Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.53P
Identify the lettered compounds in the following reaction scheme. Compounds F, G, and K are isomers of molecular formula C13H18O. How could 1H NMR spectroscopy distinguish these three compounds from each other?
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Don't used hand raiting
It is not unexpected that the methoxyl substituent on a cyclohexane ring
prefers to adopt the equatorial conformation.
OMe
H
A G₂ = +0.6 kcal/mol
OMe
What is unexpected is that the closely related 2-methoxytetrahydropyran
prefers the axial conformation:
H
H
OMe
OMe
A Gp=-0.6 kcal/mol
Methoxy: CH3O group
Please be specific and clearly write the reason why this is observed. This effect that provides
stabilization of the axial OCH 3 group in this molecule is called the anomeric effect. [Recall in the way of
example, the staggered conformer of ethane is more stable than eclipsed owing to bonding MO
interacting with anti-bonding MO...]
206 Pb
82
Express your answers as integers. Enter your answers separated by a comma.
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VAΣ
ΜΕ ΑΣΦ
Np, N₁ = 82,126
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protons, neutrons
Chapter 20 Solutions
Organic Chemistry-Package(Custom)
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Draw the structure of both an acid chloride and an...Ch. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - What product is formed when...Ch. 20 - Prob. 20.16PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Draw the product formed when each organometallic...Ch. 20 - Draw the product of each reaction. a.c. b.d.Ch. 20 - Draw the products including stereochemistry of the...Ch. 20 - What Grignard reagent and carbonyl compound are...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organocuprate reagent is needed to convert...Ch. 20 - What reagent is needed to convert (CH3)2CHCH2CHO...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - Prob. 20.39PCh. 20 - Draw the product formed when CH3CH2CH2MgBr is...Ch. 20 - Draw the product formed when (CH3CH2CH2CH2)2CuLi...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.43PCh. 20 - What reagent is needed to convert...Ch. 20 - What reagent is needed to convert...Ch. 20 - Draw the products or each reduction reaction. a....Ch. 20 - Prob. 20.47PCh. 20 - Draw all stereoisomers formed in each reaction. a....Ch. 20 - Prob. 20.49PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.52PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.54PCh. 20 - Draw a stepwise mechanism for each reaction. a. b.Ch. 20 - Prob. 20.56PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - What Grignard reagent and aldehyde or ketone are...Ch. 20 - Prob. 20.59PCh. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organolithium reagent and carbonyl compound...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.63PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - Synthesize each compound from cyclohexanol using...Ch. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Devise three different methods to prepare each...Ch. 20 - Convert benzene into each compound. You may also...Ch. 20 - Design a synthesis of each compound from alcohols...Ch. 20 - Synthesize each compound from the given starting...Ch. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.84P
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