
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 21.13, Problem 37P
Interpretation Introduction
Interpretation:
The mechanism for the reaction of cysteine side chain with iodoacetic acid has to be drawn.
Concept introduction:
Cysteine amino acid has thiols group.
Iodo-group of iodoacetic acid is substituted by thiol (-SH) through
Expert Solution & Answer

Trending nowThis is a popular solution!

Students have asked these similar questions
1.
Answer the questions about the following reaction:
(a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this
reaction. Be sure to include any relevant stereochemistry in the product structure.
+
SK
F
Br
+
(b) In which solvent would this reaction proceed the fastest (Circle one)
Methanol
Acetone
(c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the
one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you
observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest
other products that are formed? Draw them in the box provided.
3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants
or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure
and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in
the reactant before being able to draw the arrows corresponding to product formation.
A.
B.
Rearrangement
ΘΗ
2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly
where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial
credit will be given. Note: You may need to draw in lone pairs before drawing the arrows.
A.
B.
H-Br
人
C
Θ
CI
H
Cl
Θ
+
Br
O
Chapter 21 Solutions
Organic Chemistry (8th Edition)
Ch. 21.1 - a. Explain why, when the imidazole ring of...Ch. 21.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 21.2 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.3 - Draw the predominant form for glutamate in a...Ch. 21.3 - a. Why is the pKa of the glutamate side chain...Ch. 21.4 - Calculate the pI of each of the following amino...Ch. 21.4 - a. Which amino acid has the lowest pI value? b....Ch. 21.4 - Prob. 12P
Ch. 21.4 - Prob. 13PCh. 21.4 - Explain why the pI of lysine is the average of the...Ch. 21.5 - What aldehyde is formed when valine is treated...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.5 - Prob. 18PCh. 21.5 - Prob. 19PCh. 21.6 - Why is excess ammonia used in the preceding...Ch. 21.6 - Prob. 21PCh. 21.6 - What amino acid is formed using the...Ch. 21.6 - Prob. 23PCh. 21.6 - What amino acid is formed when the aldehyde used...Ch. 21.7 - Esterase is an enzyme that catalyzes the...Ch. 21.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 21.8 - Draw the resonance contributors of the peptide...Ch. 21.8 - Which bonds in the backbone of a peptide can...Ch. 21.9 - An opioid pentapeptide has the following...Ch. 21.9 - What is the configuration about each of the...Ch. 21.9 - Glutathione is a tripeptide whose function is to...Ch. 21.10 - What dipeptides would be formed by heating a...Ch. 21.10 - Suppose you are trying to synthesize the dipeptide...Ch. 21.10 - Show the steps in the synthesis of the...Ch. 21.10 - a. Calculate the overall yield of bradykinin when...Ch. 21.11 - Show the steps in the synthesis of the...Ch. 21.13 - Prob. 37PCh. 21.13 - In determining the primary structure of insulin,...Ch. 21.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 21.13 - Explain why cyanogen bromide does not cleave on...Ch. 21.13 - Indicate the peptides produced from cleavage by...Ch. 21.14 - Prob. 43PCh. 21.14 - Three peptides were obtained from a trypsin...Ch. 21.14 - Prob. 45PCh. 21.15 - How would a protein that resides in the nonpolar...Ch. 21.16 - a. Which would have the greatest percentage of...Ch. 21.17 - When apples that have been cut are exposed to...Ch. 21 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 21 - Prob. 50PCh. 21 - A titration curve is a plot of the pH of a...Ch. 21 - Prob. 52PCh. 21 - Aspartame (its structure is on page 1007) has a pl...Ch. 21 - Draw the form of aspartate that predominates at...Ch. 21 - Show how phenylalanine can be prepared by...Ch. 21 - A professor was preparing a manuscript for...Ch. 21 - What aldehydes are formed when the following amino...Ch. 21 - Prob. 58PCh. 21 - Determine the amino acid sequence of a polypeptide...Ch. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Which is the more effective buffer at...Ch. 21 - Identify the location and type of charge on the...Ch. 21 - Draw the product obtained when a lysine side chain...Ch. 21 - After the polypeptide shown below was treated with...Ch. 21 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 21 - Show how aspartame can be synthesized using DCCD.Ch. 21 - -Amino acids can be prepared by treating an...Ch. 21 - Reaction of a polypeptide with carboxypeptidase A...Ch. 21 - a. How many different octapeptides can be made...Ch. 21 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 21 - A mixture of 15 amino acids gave the fingerprint...Ch. 21 - Write the mechanism for the reaction of an amino...Ch. 21 - Prob. 74PCh. 21 - Show how valine can be prepared by a. a...Ch. 21 - The primary structure of -endorphin, a peptide...Ch. 21 - A chemist wanted to test his hypothesis that the...Ch. 21 - Propose a mechanism for the rearrangement of the...Ch. 21 - A normal polypeptide and a mutant of the...Ch. 21 - Determine the amino acid sequence of a polypeptide...
