Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 9, Problem 9.7P
Name each
a.
(two ways) b. 
c. 
(two ways)
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Macmillan Learning
One of the molecules shown can be made using the Williamson ether synthesis. Identify the ether and draw the
starting materials.
А
со
C
Strategy: Review the reagents, mechanism and steps of the Williamson ether synthesis. Determine which of the molecules
can be made using the steps. Then analyze the two possible disconnection strategies and deduce the starting materials.
Identify the superior route.
Step 6: Put it all together.
Complete the two-step synthesis by selecting the reagents and starting materials.
C
1.
2.
Answer Bank
NaH
NaOH
NaOCH,
снен, сен, он
Сиси, Сне
(СН), СОН
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Write the systematic name of each organic molecule:
structure
CH3
O
CH3-CH-CH-C-CH3
OH
HV.
CH3-C-CH-CH2-CH3
OH
CH3
O
HO—CH, CH–CH—C CH3
OH
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name
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Organic Functional Groups
Predicting the reactants or products of esterification
What is the missing reactant in this organic reaction?
HO
OH
H
+回
+ H₂O
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Specifically, in the drawing area below draw the skeletal ("line") structure of R.
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Chapter 9 Solutions
Organic Chemistry-Package(Custom)
Ch. 9 - Draw all constitutional isomers having molecular...Ch. 9 - Prob. 9.2PCh. 9 - Give the IUPAC name for each compound.Ch. 9 - Problem 9.3 Give the structure corresponding to...Ch. 9 - Prob. 9.5PCh. 9 - Name CH33COCH3, a gasoline additive commonly...Ch. 9 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9 - Problem 9.6 Rank the following compounds in order...Ch. 9 - Which mechanism is favored by the use of crown...Ch. 9 - Draw the organic product of each reaction.
Ch. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.17PCh. 9 - Explain how the reaction of CH32CHCHCl CH3 with...Ch. 9 - Prob. 9.19PCh. 9 - Draw the products of each reaction, indicating the...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.22PCh. 9 - Prob. 9.23PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Draw the products of each reaction, and include...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Prob. 9.29PCh. 9 - Prob. 9.30PCh. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Prob. 9.32PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.37PCh. 9 - a. Draw the structure of 1, 2, and 3 alcohol with...Ch. 9 - Give IUPAC name for each alcohol. a....Ch. 9 - Name each ether and epoxide. a.b.c.d.Ch. 9 - Prob. 9.41PCh. 9 - Draw the eight constitutional isomers with...Ch. 9 - Rank each group of compounds in order of: a....Ch. 9 - Prob. 9.44PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - Draw the organic products formed when CH3CH2CH2OH...Ch. 9 - Draw the organic products formed when 1-methyl...Ch. 9 - What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.49PCh. 9 - Prob. 9.50PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - Prob. 9.52PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - Prob. 9.57PCh. 9 - When CH3CH2CH2CH2OH is treated with H2SO4 NaBr,...Ch. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.60PCh. 9 - Draw two different routes to each of the following...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.66PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.69PCh. 9 - Devise a stepwise mechanism for the following...Ch. 9 - Draw the products of each reaction, and indicate...Ch. 9 - Prepare each compound from CH3CH2CH2CH2OH. More...Ch. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.75PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.77PCh. 9 - Prob. 9.78PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - Dehydration of 1, 2, 2-trimethylcyclohexanol with...Ch. 9 - Prob. 9.81PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 -
9.81 Aziridines are heterocycles that contain an...
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- Please help me with number 5 using my data and graph. I think I might have number 3 and 4 but if possible please check me. Thanks in advance!arrow_forwarddict the major products of this organic reaction. C Explanation Check 90 + 1.0₂ 3 2. (CH3)2S Click and drag f drawing a stru © 2025 McGraw Hill LLC. All Rights Reserved. • 22 4 5 7 8 Y W E R S F H Bilarrow_forwardcan someone draw out the reaction mechanism for this reaction showing all the curly arrows and 2. Draw the GPNA molecule and identify the phenylalanine portion. 3. Draw L-phenylalanine with the correct stereochemistryarrow_forward
- What is the reaction mechanism for this?arrow_forwardPredict the major products of both organic reactions. Be sure to use wedge and dash bonds to show the stereochemistry of the products when it's important, for example to distinguish between two different major products. esc esc Explanation Check 2 : + + X H₁₂O + Х ง WW E R Y qab Ccaps lock shift $ P X Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility Bil T FR F18 9 G t K L Z X V B N M control opption command command T C darrow_forwardDraw the Markovnikov product of the hydrohalogenation of this alkene. this problem. Note for advanced students: draw only one product, and don't worry about showing any stereochemistry. Drawing dash and wedge bonds has been disabled for caps lock Explanation Check 2 W E R + X 5 HCI Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility Bil Y F G H K L ZZ X C V B N M control opption command F10 F10 command 4 BA Ar Carrow_forward
- I don't understand why the amide on the top left, with the R attached to one side, doesn't get substituted with OH to form a carboxylic acid. And if only one can be substituted, why did it choose the amide it chose rather than the other amide?arrow_forwardesc Draw the Markovnikov product of the hydration of this alkene. Note for advanced students: draw only one product, and don't worry about showing any stereochemistry. Drawing dash and wedge bonds has been disabled for this problem. Explanation Check BBB + X 0 1. Hg (OAc)2, H₂O 2. Na BH 5 Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility Bl P 豆 28 2 28 N 9 W E R T Y A S aps lock G H K L Z X C V B N M T central H command #e commandarrow_forwardC A student proposes the transformation below in one step of an organic synthesis. There may be one or more products missing from the right-hand side, but there are no reagents missing from the left-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 products to the right-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. (X) This transformation can't be done in one step. + Tarrow_forward
- く Predict 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. Explanation Check OH + + ✓ 2 H₂SO 4 O xs H₂O 2 Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centerarrow_forwardDraw the skeletal ("line") structure of 1,3-dihydroxy-2-pentanone. Click and drag to start drawing a structure. X Parrow_forwardPredicting edict 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. Explanation Check HO Na O H xs H₂O 2 Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center Iarrow_forward
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