EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
9th Edition
ISBN: 9781305084391
Author: McMurry
Publisher: CENGAGE L
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Question
Chapter 9.SE, Problem 51AP
Interpretation Introduction
Interpretation:
Mestranol is synthesized by the reaction of a ketone with sodium acetylide in the presence of dilute acids. The structure of the ketone needed to prepare it is to be given.
Concept introduction:
When
To state:
The structure of the ketone needed to prepare mestranol by reaction with sodium acetylide in the presence of dilute acids.
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Predict the organic products that form in the reaction below:
H.
H+
+
OH
H+
Y
Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the
products.
In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the
structures in any arrangement that you like, so long as they aren't touching.
Explanation
Check
Click and drag to start drawing a
structure.
G
X
C
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+
111
Carbonyl Chem
Choosing reagants for a Wittig reaction
What would be the best choices for the missing reagents 1 and 3 in this synthesis?
1. PPh3
3
1
2
2. n-BuLi
• Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like.
Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is.
• Note: if one of your reagents needs to contain a halogen, use bromine.
Explanation
Check
Click and drag to start drawing a structure.
×
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A student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there
are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from
the arrow.
• Is the student's transformation possible? If not, check the box under the drawing area.
. If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts,
inorganic reagents, or other important reaction conditions above and below the arrow.
• You do not need to balance the reaction, but be sure every important organic reactant or product is shown.
+
T
X
O
O
лет-ле
HO
OH
HO
OH
This transformation can't be done in one step.
Chapter 9 Solutions
EP ORGANIC CHEMISTRY,24 MONTH-OWLV2
Ch. 9.1 - Prob. 1PCh. 9.1 - Prob. 2PCh. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4PCh. 9.4 - Prob. 5PCh. 9.4 - Prob. 6PCh. 9.4 - Prob. 7PCh. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P
Ch. 9.8 - Prob. 11PCh. 9.9 - Show the terminal alkyne and alkyl halide from...Ch. 9.9 - Beginning with acetylene and any alkyl halide...Ch. 9.SE - Name the following alkynes, and predict the...Ch. 9.SE - From what alkyne might each of the following...Ch. 9.SE - Prob. 16VCCh. 9.SE - The following cycloalkyne is too unstable to...Ch. 9.SE - Prob. 18MPCh. 9.SE - Assuming that strong acids add to alkynes in the...Ch. 9.SE - Prob. 20MPCh. 9.SE - Prob. 21MPCh. 9.SE - Prob. 22MPCh. 9.SE - Prob. 23MPCh. 9.SE - Prob. 24MPCh. 9.SE - Reaction of acetone with D3O+ yields...Ch. 9.SE - Give IUPAC names for the following compounds:Ch. 9.SE - Draw structures corresponding to the following...Ch. 9.SE - Prob. 28APCh. 9.SE - Prob. 29APCh. 9.SE - Prob. 30APCh. 9.SE - Predict the products from reaction of l-hexyne...Ch. 9.SE - Prob. 32APCh. 9.SE - Prob. 33APCh. 9.SE - Propose structures for hydrocarbons that give the...Ch. 9.SE - Identify the reagents a-c in the following scheme:Ch. 9.SE - Prob. 36APCh. 9.SE - Prob. 37APCh. 9.SE - Prob. 38APCh. 9.SE - How would you carry out the following...Ch. 9.SE - Prob. 40APCh. 9.SE - Synthesize the following compounds using 1-butyne...Ch. 9.SE - Prob. 42APCh. 9.SE - Prob. 43APCh. 9.SE - Prob. 44APCh. 9.SE - Prob. 45APCh. 9.SE - A hydrocarbon of unknown structure has the formula...Ch. 9.SE - Compound A(C9H12) absorbed 3 equivalents of H2 on...Ch. 9.SE - Hydrocarbon A has the formula C12H8. It absorbs 8...Ch. 9.SE - Occasionally, a chemist might need to invert the...Ch. 9.SE - Prob. 50APCh. 9.SE - Prob. 51APCh. 9.SE - Prob. 52APCh. 9.SE - Prob. 53APCh. 9.SE - Prob. 54APCh. 9.SE - Prob. 55APCh. 9.SE - Prob. 56APCh. 9.SE - Prob. 57AP
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- Determine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X Sarrow_forwardPredict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂Oarrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? H H C H- a -H b H Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal groups may have slightly different sizes. a = b = 0 °arrow_forward
- What are the angles a and b in the actual molecule of which this is a Lewis structure? :0: HCOH a Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal that might be caused by the fact that different electron groups may have slightly different sizes. a = 0 b=0° Sarrow_forwardDetermine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forward
- CH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forwardWhat would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.arrow_forwardPredict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×arrow_forward
- Predict the organic products that form in the reaction below: + OH +H H+ ➤ ☑ X - Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Garrow_forwardPredict the organic products that form in the reaction below: OH H+ H+ + ☑ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. ✓ marrow_forwardDetermine the structures of the missing organic molecules in the following reaction: + H₂O +H H+ Y Z ☑ ☑ Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X, Y, and Z. You may draw the structures in any arrangement that you like, so long as they aren't touching. Molecule X shows up in multiple steps, but you only have to draw its structure once. Click and drag to start drawing a structure. AP +arrow_forward
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