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Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 19.SE, Problem 78AP
Tamoxifen is a drug used in the treatment of breast cancer. How would you prepare tamoxifen from benzene, the following
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Consider the following reaction:
Br
ELOH
i) How would the rate of reaction be affected if the concentration of the tert-butyl bromide
is doubled?
ii) How would the rate of reaction be affected if the concentration of the EtOH is doubled?
What are the products obtained from saponification of isopropyl benzoate with sodium hydroxide?
O Sodium propanoate + phenol
O benzoic acid + 2-propanol
O 2-Propanoic acid + benzyl acohol
O Sodium benzoate + 1-propanol
O Sodium benzoate + 2-propanol
The compound shown is the principal component of vanilla bean extracts:
H
HO
What is the IUPAC name of this compound?
O 1-formyl-3-methoxyphenol
O 3-formyl-2-methoxyphenol
O 4-hydroxy-3-methoxybenzaldehyde
O
1-hydroxy-2-methoxybenzaldehyde
O None of these
OCH 3
Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Prob. 1PCh. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3PCh. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7PCh. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9PCh. 19.8 - Show the products you would obtain by...
Ch. 19.8 - Prob. 11PCh. 19.8 - Prob. 12PCh. 19.9 - Prob. 13PCh. 19.10 - Prob. 14PCh. 19.10 - Prob. 15PCh. 19.11 - What carbonyl compound and what phosphorus ylide...Ch. 19.11 - -Carotene, a yellow food-coloring agent and...Ch. 19.12 - Prob. 18PCh. 19.12 - Prob. 19PCh. 19.13 - Prob. 20PCh. 19.13 - Treatment of 2-cyclohexenone with HCN/KCN yields a...Ch. 19.13 - How might conjugate addition reactions of lithium...Ch. 19.14 - How might you use IR spectroscopy to determine...Ch. 19.14 - Prob. 24PCh. 19.14 - Prob. 25PCh. 19.14 - Prob. 26PCh. 19.SE - Each of the following substances can be prepared...Ch. 19.SE - Prob. 28VCCh. 19.SE - Prob. 29VCCh. 19.SE - Prob. 30MPCh. 19.SE - Prob. 31MPCh. 19.SE - Prob. 32MPCh. 19.SE - Prob. 33MPCh. 19.SE - Prob. 34MPCh. 19.SE - Prob. 35MPCh. 19.SE - It is not uncommon for organic chemists to prepare...Ch. 19.SE - Prob. 37MPCh. 19.SE - Prob. 38MPCh. 19.SE - Prob. 39MPCh. 19.SE - Prob. 40MPCh. 19.SE - Aldehydes and ketones react with thiols to yield...Ch. 19.SE - Prob. 42MPCh. 19.SE - When cyclohexanone is heated in the presence of a...Ch. 19.SE - Prob. 44MPCh. 19.SE - The Meerwein-Ponndorf-Verley reaction involves...Ch. 19.SE - Propose a mechanism to account for the formation...Ch. 19.SE - Prob. 47MPCh. 19.SE - Prob. 48MPCh. 19.SE - Treatment of an , -unsaturated ketone with basic...Ch. 19.SE - Prob. 50MPCh. 19.SE - Prob. 51MPCh. 19.SE - Prob. 52MPCh. 19.SE - Prob. 53MPCh. 19.SE - Prob. 54APCh. 19.SE - Draw and name the seven aldehydes and ketones with...Ch. 19.SE - Give IUPAC names for the following compounds:Ch. 19.SE - Draw structures of compounds that fit the...Ch. 19.SE - Predict the products of the reaction of (1)...Ch. 19.SE - Show how you might use a Wittig reaction to...Ch. 19.SE - How would you use a Grignard reaction on an...Ch. 19.SE - Prob. 61APCh. 19.SE - Prob. 62APCh. 19.SE - How would you synthesize the following substances...Ch. 19.SE - Carvone is the major constituent of spearmint oil....Ch. 19.SE - How would you synthesize the following compounds...Ch. 19.SE - At what position would you expect to observe IR...Ch. 19.SE - Acidcatalyzed dehydration of...Ch. 19.SE - Choose the structure that best fits the IR...Ch. 19.SE - Propose structures for molecules that meet the...Ch. 19.SE - Prob. 70APCh. 19.SE - Prob. 71APCh. 19.SE - When 4hydroxybutanal is treated with methanol in...Ch. 19.SE - Prob. 73APCh. 19.SE - Prob. 74APCh. 19.SE - Prob. 75APCh. 19.SE - Prob. 76APCh. 19.SE - Prob. 77APCh. 19.SE - Tamoxifen is a drug used in the treatment of...Ch. 19.SE - Compound A, MW 86, shows an IR absorption at 1730...Ch. 19.SE - Compound B is isomeric with A (Problem 19-79) and...Ch. 19.SE - The 1HNMR spectrum shown is that of a compound...Ch. 19.SE - Prob. 82APCh. 19.SE - Propose structures for ketones or aldehydes that...Ch. 19.SE - Prob. 84APCh. 19.SE - Prob. 85APCh. 19.SE - The proton and carbon NMR spectra for each of...Ch. 19.SE - The proton NMR spectrum for a compound with...
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- Draw the resonance structure of the following intermediates in the nitration of phenol: OH =arrow_forwardThe following molecule belongs to a class of compounds called enediols. Each carbon of the double bond carries an —OH group: Draw structural formulas for the α-hydroxyketone and the α-hydroxyaldehyde with which this enediol is in equilibrium. α-hydroxyketone α-hydroxyaldehydearrow_forwardAcetals are formed from the reaction of two alcohols with a carbonyl under acidic conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol molecules. Choose the factor that explains the difference in reaction rates. A) The reaction with 1,2-ethanediol has a lower AH (enthalpy) of reaction. B) The reaction with 1,2-ethanediol has a higher AH (enthalpy) of reaction. C) The reaction with 1,2-ethanediol has a more favorable entropy of reaction.arrow_forward
- Write an equation for the reaction (if any) of benzaldehyde with each of the following reagents: - a) Tollen's reagent b) hydroxylamine c) ethyl magnesium bromide, then H3O+ d) phenylhydrazine e) HCN f) excess methanol, H+ g) LiAlH4 h) ethylene glycol, H+arrow_forwardDescribe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.arrow_forwardKetoprofen, like ibuprofen, is an anti-inflammatory analgesic. How can ketoprofen be synthesized from the given starting material?arrow_forward
- Predict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+arrow_forwardThe following molecule belongs to a class of compounds called enediols; each carbon of the double bond carries an-OH group. Draw structural formulas for the a-hydroxyketone and the a-hydroxyaldehyde with which this enediol is in equilibrium. CH-OH a-Hydroxyaldehyde = C-OH= a -Hydroxyketone ČH3 An enediolarrow_forwardStarting from cyclohexanone, show how to make the two given products, include conditions to use in the reactions. CH3 CH3arrow_forward
- What product is formed from the addition of NaOH to p-tertbutylphenol? Group of answer choices a compound with addition of an OH group to p-tertbutyl phenol the sodium salt of p-tertbutylphenol, sodium p-tertbutylphenoxide a protonated version of p-tertbutylphenol there is no reactionarrow_forward1. Which pair of aldehydes can lead to the following product? 10% NaOH(aq) OH H 2 moles of propanal ethanal + butanal 2 moles of ethanal ethanal + propanalarrow_forwardwhat product is formed after recrystallizing a mixture of 4-phenylcyclohexanone and 4-phenylcyclohexanol?arrow_forward
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