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Compound X, isolated from lanolin (sheep’s wool fat), has

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 33SP Chapter 1

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 33SP

Compound X, isolated from lanolin (sheep’s wool fat), has the pungent aroma of dirty sweatsocks. A careful analysis showed that compound X contains 62.0% carbon and 10.4% hydrogen. No nitrogen or halogen was found.

(a) Compute an empirical formula for compound X.

(b) A molecular weight determination showed that compound X has a molecular weight of approximately 117. Find the molecular formula of compound X.

(c) Many possible structures have this molecular formula. Draw complete structural formulas for four of them.

Step-by-Step Solution:

Answer :

Step 1</p>

(a) To write an empirical formula of the compound X.

62% means 62 gram carbon; 10.4 gram hydrogen;.

1. find the mole of each element:

mole C 62 g/12.01=5.17 mol

mole H 10.4/1.008=10.31 mol .

2. Divided each by the smallest number; 5.17mol is the smallest number from above to get our subscript.

C: 5.17/5.17=1

H: 10.31/5.17=2

The molecular formula of compound X is( CH2)

(b) A molecular weight determination showed that compound X has a molecular weight of approximately 117. Find the molecular formula of compound X.

The molecular formula of compound X we got is CH2 and molecular weight is 14 ,

                                       =117/14.

                                       =8.3

The molecular formula of the compound is (CH2)*8=C8H16.

(C) Many possible structures have this molecular formula. Draw complete structural formulas for four of them.

Possible structures of cyclo octane :

1)cis -2 octene

2)Z-2-octene

Step 2 of 3

Chapter 1, Problem 33SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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