Principles of General, Organic, Biological Chemistry
2nd Edition
ISBN: 9780073511191
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Question
Chapter 13, Problem 13.49UKC
Interpretation Introduction
Interpretation:
Reason for primary
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Answer
2. Provide a clear arrow-pushing mechanism for the following reactions. Do not skip proton
transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted
without ambiguity.
a.
CH3
Ph
OEt
هد
Ph
CH3
Hint: the species on the left is an ynolate, which behaves a lot like an enolate.
b.
CH3
H3C
CH3
CH3
H3C
an unexpected product,
containing a single 9-
membered ring
the expected product,
containing two fused rings
H3C-I
(H3C)2CuLi
an enolate
Chapter 13 Solutions
Principles of General, Organic, Biological Chemistry
Ch. 13.1 - Draw out each compound to clearly show what groups...Ch. 13.1 - Prob. 13.2PCh. 13.2 - Prob. 13.3PCh. 13.2 - Give the structure corresponding to each IUPAC...Ch. 13.2 - Prob. 13.5PCh. 13.2 - Give the structure corresponding to each name. a....Ch. 13.3 - Which compound in each pair has the higher boiling...Ch. 13.3 - Rank the following compounds in order of...Ch. 13.4 - Which compounds are -hydroxy acids? tartaric acid...Ch. 13.4 - Prob. 13.10P
Ch. 13.5 - Prob. 13.11PCh. 13.5 - Prob. 13.12PCh. 13.5 - Prob. 13.13PCh. 13.6 - Prob. 13.14PCh. 13.6 - Prob. 13.15PCh. 13.6 - Prob. 13.16PCh. 13.6 - Prob. 13.17PCh. 13.6 - Prob. 13.18PCh. 13.6 - Prob. 13.19PCh. 13.7 - Prob. 13.20PCh. 13.7 - Prob. 13.21PCh. 13.7 - Prob. 13.22PCh. 13.7 - Prob. 13.23PCh. 13.7 - Prob. 13.24PCh. 13.8 - Prob. 13.25PCh. 13.8 - Prob. 13.26PCh. 13.8 - Prob. 13.27PCh. 13.8 - Draw the product formed when each ammonium salt is...Ch. 13.8 - Prob. 13.29PCh. 13.9 - Prob. 13.30PCh. 13.9 - Prob. 13.31PCh. 13.9 - Prob. 13.32PCh. 13.9 - Why is the boiling point of CH3CONH2(221C) higher...Ch. 13.9 - Prob. 13.34PCh. 13.9 - Prob. 13.35PCh. 13.10 - Prob. 13.36PCh. 13 - Prob. 13.37UKCCh. 13 - Prob. 13.38UKCCh. 13 - Prob. 13.39UKCCh. 13 - Prob. 13.40UKCCh. 13 - Prob. 13.41UKCCh. 13 - Prob. 13.42UKCCh. 13 - Prob. 13.43UKCCh. 13 - Prob. 13.44UKCCh. 13 - Prob. 13.45UKCCh. 13 - Prob. 13.46UKCCh. 13 - Prob. 13.47UKCCh. 13 - Prob. 13.48UKCCh. 13 - Prob. 13.49UKCCh. 13 - Prob. 13.50UKCCh. 13 - Prob. 13.51APCh. 13 - Prob. 13.52APCh. 13 - Prob. 13.53APCh. 13 - Draw the structure of a compound of molecular...Ch. 13 - Prob. 13.55APCh. 13 - Prob. 13.56APCh. 13 - Give an acceptable name for each compound.Ch. 13 - Prob. 13.58APCh. 13 - Prob. 13.59APCh. 13 - Prob. 13.60APCh. 13 - Prob. 13.61APCh. 13 - Prob. 13.62APCh. 13 - Prob. 13.63APCh. 13 - Give an acceptable name for each amine or amide....Ch. 13 - Draw the structure corresponding to each name. a....Ch. 13 - Draw the structure corresponding to each name. a....Ch. 13 - Prob. 13.67APCh. 13 - Draw the structure of each amine or ammonium salt....Ch. 13 - Prob. 13.69APCh. 13 - Which compound in each pair is more water soluble?...Ch. 13 - Prob. 13.71APCh. 13 - Prob. 13.72APCh. 13 - Prob. 13.73APCh. 13 - Prob. 13.74APCh. 13 - Prob. 13.75APCh. 13 - Prob. 13.76APCh. 13 - Prob. 13.77APCh. 13 - Prob. 13.78APCh. 13 - Prob. 13.79APCh. 13 - Prob. 13.80APCh. 13 - Prob. 13.81APCh. 13 - Prob. 13.82APCh. 13 - Prob. 13.83APCh. 13 - Prob. 13.84APCh. 13 - Prob. 13.85APCh. 13 - Prob. 13.86APCh. 13 - Prob. 13.87APCh. 13 - Draw the products of each acid-base reaction.Ch. 13 - Prob. 13.89APCh. 13 - Prob. 13.90APCh. 13 - Prob. 13.91APCh. 13 - Prob. 13.92APCh. 13 - Ritalin is the trade name for methylphenidate, a...Ch. 13 - Prob. 13.94APCh. 13 - Prob. 13.95CPCh. 13 - Prob. 13.96CPCh. 13 - Prob. 13.97CPCh. 13 - Prob. 13.98BTCCh. 13 - Prob. 13.99BTCCh. 13 - Prob. 13.100BTC
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Similar questions
- b. H3C CH3 1. 2. H3O+ H3C MgBr H3Carrow_forwardPredict the major products of this reaction: excess H+ NaOH ? A Note that the first reactant is used in excess, that is, there is much more of the first reactant than the second. If there won't be any products, just check the box under the drawing area instead. Explanation Check Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privarrow_forward1. 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 CH3arrow_forward
- 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 | Parrow_forwardWhat is the total energy cost associated with the compound below adopting the shown conformation? CH3 HH DH CH3arrow_forwardΗΝ, Draw Final Product C cyclohexanone pH 4-5 Edit Enamine H3O+ CH3CH2Br THF, reflux H Edit Iminium Ionarrow_forward
- How 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_forwardIdentify 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_forward
- H 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_forwardRank the following compounds in order of decreasing dipole moment. |>||>||| ||>|||>| |>|||>|| |||>||>| O ||>>||| H F H F H c=c || H c=c F F IIIarrow_forward
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