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Learning Commons

 
`  
 
 
3  

Alkynes

A m i d es

s
at ic
m
Ar o

Hydration of Alkenes

T hio
ls s
Salt

Acetal Formation

 
 
5  

USER  GUIDE   7    

UNIT  I     9  
ACIDS  &  BASES   11  
1.1 –  ACIDS  &  BASE  CHEMISTRY   13  
1.2  –  GRAM  EQUIVALENTS-­‐NORMALITY-­‐TITRATION     15  
1.3 –  PH    -­‐  POH  –  [H+]  –  [-­‐OH]   17  
1.4 –  BUFFERS   19  
 
ALKANES   21  
1.5 –  NAMING  ALKANES   23  
1.6 –  FUNCTIONAL  GROUPS   25  
1.7 –  DRAWING  STRUCTURES   27  
1.8 –  CONFORMERS  &  ISOMERS   29  
 
PRACTICE  TESTS    
1A   31  
1B   39  
 
 
 

UNIT  II       47  
ALKENES,  ALKYNES  &  AROMATICS   49  
2.1  –  NAMING  ALKENES,  ALKYNES,  &  AROMATICS   51  
2.2  –  CIS/TRANS   53    
2.3  –  POLYMERS     55  
2.4  –  REACTIONS  OF  ALKENES,  ALKYNES,  &  AROMATICS   57  
 
ALCOHOLS,  PHENOLS,  ETHERS,  THIOLS,  &  HALOGENS   59  
2.5  –  NAMING  ALCOHOLS,  PHENOLS,  ETHERS,  THIOLS,  &  HALOGENS   61  
2.6  –  REACTIONS  OF  ALCOHOLS,  PHENOLS,  ETHERS,  THIOLS,  &  HALOGENS   63  
 
PRACTICE  TESTS  
2A   65    
2B   73    
 
 
 
 

UNIT  III   81  
AMINES,  ALDEHYDES,  KETONES,  CARBOXYLIC  ACIDS,  ESTERS,  &  AMIDES   83  
3.1  –  NAMING  AMINES,  ALDEHYDES,  &  KETONES   85  
3.2  –  NAMING  CARBOXYLIC  ACIDS,  ESTERS,  &  AMIDES   87  
3.3  –  REACTIONS  –  TESTS  (LUCAS,  BENEDICTS,  &  TOLLENS)   89  
3.4  –  REACTIONS  OF  CARBONYLS   91  
 
CARBOHYDRATES   93  
3.5  –  CARBOHYDRATE  NOMENCLATURE   95  
3.6  –  REACTIONS  OF  CARBOHYDRATES   97  
3.7  –  CONVERTING  FISCHER  TO  CYCLIC   99  
 
PRACTICE  TESTS  
3A   101  
3B   109  
 
 
 

TOOLS   117  
NOMENCLATURE   119  
COMMON  FUNCTIONAL  GROUPS   120  
SIGNIFICANT  FIGURES   121  
PERIODIC  TABLE  OF  THE  ELEMENTS   123  
 
 
 
   

 
 
7  
 
 

Thank   you   for   choosing   to   use   this   workbook   provided   by   the   PLUS   program   at   Eastern  
Washington  University!     The  purpose  of   this  book  is  to  provide  a  medium  to  which  students  
and  tutors  can  enhance  their   subject  knowledge  by  focusing   on  fluency  and  speed,  which  are  
fundamental   to   success   on   exams.     This   workbook   is   intended   for   use   by   a   tutor   who   has  
successfully  completed  the  course  in  question,  in  a  1-­‐on-­‐1  or  small  group  format.    In  addition,  
this   workbook   assumes   that   the   reader   has   access   to   a   textbook   for   explanations   not  
provided  in  this  material.    This  book  is  intended  to  be  supplemental  to  a  textbook  for  use  by  a  
tutor  and  a  student.  
NO TE:
 
These worksheets and
Worksheets:   practice exams are
Ø 1  page  of  problems  on  a  focused  topic   intended to be used with
Ø FRONT  =  BLANK   a knowledgeable tutor
Ø BACK  =  ANSWER  KEY   and therefore, the most
Ø Print  off/copy  for  student   problems encountered
Ø Or  work  on  with  student   are NOT meant to be
Ø Consult  textbook  for  detailed  explanation  of  topic   easy.
 
