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Chapter 13: Q 26. (page 521)

Question:Which compound gives a molecular ion at m/z= 122:C6H5CH2CH2CH3 , C6H5COCH2CH3 , or C6H5OCH2CH3?

Short Answer

Expert verified

Answer

C8H10O, Molecular ion peak atm/z = 122

Step by step solution

01

Mass Spectra

The spectroscopic technique used for the identification of a compound based on the mass of the compound is referred to as mass spectroscopy. The spectra obtained from this spectroscopy are referred to as mass spectra.

02

Structure determination

In mass spectroscopy, the structure is determined on the basis of the mass of the given structure

C9H12 , Molecular ion peak at m/z = 120

C9H10O , Molecular ion peak at m/z = 134

C8H10O , Molecular ion peak at m/z = 122

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Most popular questions from this chapter

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1.

a. Identify the structures of A and B.

b. Draw a mechanism for the conversion of citronellol to isopulegone.

c. Draw a mechanism for the conversion of isopulegone to B.

Question:Like alcohols, ethers undergo 伪 cleavage by breaking a carbon鈥揷arbon bond between an alkyl group and the carbon bonded to the ether oxygen atom; that is, the red C鈥揅 bond in R鈥�CH2OR'is broken. With this in mind, propose structures for the fragments formed by 伪 cleavage of(CH3)2CHCH2OCH2CH3. Suggest a reason why an ether fragments by 伪 cleavage.

Question:Suppose you have two bottles, labeled ketone A and ketone B. You know that one bottle contains CH3CO(CH2)5CH3and one contains CH3CH2CO(CH2)4CH3but you do not know which ketone is in which bottle. Ketone A gives a fragment at m/z= 99 and ketone B givesa fragment at m/z= 113. What are the likely structures of ketones A and B from these fragmentation data?

Question: Which of the following has higher energy:

(a) IR light of 3000 cm鈭�1or 1500 cm鈭�1in wavenumber;

(b) IR light having a wavelength of 10 碌m or 20 碌m?

Question:For each compound, assign likely structures to the fragments at each m/zvalue, and explain how each fragment is formed.

a. : peaks at m/z= 104, 91

b. : peaks at m/z= 71, 68, 41, 31
See all solutions

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