EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 17, Problem 53P
Why is proline never found in an α-helix?
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Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of a-hydroxycarboxylic acids from ketones
and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic
acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a
cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
HO
H
HCEN
H-3-
HO'
NaOH
HO
cyanohychin
a.
a nucleophilic substitution
b.
an electrophilic addition
C10
OH
CH-COOH
A. The reaction of an aldehyde with hydrogen cyanide is an example of
+ NaCN + H₂O
reaction.
H-
C.
an electrophilic substitution
d. a nucleophilic addition
B. Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.
Refer to the data below to answer the following questions:
The octapeptide saralasin is a specific antagonist of angiotensin II. A derivative of saralasin is used
therapeutically as an antihypertensive. Amino acid analysis of saralasin show the presence of the following
amino acids:
Ala, Arg, His, Pro, Sar, Tyr, Val, Val
A. Sar is the abbreviation for sarcosine, N-methyl aminoethanoic acid. Draw the structure of sarcosine.
B. N-Terminal analysis by the Edman method shows saralasin contains sarcosine at the N-terminus.
Partial hydrolysis of saralasin with dilute hydrochloric acid yields the following fragments:
Tyr-Val-His
Sar-Arg-Val
His-Pro-Ala
Val-Tyr-Val
Arg-Val-Tyr
What is the structure of saralasin?
Give the major organic product(s) of each of the following reactions or sequences of reactions. Show
all relevant stereochemistry.[4 only]
CH3
A.
B.
HNO
H₂Pt
H₂SO4 hano
NaN
1. LIAH ether
Br
4
2 H₂O
C.
D.
E.
CH3CH2-CH2CH3 + HCl
Br
NH₂
CH3
ON
CH-CH3
Br HNOZ CUCI
11,504
HC)
1. HNO H SO
NH₂
2
UM
Chapter 17 Solutions
EBK ESSENTIAL ORGANIC CHEMISTRY
Ch. 17.1 - a. Explain why, when the imidazole ring of...Ch. 17.2 - Prob. 2PCh. 17.3 - Prob. 3PCh. 17.3 - Prob. 4PCh. 17.3 - Prob. 6PCh. 17.4 - Calculate the pI of each of the following amino...Ch. 17.4 - a. Which amino acid has the lowest pI value? b....Ch. 17.5 - What aldehyde is formed when valine is treated...Ch. 17.5 - Prob. 10PCh. 17.5 - Prob. 11P
Ch. 17.5 - Prob. 12PCh. 17.6 - Prob. 13PCh. 17.6 - What amino acid would be formed using the...Ch. 17.6 - What amino acid would be formed when the aldehyde...Ch. 17.7 - Pig liver esterase is an enzyme that catalyzes the...Ch. 17.8 - Prob. 17PCh. 17.8 - Prob. 18PCh. 17.8 - Prob. 19PCh. 17.8 - Prob. 20PCh. 17.10 - Prob. 21PCh. 17.10 - Prob. 22PCh. 17.10 - Why does cyanogen bromide not cleave on the C-side...Ch. 17.10 - Prob. 24PCh. 17.10 - Prob. 26PCh. 17.12 - Prob. 27PCh. 17.13 - a. Which would have the greatest percentage of...Ch. 17 - Draw the predominant form of the following amino...Ch. 17 - What is the pI of serine?Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Which would have a higher percentage of negative...Ch. 17 - Draw the form of aspartate that predominates at...Ch. 17 - Prob. 35PCh. 17 - A professor was preparing a manuscript for...Ch. 17 - a. Why is the pKa of the glutamate side chain...Ch. 17 - Prob. 38PCh. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 40PCh. 17 - Prob. 41PCh. 17 - Three peptides were obtained from a trypsin...Ch. 17 - Prob. 43PCh. 17 - After the polypeptide shown here was treated with...Ch. 17 - The disulfide bridges of a polypeptide were...Ch. 17 - -Amino acids can be prepared by treating an...Ch. 17 - Reaction of a polypeptide with carboxypeptidase A...Ch. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Show how valine can be prepared by a. a Strecker...Ch. 17 - Prob. 51PCh. 17 - Why is proline never found in an -helix?Ch. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 55PCh. 17 - A chemist wanted to test his hypothesis that the...Ch. 17 - A normal polypeptide and a mutant of the...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider the Grignard reaction below to answer the following questions. A Mgar 1. ether + MyC CH3 2H3O C B a. The electrophile in this reaction is: b. The nucleophile in this reaction is: c. The alcohol product can be classified as a: a. 1° alcohol b. 2° alcohol C. 3° alcohol d. 4° alcohol HO CH3 CHarrow_forwardGive the major organic product(s) for each of the following reactions or sequences of reactions. Show all relevant stereochemistry A. CH₂OH PCC CH2Cl2 HOO B. H KCN HCN of b C. 1. CH,MgBr, ether 2 HO* D. Choose the BEST reagent for carrying out each of the following conversions. CO₂CH3 CO₂CH3 OH CO₂H сон ن نے a. LiAlH4, ether at abinayo iss c b. NaBH4, ethanol C. CrO3, pyridine d. H₂/Pd d notsiolarrow_forwardChoose the best reagent for carrying out the following reactions from the list below. Place the letter of the reagent(s) in the box over the reaction arrow. Use only one letter per box. OH OH CH CH CH3 CHS CH3 f OH OCH 3 H A. NaH, then CHI B. C. m-ClC6H4COзH D. E. warm H2SO4/H₂O F. G. H₂/Pd H. I. Cl₂, H₂O J. NaOCH3, CH3OH CH3MgBr in ether, then H3O+ Hg(O2CCF3)2, CH3OH PCC, CH2Cl2 LiAlH4 in ether, then H3O+arrow_forward
- What is the product of the reaction of 2,4-pentanedione with phenylhydrazine?arrow_forwardIn the reaction of naphthalene with CrO3 in acetic acid. Indicate whether a different product is obtained if carried out at 25°C or with heating (A).arrow_forwardQUESTION: Fill in the answers in the empty green boxes 1. Step 2 2. Step 3 3. Step 4 (SUM) 4. Step 5 (df) (GIVEN) 5. Determine S y/x value *The data values have been provided in the worksheet attached in the first image*arrow_forward
- If the symbol A is placed in a reaction, at what temperature does it take place?arrow_forwardBy malonic or acetylacetic synthesis, synthesize 3-methyl-4-oxopentanoic acid (indicate the formulas of the compounds).arrow_forwardoalmitic acid is a 16 carbon acid. In a balanced equation, the products of the sponification of tripalmitin (glyceryl tripalmitate are blank.arrow_forward
- Write the esterification reaction mechanism of salicylic acid and acetic acid to produce aspirin (acetylsalicylic acid). Note: salicylic acid will act as the alcoholarrow_forwardWhat type of interaction would you expect between the following R groups in the tertiary structure of a protein? O -CH2-CO and -CH2-CH2-CH2-CH2-NH3+ a. disulfide bonds b. salt bridges c. hydrogen bonds HO abios vist anisinoo tedt bigil s ai loistaslor sale! 10 OUT d. hydrophobic interactions e. peptide bondsarrow_forward4. True or false: This skeletal structure represents a saturated fatty acid. Ini to 0 fale) me OH faistong starrow_forward
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