
Concept explainers
Interpretation:
The retrosynthesis analysis and the actual synthesis are to be written for the preparation of each target molecule from the given starting molecule.
Concept introduction:
>The retrosynthesis is a reaction that involves
on acid catalyzed dehydration, an alcohol gives the corresponding more substituted alkene as the major product.
>The alkene, on reaction with halogen in water, undergoes addition of halogen and hydroxyl group across the double bond in a way that the halogen atom is bonded to the less substituted double bonded carbon atom and hydroxyl group is bonded to the more substituted double bonded carbon atom.
>Alkenes react with hydrogen halide and yield haloalkane.
>Alkenes, on hydration, form more substituted alcohol.
>Alkenes, on hydroboration-oxidation, form less substituted alcohol.
>Alkenes, in presence of peroxy acid, undergo
In presence of a strong base,

Answer to Problem 50P
Solution:
The retrosynthetic analysis and the actual synthesis for the preparation of each target molecule from the given starting compound are as follows:
a)
Retrosynthesis:
Synthesis:
b)
Retrosynthesis:
Synthesis:
c)
Retrosynthesis:
Synthesis:
d)
Retrosynthesis:
Synthesis:
e)
Retrosynthesis:
Synthesis:
f)
Retrosynthesis:
Synthesis:
g)
Retrosynthesis:
Synthesis:
h)
Retrosynthesis:
Synthesis:
Explanation of Solution
a)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
b)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
c)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
d)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
e)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
f)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
g)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
h)
Retrosynthetic analysis for the target molecule
The actual synthetic route for the above retrosynthesis is as follows:
Therefore, the retrosynthesis and synthesis reactions for the given compounds were proposed.
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Chapter 8 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
- For this question, if the product is racemic, input both enantiomers in the same Marvin editor. A) Input the number that corresponds to the reagent which when added to (E)-but-2-ene will result in a racemic product. Input 1 for Cl, in the cold and dark Input 2 for Oy followed by H₂O, Zn Input 3 for D₂ with metal catalyst Input 4 for H₂ with metal catalyst B) Draw the skeletal structure of the major organic product made from the reagent in part A Marvin JS Help Edit drawing C) Draw the skeletal structure of the major organic product formed when (2)-but-2-ene is treated with peroxyacetic acid. Marvin 35 Helparrow_forwardMichael Reactions 19.52 Draw the products from the following Michael addition reactions. 1. H&C CH (a) i 2. H₂O* (b) OEt (c) EtO H₂NEt (d) ΕΙΟ + 1. NaOEt 2. H₂O' H H 1. NaOEt 2. H₂O*arrow_forwardRank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic. НОН НЬ OHd Онсarrow_forward
- Can the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left? ? starting material target If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area. Be sure you follow the standard ALEKS rules for submitting syntheses. + More... Note for advanced students: you may assume that you are using a large excess of benzene as your starting material. C :0 T Add/Remove step Garrow_forwardThe following equations represent the formation of compound MX. What is the AH for the electron affinity of X (g)? X₂ (g) → 2X (g) M (s) → M (g) M (g) M (g) + e- AH = 60 kJ/mol AH = 22 kJ/mol X (g) + e-X (g) M* (g) +X (g) → MX (s) AH = 118 kJ/mol AH = ? AH = -190 kJ/mol AH = -100 kJ/mol a) -80 kJ b) -30 kJ c) -20 kJ d) 20 kJ e) 156 kJarrow_forwardA covalent bond is the result of the a) b) c) d) e) overlap of two half-filled s orbitals overlap of a half-filled s orbital and a half-filled p orbital overlap of two half-filled p orbitals along their axes parallel overlap of two half-filled parallel p orbitals all of the abovearrow_forward
- Can the target compound at right be efficiently synthesized in good yield from the unsubstituted benzene at left? starting material target If so, draw a synthesis below. If no synthesis using reagents ALEKS recognizes is possible, check the box under the drawing area. Be sure you follow the standard ALEKS rules for submitting syntheses. + More... Note for advanced students: you may assume that you are using a large excess of benzene as your starting material. C T Add/Remove step X ноarrow_forwardWhich one of the following atoms should have the largest electron affinity? a) b) c) d) 으으 e) 1s² 2s² 2p6 3s¹ 1s² 2s² 2p5 1s² 2s² 2p 3s² 3p² 1s² 2s 2p 3s² 3p6 4s2 3ds 1s² 2s² 2p6arrow_forwardAll of the following are allowed energy levels except _. a) 3f b) 1s c) 3d d) 5p e) 6sarrow_forward
- A student wants to make the following product in good yield from a single transformation step, starting from benzene. Add any organic reagents the student is missing on the left-hand side of the arrow, and any addition reagents that are necessary above or below the arrow. If this product can't be made in good yield with a single transformation step, check the box below the drawing area. Note for advanced students: you may assume that an excess of benzene is used as part of the reaction conditions. : ☐ + I X This product can't be made in a single transformation step.arrow_forwardPredict the major products of this organic reaction:arrow_forwardCalculate the density of 21.12 g of an object that displaces 0.0250 L of water.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning

