Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 2, Problem 3CTQ
Interpretation Introduction
Interpretation : A shell representation and Lewis structure for ion of fluorine that is most likely to be stable should be drawn.
Concept Introduction : A legitimate Lewis structure is an electron dot and line bond representation in which the total number of valence electrons is indicated. Number of valence electrons around hydrogen is two. Number of valence electrons around carbon, nitrogen, oxygen, fluorine atom is eight. This is called the octet rule.
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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
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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 2 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 2 - Prob. 1CTQCh. 2 - The valence shell of an atom in a legitimate Lewis...Ch. 2 - Prob. 3CTQCh. 2 - Prob. 4CTQCh. 2 - Prob. 5CTQCh. 2 - It is impossible to draw a legitimate Lewis...Ch. 2 - Describe how to calculate the total number of...Ch. 2 - Prob. 8CTQCh. 2 - Prob. 9CTQCh. 2 - Prob. 10CTQ
Ch. 2 - Prob. 11CTQCh. 2 - Prob. 12CTQCh. 2 - A complete Lewis structure must show all nonzero...Ch. 2 - Prob. 14CTQCh. 2 - Prob. 15CTQCh. 2 - Prob. 16CTQCh. 2 - Prob. 17CTQCh. 2 - Prob. 18CTQCh. 2 - Complete the rest of the table for N, O or X by...Ch. 2 - Prob. 20CTQCh. 2 - Prob. 21CTQCh. 2 - Make a checklist that can be used to determine if...Ch. 2 - Prob. 2ECh. 2 - Prob. 3ECh. 2 - Draw the Lewis structure of a neutral molecule...Ch. 2 - Prob. 5ECh. 2 - For each element, predict (and draw a Lewis...Ch. 2 - Predict which of the following species is least...Ch. 2 - The molecules BH3 and SF6 and the ion SO42 exist...Ch. 2 - These are NOTlegitimate Lewisstructures (and...Ch. 2 - Fill in missing formal charges where needed (all...Ch. 2 - Below each structure in the previous question is a...Ch. 2 - Prob. 12ECh. 2 - Carbon monoxide (CO) is an example of an overall...Ch. 2 - Explain why this Lewis structure for CO is not as...Ch. 2 - Prob. 15ECh. 2 - Prob. 16ECh. 2 - Prob. 17ECh. 2 - Prob. 18ECh. 2 - Prob. 19E
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