ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY.
4th Edition
ISBN: 9781119832638
Author: Klein
Publisher: WILEY
Question
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Chapter 15, Problem 32PP

 (a)

Interpretation Introduction

Interpretation: For the given molecular formulae the structure should be predicted.

Concept Introduction:

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

HDI (Index of hydrogen deficiency): HDI values gives information on the level of unsaturation (means a double bond or a ring) on the structure of the compound.

 HDI=( 2C+2+N-H-X) 2WhereNumberofcarbonatomsisCNumberofnitrogenatomsisNNumberofhydrogenatomsisHNumberofhalogenatomsisX

 (a)

Expert Solution
Check Mark

Answer to Problem 32PP

Answer

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY., Chapter 15, Problem 32PP , additional homework tip  1

Explanation of Solution

To predict: the structure for the given molecular formula. C5H10

Calculate HDI Value for the given molecular formula and draw the structure.

C5H10:HDI=2(5)+2102=22=1

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY., Chapter 15, Problem 32PP , additional homework tip  2

HDI = 1, compound has either 1 ring or one π -bond. If it is the unsaturated compound, it will give more than one signal thus it is wrong. In the saturated ring, all the protons are chemically equivalent through either axis of symmetry or plane of symmetry gives only one signal in the spectrum.

Therefore, the compound predicted is the cyclopentane.

(b)

Interpretation Introduction

Interpretation: For the given molecular formulae the structure should be predicted.

Concept Introduction:

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

HDI (Index of hydrogen deficiency): HDI values gives information on the level of unsaturation (means a double bond or a ring) on the structure of the compound.

 HDI=( 2C+2+N-H-X) 2WhereNumberofcarbonatomsisCNumberofnitrogenatomsisNNumberofhydrogenatomsisHNumberofhalogenatomsisX

(b)

Expert Solution
Check Mark

Answer to Problem 32PP

Answer

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY., Chapter 15, Problem 32PP , additional homework tip  3

Explanation of Solution

The structure of given molecular formula.( C5H8Cl4 )

Calculate HDI value for the given molecular formula and draw the structure:

C5H8Cl4:HDI=2(5)+2842=0

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY., Chapter 15, Problem 32PP , additional homework tip  4

HDI = 0 , tells the compound is fully saturated (no double bond, triple bond or rings) and the compound is acyclic. Only one proton signal indicates all 4-  CH2 protons bonded to the same carbon possess high degree of symmetry.

Therefore the predicted compound is 1, 3-dichoro-2, 2-dimethylchloropropane.

 (c)

Interpretation Introduction

Interpretation: For the given molecular formulae the structure should be predicted.

Concept Introduction:

1H NMR: A technique gives information to predict the Carbon and Hydrogen connectivity in the organic compounds.

HDI (Index of hydrogen deficiency): HDI values gives information on the level of unsaturation (means a double bond or a ring) on the structure of the compound.

 HDI=( 2C+2+N-H-X) 2WhereNumberofcarbonatomsisCNumberofnitrogenatomsisNNumberofhydrogenatomsisHNumberofhalogenatomsisX

 (c)

Expert Solution
Check Mark

Answer to Problem 32PP

Answer

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY., Chapter 15, Problem 32PP , additional homework tip  5

Explanation of Solution

To find:  the structure of given molecular formula. C12H18

Calculate HDI value for the given molecular formula and draw the  structure:

C12H18:HDI=2(12)+2182=82=4

ORG.CHEM.WILEYPLUSNEXTGEN.W/LLTEXT+STDY., Chapter 15, Problem 32PP , additional homework tip  6

HDI = 4, shows the compound is aromatic ring (having 3 double bonds and 1 ring) having each methyl group (- CH3 group) attached to carbon of the aromatic ring. All the eighteen protons are chemically equivalent through either axis of symmetry or plane of symmetry possessing high degree of symmetry.

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