acidic solution. Be sure to include the proper phases for all species within the reaction. S₂O₃²⁻(aq) → S₄O₆²⁻(aq)arrow_forward
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