EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220100591310
Author: McMurry
Publisher: CENGAGE L
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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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Analyze the following reaction by looking at the electron configurations given below each box.
Put a number and a symbol in each box to show the number and kind of the corresponding atom or ion.
Use the smallest integers possible.
cation
anion
+
+
Shell 1: 2
Shell 2: 8
Shell 3: 1
Shell 1 : 2
Shell 2 : 6
Shell 1 : 2
Shell 2: 8
Shell 1: 2
Shell 2: 8
None
IV.
Show the detailed synthesis strategy for the following compounds.
a. CH3CH2CH2CH2Br
CH3CH2CCH2CH2CH3
Chapter 19 Solutions
EBK 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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- Do the electrons on the OH participate in resonance with the ring through a p orbital? How many pi electrons are in the ring, 4 (from the two double bonds) or 6 (including the electrons on the O)?arrow_forwardPredict and draw the product of the following organic reaction:arrow_forwardNonearrow_forward
- Redraw the molecule below as a skeletal ("line") structure. Be sure to use wedge and dash bonds if necessary to accurately represent the direction of the bonds to ring substituents. Cl. Br Click and drag to start drawing a structure. : ☐ ☑ Parrow_forwardK m Choose the best reagents to complete the following reaction. L ZI 0 Problem 4 of 11 A 1. NaOH 2. CH3CH2CH2NH2 1. HCI B OH 2. CH3CH2CH2NH2 DII F1 F2 F3 F4 F5 A F6 C CH3CH2CH2NH2 1. SOCl2 D 2. CH3CH2CH2NH2 1. CH3CH2CH2NH2 E 2. SOCl2 Done PrtScn Home End FA FQ 510 * PgUp M Submit PgDn F11arrow_forwardNonearrow_forward
- Add curved arrows to the reactants in this reaction. A double-barbed curved arrow is used to represent the movement of a pair of electrons. Draw curved arrows. : 0: si H : OH :: H―0: Harrow_forwardConsider this step in a radical reaction: Br N O hv What type of step is this? Check all that apply. Draw the products of the step on the right-hand side of the drawing area below. If more than one set of products is possible, draw any set. Also, draw the mechanism arrows on the left-hand side of the drawing area to show how this happens. O primary Otermination O initialization O electrophilic O none of the above × ☑arrow_forwardNonearrow_forward
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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY