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CHEM211 Problem SetFunctional Groups and Reaction TypesThese answers are only suggestions. You will likely have very different structures.Draw molecules with the following functional groups:1. cyclic alkene, quaternary carbonDraw the product of an ADDITION reaction of your molecule with H2(H-H).2. alkane, tertiary chlorideDraw the product of a SUBSTITUTION reaction of your molecule with NaI (NaCl is the other product).
Cl
I
3. acyclic terminal alkeneDraw the product of a REARRANGEMENT reaction of your molecule to form an isomeric alkene.4. allylic secondary alcoholDraw the product of an ELIMINATION reaction of your molecule in which H2O is eliminated.
OH
5. ketone, aryl amineDraw the product of an ADDITION reaction of theketone double bond in your molecule with H2.
OH
2
NOHH
2
N
6. primary benzylic bromideDraw the product of a SUBSTITUTION reaction of your molecule with KOH (KBr is the other product).
Br OH
7. cyclic alkene, aldehydeDraw the product of an ADDITION the carbon-carbondouble bond with Br 2(Br-Br).
HOHOBr Br 
8. cyclic alkane, tertiary bromideDraw a product of an ELIMINATION reaction of your molecule in which H-Br is eliminated.
Br 
 
9. secondary iodide, aryl etherDraw the product of a SUBSTITUTION reaction of your molecule’s I with NaSH (NaI is the other product).
O
I
O
SH
10. cyclic alkane, propyl side chainDraw all the possible monochloro products of aSUBSTITUTION reaction of the H’s in your moleculewith Cl2(HCl is the other product).
ClClClCl ClCl
11. aldehyde, aryl alcohol (phenol)Draw the product of an ADDITION reaction to thealdehyde double bond with water to form a moleculethat has 2 OH groups on the same carbon.
HOOHHOOHOH
12. five carbon carboxylic acid, amineDraw the product of an internal ACID/BASE reactionof your molecule.
OHOH
2
NOOH
3
N
13. aryl amideDraw the product of a SUBSTITUTION reaction of ONE of the aryl H’s in your molecule with Cl2(theother product will be HCl).
NH
2
ONH
2
OCl
14. eight carbon acid chlorideDraw the product of a SUBSTITUTION reaction of theCl of your molecule with MeOH (the other product will be HCl; what functional group is formed?)
ClOOO
 
15. primary nitrile, tertiary fluorideDraw the product of an ADDITION reaction of H2tothe carbon-nitrogen triple bond of your molecule. ThenADD another H2to that molecule to get a thirdstructure.
NFFNHFNH
2
16. vinyl bromide, primary bromideDraw the product of a SUBSTITUTION reaction of the primary bromo group of your molecule with KC
≡
 N(potassium cyanide, the other product will be KBr.)
Br Br CNBr 
17. aryl iodide, aryl carboxylic acidDraw the product of a SUBSITUTION reaction of ONEof the aryl H’s in your molecule with a nitro group.
HO
2
C
I
HO
2
C
I
NO
2
18. six carbons, alkene, tertiary alcoholDraw all possible products of an ELIMINATIONreaction of your molecule in which H2O is eliminated.
OH
19. aryl chloride group, secondary chlorideDraw the product of an ELIMINATION reaction of your molecule in which HCl is eliminated from thealkyl piece.
ClClClCl
20. cyclic alkane, tertiary bromide, Draw the product of a SUBSTITUTIONsecondary bromidereaction involving the 2° bromo of your molecule andLiI (the other product will be LiBr).
Br Br Br 
I
21. benzylic secondary alcohol, aryl sulfideDraw the product of an ELIMINATION reaction inwhich H2is eliminated from the C-O alcohol bond of your molecule (what is the functional group formed?)
OHSOS
22. alkene, alkyl groups on all sp2carbonsDraw all possible products of an ADDITION reactionof HBr to your molecule.
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