Practice  Exams:   The theory: if a student
Ø 3-­‐4  pages  of  simulated  exam  type  questions   can complete difficult
o There  are  two  types  of  exams:   practice problems with a
§ A  –  very  similar  to  worksheets   tutor, they can excel
§ B  –  more  integrative  concepts  &  analysis   independently on a
Ø TREAT  IT  LIKE  A  REAL  EXAM   standard exam level.
o Grab  a  study  carrel  or  another  quite  place  
o No  drinks/food,  cell  phones,  textbooks,  or  computers  
Ø Allow  no  more  than  50-­‐55  minutes  to  complete.  
Ø Answer  key  immediately  follows  the  blank  test  
Ø Grade  exam  for  students  just  like  a  professor  would  
Ø Or  grade  exam  with  student  –  learn  from  mistakes!  
 
In   order   to   get   the   most   out   of   the   practice   exams,   it   is   imperative   to   simulate   a   test-­‐like  
environment   when  taking   these  exams.   Many   students   unfortunately  suffer  from   test   anxiety  
and   much   of   this   anxiety   can   be   avoided   by   increased   knowledge   of   material,   as   well   as  
experience   with   testing   environments.   Once   the   student   has   completed   an   exam,   the   tutor  
may   choose   to   grade   the   exam   during   a   normal   session   while   the   student   works   on   other  
materials   (such   as   worksheets)  and   return  the  graded  exam  to  the  student.  Alternatively,   a  
tutor  could   evaluate  the  exam  with  the  student.     It  is   not  advised,   however,   to  simply  provide  
the   student   with   the   answer   key   without   a   tutor   to   review   the   exam   also.     This   is   due   the  
simple  fact  that  it   is  hard  to  catch  our  own  mistakes.    Also,  because  the  practice  exam  does  
not   directly   affect   the   student’s   course   grade,   the   path   of   least   resistance   (neglecting   to  
evaluate)  is  easy   to   be  taken.      The   point  of  this  book  is  to  help  identify  problem  areas   and  
provide  a  means  to  address  and  remedy  them.    
Happy tutoring!
 
81  
 
83  

Aldehydes   Ketones  
• Replace  the  ‘e’   • Replace  the  ‘e’  
at  the  end  of  the   at  the  end  of  the  
parent  chain   parent  chain  
with  “al.”   with  “one.”    

Carboxylic  Acids   Esters  


• Replace  the  ‘e’   • 1st  the  name  of  
at  the  end  of  the   alkyl  group  off  the  
parent  chain   ester.  
with  “oic  acid”.     • 2nd  the  name  of  the  
parent  acid,  replacing  “ic”  by  “ate.”  

Amines     Compounds  to  MEMORIZE  


Count  the  #  of  carbons  

Amines  
• Replace  the  ‘e’  at  the  end  of  the  
parent  chain  with  “amine.”    
• Use  a  number  to  identify  the  
location  of  the  nitrogen,  
either  before  the  parent  
name  or  before  “amine.”  
• The  name  of  any  alkyl  group  bonded  to  the  nitrogen  is  
preceded  by  an  “N.”    

Amides  
• 1st  name  alkyl  
group  off  the  
amide  preceding  
with  “N.”  
• 2nd  name  parent  
acid,  replacing  “ic”  with  “amide.”  
 
85  

3.1 – Worksheet
Naming Amines, Aldehydes, & ketones
Please  complete  the  following  table  by  either  providing  the  structure  or  the  name  of  the  
compound.    

     

     

     

 
  Formaldehyde  
 

     

N,N-­‐diethyl-­‐5-­‐fluoroheptan-­‐3-­‐
2-­‐chloro-­‐3-­‐methylhexanal    
amine  

     

3,4-­‐diethyl-­‐3-­‐methyl-­‐2-­‐
   
hexanone  

     

    5-­‐bromo-­‐3-­‐methylheptanal  
 
 

3.1 – Worksheet – KEY


Naming Amines, Aldehydes, & ketones
Please  complete  the  following  table  by  either  providing  the  structure  or  the  name  of  the  
compound.    

