EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
Question
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Chapter 4, Problem 51PP

(a)

Interpretation Introduction

Interpretation:

Chair conformations of given compound should be drawn and most stable conformer is needed to be predicted between them.

Concept introduction:

Chair conformer: chair conformer is a stable conformer for cyclohexane compound. In this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.

Example:

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 4, Problem 51PP , additional homework tip  1

After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.

Stereochemistry conversions in chair conformation are shown below.

Substituent position cis trans
1,2 position (a,e) or (e,a) (a,a) or (e,e)
1,3 position (a,a) or (e,e) (a,e) or (e,a)
1,4 position (a,e) or (e,a) (a,a) or (e,e)

(b)

Interpretation Introduction

Interpretation:

Chair conformations of given compound should be drawn and most stable conformer is needed to be predicted between them.

Concept introduction:

Chair conformer: chair conformer is a stable conformer for cyclohexane compound. In this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.

Example:

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 4, Problem 51PP , additional homework tip  2

After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.

Stereochemistry conversions in chair conformation are shown below.

Substituent position cis trans
1,2 position (a,e) or (e,a) (a,a) or (e,e)
1,3 position (a,a) or (e,e) (a,e) or (e,a)
1,4 position (a,e) or (e,a) (a,a) or (e,e)

(c)

Interpretation Introduction

Interpretation:

Chair conformations of given compound should be drawn and most stable conformer is needed to be predicted between them.

Concept introduction:

Chair conformer: chair conformer is a stable conformer for cyclohexane compound. In this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.

Example:

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 4, Problem 51PP , additional homework tip  3

After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.

Stereochemistry conversions in chair conformation are shown below.

Substituent position cis trans
1,2 position (a,e) or (e,a) (a,a) or (e,e)
1,3 position (a,a) or (e,e) (a,e) or (e,a)
1,4 position (a,e) or (e,a) (a,a) or (e,e)

(d)

Interpretation Introduction

Interpretation:

Chair conformations of given compound should be drawn and most stable conformer is needed to be predicted between them.

Concept introduction:

Chair conformer: chair conformer is a stable conformer for cyclohexane compound. In this chair conformer two positions are important for substitutions one is equatorial and other one axial position. Axial positions are parallel to the axis of ring while equatorial positions are perpendicular to the axis of the ring.

Example:

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, Chapter 4, Problem 51PP , additional homework tip  4

After ring flip of the conformer, axial position becomes equatorial and equatorial position becomes axial.

Stereochemistry conversions in chair conformation are shown below.

Substituent position cis trans
1,2 position (a,e) or (e,a) (a,a) or (e,e)
1,3 position (a,a) or (e,e) (a,e) or (e,a)
1,4 position (a,e) or (e,a) (a,a) or (e,e)

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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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