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CHM 219 Module 5 Exam Questions & Answers.
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CHM 219 Module 5 Exam Questions & Answers.
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CHM 219 Module 5 Exam Questions &Answers
Alcohol j- jANS-Generic jformula jR-OH, jdefined jby jthe jpresence jof ja jHydroxyl jgroup j(-
OH). jOrganic jderivatives jof jwater, jas jone jof jthe jhydrogen jatoms jfrom jthe jwater
jmolecule jis jreplaced jby jan jalkyl jgroup.
Phenols j- jANS-Hydroxyl jgroup jdirectly jattached jto ja jbenzene jring
Methyl jAlcohol j- jANS-Only jH jatoms jattached jto jthe jcarbon jbearing jthe-OH jgroup
Primary jAlcohol j- jANS-one jalkyl jgroup jattached jto jthe jcarbon jatom jbonded jto jthe j-
OH jgroup
Secondary jAlcohol j- jANS-Two jalkyl jgroups jattached jto jthe jcarbon jatom jbonded jto jthe
j-OH jgroup
Tertiary jAlcohol j- jANS-Three jalkyl jgroups jattached jto jthe jcarbon jatom jbonded jto jthe j-
OH jgroup
Boiling jPoint jof jAlcohols j- jANS-High jdue jto jHydrogen jbonding jbetween jthe jpositively
jcharged jH jand jnegatively jcharged jO
Water jsolubility jof jalcohols j- jANS-As jthe jcarbon jchain jlength jincreases jalcohol
jbecomes jcorrespondingly jless jsoluble jin jwater.
Alcohols jAcidity/Basicity j- jANS-Can jact jas ja jweak jbase j(accepting jH+ jusing ja jlone
jpair jon jthe jO jatom) jor jweak jacid j(donating jthe jO-H jproton jas jH+)
Amphoteric j- jANS-a jsubstance jthat jcan jact jas jboth jan jacid jand ja jbase
Alkoxide jIon j- jANS-conjugate jbase jof jan jalcohol, jvery jstrong jbase
Alkyloxonium jIon j- jANS-The jconjugate jacid jof jthe jalcohol jis joften jcalled ja jprotonated
jalcohol,
Dehydration j- jANS-Loss jof jwater. jAn jalcohol jmolecule jwill jlose jH2O jto jform jan
jALKENE. jType jof jelimination jreaction j— jlose jthe j-OH jfrom jone jC jand jH jatom jfrom
jthe jadjacent jC. j
First jstep j— jalcohol jacts jas ja jbase. j
Tertiary jalcohols j- jE1
, Primary jalcohols j- jE2
All jdehydration jbegins jwith... j- jANS-Protonation jof jthe jalcohol jgroup.
Order jof jease jof jdehydration jof jalcohol jsubstrates... j- jANS-3>2>1
jTertiary jrequire jthe jleast jharsh jconditions j(typically j25% jaqueous jacid jand j60-80
jdegrees jC) jwhereas jprimary jrequire jfully jconcentrated jacid jand jtemperatures
japproaching j200 jdegrees jC.
If jmore jthan jone jalkene jproduct jis jpossible... j- jANS-The jmajor jproduct jis jthe jone
jwhose jC=C jhas jmore jalkyl jgroups jattached.
ZAitsev's jRule j- jANS-The jproduction jof jthe jmore jhighly jsubstituted jalkene jas jthe
jmajor jproduct.
Alcohols j—> jAlkyl jHalides j- jANS--Substitution jREaction j, jreplacing jthe j-OH jwith ja
jhalogen
-Alcohol j(R-OH) j+ jHydrogen jHalide j(H-X) j——> jalkyl jhalide j(R-X) j+ jwater j(H-OH)
-the juse jof jHydrogen jhalides jpromotes jthe jsubstitution jin jtwo jways j
1. jAcid jprotonates jthe j-OH jof jthe jalcohol jto jmake jit ja jgood jleaving jgroup
2. jHalide jions jare jgood jnucleophiles jbut jweak jbases jso jsubstitution jis jpromoted jover
jelimination
Order jof jReactivity jof jAlcohols jwith jHX j- jANS-3>2>1
Primary jAlcohols jreact jvia.... j(With jHX) j- jANS-Sn2
-OH jgroup jis jprotonated jand jthen jdisplaced jas ja jwater jmolecule jby ja jchloride jion
Secondary jAlcohols jreact jvia... j(with jHX) j- jANS-Sn1 jor jSn2 j- jdepending jon jthe
jstructure jof jthe jspecific jalcohol
Conversion jusing jPhosphorous jHalides j(PX3) j- jANS-X= jCl jor jBr
- jAlcohol j(3R-OH) j+ jphosphorous jtrihalide j(X2P-X) j—> jalkyl jhalide j(3R-X) j+ jH3PO3
-particularly jefficient jas jone jmolecule jof jPX3 jcan jconvert j3 jmolecules jof jalcohol jto jthe
jcorresponding jalkyl jhalide j
-byproduct jof jthe jreaction jis jphosphorous jacid
Conversion jusing jThionyl jChloride j(SOCl2) j- jANS-Alcohol j(R-OH) j+ jThionyl jChloride
j(Cl-S=O-Cl) j—> jalkyl jChloride j(R-Cl) j+ jSO2 j^ j+ jHCl
- jvery jefficient jwith jprimary jand jsecondary jalcohols jd/t jthe jmain jbyproduct j(SO2) jbeig
jformed jas ja jgas jand jleaving jthe jreaction jmixture.
Oxidation jto jAldehydes, jKetones jand jCArboxylic jAcids j- jANS-Oxidation j- jincreasing
jthe joxygen jcontent j(number jof joxygen jatoms) jor jthe joxygen jcharacter j(more jbonds
jto joxygen)
-Primary jAlcohols j—> jaldehydes j—> jCarboxylic jAcids
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