Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 22.8, Problem 28P
Which bonds in the backbone of a peptide can rotate freely?
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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.
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1.
2.
Answer Bank
NaH
NaOH
NaOCH,
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Write the systematic name of each organic molecule:
structure
CH3
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CH3-C-CH-CH2-CH3
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CH3
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HO—CH, CH–CH—C CH3
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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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Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - a. Explain why, when the imidazole ring of...Ch. 22.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 22.2 - Prob. 4PCh. 22.3 - Prob. 5PCh. 22.3 - Prob. 6PCh. 22.3 - Draw the predominant form for glutamate in a...Ch. 22.3 - a. Why is the pKa of the glutamate side chain...Ch. 22.4 - Explain why the pI of lysine is the average of the...Ch. 22.4 - Calculate the pI of each of the following amino...Ch. 22.4 - a. Which amino acid has the lowest pI value? b....
Ch. 22.4 - Prob. 13PCh. 22.5 - What aldehyde is formed when valine is treated...Ch. 22.5 - Prob. 15PCh. 22.5 - Prob. 16PCh. 22.5 - Prob. 17PCh. 22.5 - Prob. 18PCh. 22.6 - Why is excess ammonia used in the preceding...Ch. 22.6 - Prob. 20PCh. 22.6 - What amino acid is formed using the...Ch. 22.6 - Prob. 22PCh. 22.6 - What amino acid is formed when the aldehyde used...Ch. 22.7 - Esterase is an enzyme that catalyzes the...Ch. 22.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 22.8 - Prob. 26PCh. 22.8 - Prob. 27PCh. 22.8 - Which bonds in the backbone of a peptide can...Ch. 22.9 - What is the configuration about each of the...Ch. 22.9 - Glutathione is a tripeptide whose function is to...Ch. 22.10 - What dipeptides would be formed by heating a...Ch. 22.10 - Suppose you are trying to synthesize the dipeptide...Ch. 22.10 - Show the steps in the synthesis of the...Ch. 22.10 - a. Calculate the overall yield of bradykinin when...Ch. 22.11 - Show the steps in the synthesis of the...Ch. 22.13 - Prob. 36PCh. 22.13 - In determining the primary structure of insulin,...Ch. 22.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 22.13 - Explain why cyanogen bromide does not cleave on...Ch. 22.13 - Indicate the peptides produced from cleavage by...Ch. 22.13 - Prob. 42PCh. 22.13 - Three peptides were obtained from a trypsin...Ch. 22.14 - Prob. 44PCh. 22.15 - How would a protein that resides in the nonpolar...Ch. 22.16 - a. Which would have the greatest percentage of...Ch. 22 - Prob. 47PCh. 22 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Aspartame (its structure is on page 1007) has a pl...Ch. 22 - Draw the form of aspartate that predominates at...Ch. 22 - A professor was preparing a manuscript for...Ch. 22 - Prob. 54PCh. 22 - Determine the amino acid sequence of a polypeptide...Ch. 22 - Prob. 56PCh. 22 - Which is the more effective buffer at...Ch. 22 - Identify the location and type of charge on the...Ch. 22 - Draw the product obtained when a lysine side chain...Ch. 22 - After the polypeptide shown below was treated with...Ch. 22 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 22 - Show how aspartame can be synthesized using DCCD.Ch. 22 - -Amino acids can be prepared by treating an...Ch. 22 - Reaction of a polypeptide with carboxypeptidase A...Ch. 22 - a. How many different octapeptides can be made...Ch. 22 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 22 - A mixture of 15 amino acids gave the fingerprint...Ch. 22 - Write the mechanism for the reaction of an amino...Ch. 22 - Prob. 69PCh. 22 - Show how valine can be prepared by a. a...Ch. 22 - A chemist wanted to test his hypothesis that the...Ch. 22 - Propose a mechanism for the rearrangement of the...Ch. 22 - A normal polypeptide and a mutant of the...Ch. 22 - Determine the amino acid sequence of a polypeptide...
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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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