To draw: The reactions that took place and the product formed. Interpretation: The reactions that took place are to be drawn and the product formed is to be shown. Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula. Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

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Answer 1

Question

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

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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

Answer 2

Question

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

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Answer 3

Question

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

Expert Solution & Answer

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Answer 4

Question

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

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Answer 5

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

Answer 6

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

Answer 7

Chapter 12, Problem 12.26SP

(a)

Interpretation Introduction

To draw: The reactions that took place and the product formed.

Interpretation: The reactions that took place are to be drawn and the product formed is to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecular formula.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

Answer 8

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

Answer 9

(b)

Interpretation Introduction

To determine: Whether the molecular ion is or is not visible in the mass spectrum and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101.

Interpretation: Whether the molecular ion is or is not visible in the mass spectrum is to be explained and the ions which are likely to be responsible for the strong peaks at m/z 59 and 101 are to be shown.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak with having an even mass number corresponding to the loss of an even mass number.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6P Ch. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...

Solution Summary: The author explains that mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives information about the molecule. Fragmentation gives resonance stabilized cations whenever possible.

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Chapter 12 Solutions