HowtoCalculateDBE

Hellofriends!HaveproblemswithcalculatingDBE?Noworries!Hereisthetutorialwhichwill
helpyoustepbystep.Hopefullyafterreadingthistutorial,youcancalculateDBEfasterand
moreaccurately.

WhatisDBE?
DBE=doublebondequivalent.Itisalsocalleddegreeofunsaturation.Fromthestructureofthe
chemicals,eachpibondorringwillgenerateoneDBE.

Forexample:
1. Ethylene,C2H6,isasaturatedacyclicalkaneanditdoesnothaveanypibondor
ring,soDBE=0.
2.Propylene,C3H6,containsapibond,soDBE=1.
3.Cyclohexane,C6H12,containsaring,soDBE=1.

Ethylene.Propylene.Cyclohexane
DBE=0DBE=1DBE=1

Thechemicalformulaandthechemicalstructurearehighlyrelated:eachpibondorringwill
causeapairofHlessthanthemaximumnumber.Therefore,forhydrocarbon,eachpairofH
lessthanmaxHcount,whichisequaltothesaturatedacyclicalkane,iscountforoneDBE.
Thinkquestion:HowmanyDBEisinC2H5Cl?
WhyweneedtoknowDBE?

Infraredspectroscopyisveryusefultooltoanalyzethestructureofanunknownchemical.
CalculatingDBEisanimportantstepbeforeanalyzingthefunctionalgroupsanditwillofferus
morecluestonarrowdowntheoptionsoffunctiongroupsandmaketheworkeasier.
HowtocalculatetheDBEifwedonotknowthestructureofthechemicals?

ForChem14C,alltheproblemswehaveevermettalkabouttheorganicchemicalswhichonly
containcarbon,oxygen,hydrogen,nitrogen,andhalogens.Therefore,peoplesummarizeda
DBEformulaforourconvenience.

Inthisformula,Cmeansthenumberofcarbon.Hmeansthenumberofhydrogenandhalogen.
Nmeansthenumberofthenitrogen.

Letsapplytheformulatothechemicalsthatwementionedbefore.
Ethylene(C2H6):DBE=C(H/2)+(N/2)+1=2(6/2)+(0/2)+1=0
Propylene(C3H6):DBE=C(H/2)+(N/2)+1=3(6/2)+(0/2)+1=1
Cyclohexane(C6H12):DBE=C(H/2)+(N/2)+1=6(12/2)+(0/2)+1=1

Thinkquestion:Howdidpeoplegetthisformula?

OtherimportantthingsyouneedtoknowaboutDBE:
1.DBEisanonnegativeinteger.IfyougotanegativeorafractionDBE,youwillhavetogo
backandcheckyourmathmistake!
2.MemorizethefollowingfactsanditwillbemoreconvenientwhenyouapplyDBEto
figureoutthechemicalstructure:
DoublebondcontainsoneDBE.
TriplebondcontainstwoDBE.
AbenzeneringcontainsfourDBE.
3.DoNOTdoublecounttheringsinthechemicalstructure.
E.g.

Onlycounttworingsinthisstructure
5pibonds+2rings=>DBE=5+2=7

Beforewestartthepracticeproblem,letmeexplainthethinkquestionsfirst:
Question1:HowmanyDBEisinC2H5Cl?
Inthiscase,C2H5Clisnothydrocarbon,sowecannotsimplytelltheDBEfromhowmuchH
doesitlack.However,halogensusuallyformonesinglebondtowithotheratoms,whichisthe
sameashydrogen.WecanimaginethatthestructureofC2H5ClissimilartoC2H6,inwhichcase
DBE=0.
Question2:Howdowegetthisformula?
AccordingtotheHydrogen/HalogenRule,maxnumberofhydrogens+halogens=2C+N+2.We
discussedthateachpairofhydrogenandhalogenslessthanmaxhydrogensandhalogenscount
equalsDBE.

Practiceproblem
1. LookatthechemicalstructurebelowandcalculatetheDBE.

1)

2)

4)

5)

3)

6)

2.UsetheformulatocalculatetheirDBE.
1)C8H102)C6H12O63)C3H4Cl2
4)C8H7N5)C13H106)C4H9NO

Answerkeyforthepracticeproblems:
1. 1)Onepibond.DBE=1
2)Twopibonds.DBE=2
3)Onepibond.DBE=1
4)Tworings.DBE=2
5)Onepibondsandthreerings.DBE=4
6)Threepibondsandoneringinthemiddleandthreepibondsonsubstituents.DBE=7
2.1)DBE=C(H/2)+(N/2)+1=8(10/2)+(0/2)+1=4
2)DBE=C(H/2)+(N/2)+1=6(12/2)+(0/2)+1=1
3)DBE=C(H/2)+(N/2)+1=3(6/2)+(0/2)+1=1
4)DBE=C(H/2)+(N/2)+1=8(7/2)+(1/2)+1=6
5)DBE=C(H/2)+(N/2)+1=13(10/2)+(0/2)+1=9
6)DBE=C(H/2)+(N/2)+1=4(9/2)+(1/2)+1=1

Reference:
Hardinger, Steven. Chemistry 14C: Structure of Organic Molecules : Course Thinkbook : Concept Focus
Questions, OWLS Problems, Practice Problems. Plymouth, MI: Hayden-McNeil, 2011. Print.
Hardinger, Steven. Chemistry 14C: Organic Molecular Structures and Interactions : Lecture
Supplements. Plymouth, MI: Hayden-McNeil Pub., 2008. Print.