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Chapter 12: Q 14 P (page 385)

Question: Propose structures for compounds that fit the following mass-spectral data:

(a) A hydrocarbon with M+=132

(b) A hydrocarbon with M+=166

(c) A hydrocarbon with M+=84

Short Answer

Expert verified

Possible structures of molecule:

a)

C10H12

b)

C12H22

c)

C6H12

Step by step solution

01

Molecular mass

Molecular mass of a substance is the sum of atomic masses of all its atoms in a molecule.

02

Calculation of molecular formula

  • These molecules have only hydrogen and carbon.

  • Molecular mass of carbon is 12 and molecular mass of hydrogen is 1.

  • Sum of molecular mass of C and H is12+1=13

  • Now divide the given molecular mass by 13.

  • The quotient indicates the number of carbon and number of hydrogen is equal to the quotient plus the remainder.

03

Molecular formula of given molecules

(a) A hydrocarbon with molecular weight 132:

  • Given by: 13213=10213

  • This indicates that there are 10 carbon and 12 hydrogens.

  • So, the formula isC10H12




(b) A hydrocarbon with molecular weight 166:

  • Given by: 16613=121013

  • This indicates that there are 12 carbon and 22 hydrogen.

  • So, the formula is C12H22




Here one more structure is possible with formula C13H10.

(c) A hydrocarbon with molecular weight 84:

  • Given by: 8413=6613

  • This indicates that there are 10 carbon and 12 hydrogen.

  • So, the formula isC6H12




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Most popular questions from this chapter

Question: 4-Methyl-2-pentanone and 3-methylpentanal are isomers. Explain how you could tell them apart, both by mass spectrometry and by infrared spectroscopy.

Question: How could you use infrared spectroscopy to distinguish between the

following pairs of isomers?

(a)HC≡CCH2NH2andCH3CH2C≡N

(b)CH3COCH3andCH3CH2CHO

Draw and name the following

a) The eight carboxylic acids with the formula C6H12O2

b) Three nitriles with the formula C5H7N

Predict the product(s) and provide the mechanism for each reaction below. What does each mechanism have in common?

b.

c.

d.

Question:The mass spectrum (a) and the infrared spectrum (b) of an unknown hydrocarbon are shown. Propose as many structures as you can.
See all solutions

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