     

Ethylpropylamine   4,4,-­‐dimethylpentanal   Acetone  

     

2-­‐ethyl-­‐N-­‐isopropyl-­‐N-­‐
3-­‐methylcyclohexanone   Formaldehyde  
methylcyclohexanamine  

     

N,N-­‐diethyl-­‐5-­‐fluoroheptan-­‐3-­‐ 5-­‐bromo-­‐2-­‐methyl-­‐4-­‐
2-­‐chloro-­‐3-­‐methylhexanal  
amine   heptanone  

     

3,4-­‐diethyl-­‐3-­‐methyl-­‐2-­‐ N-­‐sec-­‐butyl-­‐2-­‐tert-­‐butyl-­‐N-­‐
Acetalaldehyde  
hexanone   isobutylcyclopentanamine  

     

3-­‐chloro-­‐5-­‐
5-­‐ethyl-­‐6-­‐methyl-­‐4-­‐octanone   5-­‐bromo-­‐3-­‐methylheptanal  
cyclobutylbenzaldehyde  
 
87  
3.2 – Worksheet
Naming Carboxylic Acids, Amides, & Esters
Please  complete  the  following  table  by  either  providing  the  structure  or  the  name  of  the  
compound.    

     

 
   
 

     

 
  N,N,3-­‐triethylpentanamide  
 

     

 
Butyl  octanoate    
 

     

3-­‐cyclcohexyl-­‐N-­‐isopropyl-­‐ 3-­‐chloro-­‐4-­‐cyclopropyl-­‐2-­‐
 
N,2,4-­‐trimethyloctanamide   isopropylpentoic  acid  

     

4-­‐ethyl-­‐5-­‐methyl-­‐N,N-­‐ 2-­‐ethyl-­‐6-­‐iodo-­‐3,3-­‐
 
dipropylheptanamide   dimethylheptanoic  acid  
 
 
3.2 – Worksheet – KEY
Naming Carboxylic Acids, Amides, & Esters
Please  complete  the  following  table  by  either  providing  the  structure  or  the  name  of  the  
compound.    

     

4-­‐  fluoro-­‐N-­‐methyl-­‐
Ethyl  3-­‐methylpentanoate   3-­‐chlorobutanoic  acid  
hexanamide  

     

Pentyl  3-­‐propyl-­‐6-­‐
4-­‐methylpentanamide   N,N,3-­‐triethylpentanamide  
bromohexanoate  

     

Butyl  3-­‐bromo-­‐3-­‐ 4-­‐chloro-­‐3-­‐propyl-­‐4-­‐


Butyl  octanoate  
isobutylpentanoate   methylpentanoic  acid  

     

Cyclopentyl  5-­‐ethyl-­‐3-­‐ 3-­‐cyclcohexyl-­‐N-­‐isopropyl-­‐ 3-­‐chloro-­‐4-­‐cyclopropyl-­‐2-­‐


methyloctanoate   N,2,4-­‐trimethyloctanamide   isopropylpentoic  acid  

     

4-­‐ethyl-­‐5-­‐methyl-­‐N,N-­‐ 2-­‐tert-­‐butyl-­‐3-­‐ 2-­‐ethyl-­‐6-­‐iodo-­‐3,3-­‐


dipropylheptanamide   isopropylhexanoic  acid   dimethylheptanoic  acid  
 
89  
3.3 – Worksheet
Reactions – Tests (Lucas, Benedicts, & Tollens)
Please  provide  the  name  of  the  following  tests  as  well  as  the  reactants,  products,  or  starting  
materials.    

Name:    
+  

+   Name:    

A  Lucas  test  is  performed  on  the  following  alcohols  to  determine  if  the  presence  of  a  primary,  
secondary,  or  tertiary  alcohol.    Using  your  knowledge  of  the  Lucas  test  please  identify  which  
alcohol  is  in  which  beaker.      

Beaker  A:  No  precipitation  after  one  hour  __________________________________  


Beaker  B:  Precipitation  observed  after  four  minutes  ______________________  
Beaker  C:  Precipitation  observed  immediately  _____________________________  
 
Write  the  reaction  that  occurs  in  beaker  C:  

Perform  a  Benedicts  test  on  the  following  compound.    Make  sure  to  list  all  reagents  and  the  
expected  products  &  colors  associated.    

+  

Perform  a  Tollens  test  on  the  following  compound,  make  sure  to  list  all  reagents  and  the  
expected  products  &  colors  associated.    

