Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter F, Problem F.17P
Interpretation Introduction

(a)

Interpretation:

The structure of pentanoyl chloride is to be drawn.

Concept introduction:

The structure of a compound can be drawn on the basis of its IUPAC name. The IUPAC name is made of three parts, prefix, root, and suffix. The suffix indicates the highest priority group present. Its location is written as a prefix for the functional group name unless redundant. The root is the longest continuous carbon chain that also includes the highest priority functional group. Any other functional groups present are listed alphabetically as prefixes along with their locants.

If any chiral carbons are present, their absolute configurations are specified at the start along with the carbon number if necessary. Similarly, the stereochemistry (E/Z) of any double bond is also specified at the start. A di, tri, etc., before a prefix or suffix, indicates the number of instances of that functional group.

Interpretation Introduction

(b)

Interpretation:

The structure of 4-(2-methylpropyl)heptanedioyl chloride is to be drawn.

Concept introduction:

The structure of a compound can be drawn on the basis of its IUPAC name. The IUPAC name is made of three parts, prefix, root, and suffix. The suffix indicates the highest priority group present. Its location is written as a prefix for the functional group name unless redundant. The root is the longest continuous carbon chain that also includes the highest priority functional group. Any other functional groups present are listed alphabetically as prefixes along with their locants.

If any chiral carbons are present, their absolute configurations are specified at the start along with the carbon number if necessary. Similarly, the stereochemistry (E/Z) of any double bond is also specified at the start. A di, tri, etc., before a prefix or suffix, indicates the number of instances of that functional group.

Interpretation Introduction

(c)

Interpretation:

The structure of (S)-5-phenyloctanoyl chloride is to be drawn.

Concept introduction:

The structure of a compound can be drawn on the basis of its IUPAC name. The IUPAC name is made of three parts, prefix, root, and suffix. The suffix indicates the highest priority group present. Its location is written as a prefix for the functional group name unless redundant. The root is the longest continuous carbon chain that also includes the highest priority functional group. Any other functional groups present are listed alphabetically as prefixes along with their locants.

If any chiral carbons are present, their absolute configurations are specified at the start along with the carbon number if necessary. Similarly, the stereochemistry (E/Z) of any double bond is also specified at the start. A di, tri, etc., before a prefix or suffix, indicates the number of instances of that functional group.

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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.
Give the product of the bimolecular elimination from each of the isomeric halogenated compounds. Reaction A Reaction B. КОВ CH₂ HotBu +B+ ко HOIBU +Br+ Templates More QQQ Select Cv Templates More Cras QQQ One of these compounds undergoes elimination 50x faster than the other. Which one and why? Reaction A because the conformation needed for elimination places the phenyl groups and to each other Reaction A because the conformation needed for elimination places the phenyl groups gauche to each other. ◇ Reaction B because the conformation needed for elimination places the phenyl groups gach to each other. Reaction B because the conformation needed for elimination places the phenyl groups anti to each other.
Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane The IR spectra of these five alkenes have the key absorptions (in cm Compound Compound A –912. (§), 994 (5), 1643 (%), 3077 (1) Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption) Compound C Compound D) –714 (5), 1665 (w), 3010 (m) 885 (3), 1650 (m), 3086 (m) 967 (5), no aharption 1600 to 1700, 3040 (m) Compound K Match each compound to the data presented. Compound A Compound B Compound C Compound D Compound
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