Knowledge Booster
Similar questions
- 4. For the reactions below, draw the expected product. Be sure to indicate relevant stereochemistry or formal charges in the product structure. a) CI, H e b) H lux ligh Br 'Harrow_forwardArrange the solutions in order of increasing acidity. (Note that K (HF) = 6.8 x 10 and K (NH3) = 1.8 × 10-5) Rank solutions from least acidity to greatest acidity. To rank items as equivalent, overlap them. ▸ View Available Hint(s) Least acidity NH&F NaBr NaOH NH,Br NaCIO Reset Greatest acidityarrow_forward1. Consider the following molecular-level diagrams of a titration. O-HA molecule -Aion °° о ° (a) о (b) (c) (d) a. Which diagram best illustrates the microscopic representation for the EQUIVALENCE POINT in a titration of a weak acid (HA) with sodium. hydroxide? (e)arrow_forward
- Answers to the remaining 6 questions will be hand-drawn on paper and submitted as a single file upload below: Review of this week's reaction: H₂NCN (cyanamide) + CH3NHCH2COOH (sarcosine) + NaCl, NH4OH, H₂O ---> H₂NC(=NH)N(CH3)CH2COOH (creatine) Q7. Draw by hand the reaction of creatine synthesis listed above using line structures without showing the Cs and some of the Hs, but include the lone pairs of electrons wherever they apply. (4 pts) Q8. Considering the Zwitterion form of an amino acid, draw the Zwitterion form of Creatine. (2 pts) Q9. Explain with drawing why the C-N bond shown in creatine structure below can or cannot rotate. (3 pts) NH2(C=NH)-N(CH)CH2COOH This bond Q10. Draw two tautomers of creatine using line structures. (Note: this question is valid because problem Q9 is valid). (4 pts) Q11. Mechanism. After seeing and understanding the mechanism of creatine synthesis, students should be ready to understand the first half of one of the Grignard reactions presented in a past…arrow_forwardPropose a synthesis pathway for the following transformations. b) c) d)arrow_forwardThe rate coefficient of the gas-phase reaction 2 NO2 + O3 → N2O5 + O2 is 2.0x104 mol–1 dm3 s–1 at 300 K. Indicate whether the order of the reaction is 0, 1, or 2.arrow_forward
- 8. Draw all the resonance forms for each of the following molecules or ions, and indicate the major contributor in each case, or if they are equivalent. (4.5 pts) (a) PH2 سمةarrow_forward3. Assign absolute configuration (Rors) to each chirality center. a. H Nitz C. он b. 0 H-C. C H 7 C. ་-4 917-417 refs H 1つ ८ ડુ d. Но f. -2- 01 Ho -OH 2HNarrow_forwardHow many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red. Note for advanced students: In this question, any multiplet is counted as one signal. Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in top molecule For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. No additional Hs to color in bottom moleculearrow_forward
- In the drawing area below, draw the major products of this organic reaction: 1. NaOH ? 2. CH3Br If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. No reaction. Click and drag to start drawing a structure. ☐ : A คarrow_forwardPredict the major products of the following organic reaction: NC Δ ? Some important Notes: • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. • Be sure to draw bonds carefully to show important geometric relationships between substituents. Note: if your answer contains a complicated ring structure, you must use one of the molecular fragment stamps (available in the menu at right) to enter the ring structure. You can add any substituents using the pencil tool in the usual way. Click and drag to start drawing a structure. Х аarrow_forwardPredict the major products of this organic reaction. Be sure you use dash and wedge bonds to show stereochemistry where it's important. + ☑ OH 1. TsCl, py .... 文 P 2. t-BuO K Click and drag to start drawing a structure.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage LearningOrganic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,

Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning

Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning


General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning

Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,