+  
 
3.3 – Worksheet – KEY
Reactions – Tests (Lucas, Benedicts, & Tollens)
Please  provide  the  name  of  the  following  tests  as  well  as  the  reactants,  products,  or  starting  
materials.    

Name:  Tollens  Test  


+  

+   Name:  Benedicts  Test  

A  Lucas  test  is  performed  on  the  following  alcohols  to  determine  if  the  presence  of  a  primary,  
secondary,  or  tertiary  alcohol.    Using  your  knowledge  of  the  Lucas  test  please  identify  which  
alcohol  is  in  which  beaker.      

(I)  
Beaker  A:  No  precipitation  after  one  hour  __________________________________  
(III)  
Beaker  B:  Precipitation  observed  after  four  minutes  ______________________  
(II)  
Beaker  C:  Precipitation  observed  immediately  _____________________________  
 
Write  the  reaction  that  occurs  in  beaker  C:  

Perform  a  Benedicts  test  on  the  following  compound.    Make  sure  to  list  all  reagents  and  the  
expected  products  &  colors  associated.    

Buffer
+  

Perform  a  Tollens  test  on  the  following  compound,  make  sure  to  list  all  reagents  and  the  
expected  products  &  colors  associated.    

+   NH3
Ag(s)
H2O
91  
3.4 – Worksheet
Reaction s of Carbonyls
Please  complete  the  following  reactions  by  either  providing  the  reactants,  products  or  starting  
materials.    

+  

+   +  

+  

   
 
3.4 – Worksheet – KEY
Reaction s of Carbonyls
Please  complete  the  following  reactions  by  either  providing  the  reactants,  products  or  starting  
materials.    

HCN

+  

+  

+  

+   +  

+  

+  

+  
93  

 D  &  L  Sugars  
Look  at  last  chiral  carbon  
  Fischer  à  Cyclic  
If  hydroxyl  is      
on  right  –  D             RIGHT  in  Fischer  
  DOWN  in  Cyclic    
   
   
  LEFT  in  Fischer  
 If  hydroxyl  is   UP  in  Cyclic  
 on  the  left  –  L  
 
 
 
  Compounds  to  
MEMORIZE  
#  of  Stereoisomers  
 
2n  
 
n  =  #  of  chiral  carbons  

DISSACCHARIDES  to  MEMORIZE  


 
95  
3.5 – Worksheet
Carbohydrate Nomenclat ure
Please  classify  the  following  compounds  through  use  of  the  terms  aldose  and  ketose,  including  
the  #  of  carbons  in  the  name.  

Classification:     Classification:    
D  or  L:       D  or  L:      

Please  classify  the  following  compounds  through  use  of  the  terms  aldose  and  ketose,  including  
the  #  of  carbons  in  the  name.    Also,  draw  its  enantiomer  and  name  both  compounds  including  
the  appropriate  D/L  nomenclature.  

Classification:     Classification:     Classification:    


Original:     Original:     Original:    
Enantiomer:     Enantiomer:     Enantiomer:    
Please  identify  the  following  disaccharides,  the  two  monomers  that  make  up  the  disaccharides,  
and  the  types  of  glycosidic  bonds  between  them.    
Name:    
Monomers:    
Type  of  Bond:  
Name:    
Monomers:    
Type  of  Bond:    

Please  draw  Maltose.    Indicate  the  two  monomers  that  make  up  the  disaccharide  as  well  as  the  
type  of  bond  between  the  two  monomers.  Briefly  describe  what  amylose,  amylopectin,  and  
glycogen  are  and  how  amylopectin  and  glycogen  are  used  in  plants  and  animals.    
 
3.5 – Worksheet – KEY
Carbohydrate Nomenclat ure
Please  classify  the  following  compounds  through  use  of  the  terms  aldose  and  ketose,  including  
the  #  of  carbons  in  the  name.  

Classification:  Aldopentose   Classification:  Ketohexose  


D  or  L:    D   D  or  L:    L  

Please  classify  the  following  compounds  through  use  of  the  terms  aldose  and  ketose,  including  
the  #  of  carbons  in  the  name.    Also,  draw  its  enantiomer  and  name  both  compounds  including  
the  appropriate  D/L  nomenclature.  

Classification:  Aldopentose   Classification:  Aldohexose   Classification:  Ketohexose  


Original:  D-­‐Ribose   Original:  D-­‐Glucose   Original:  D-­‐Fructose  
Enantiomer:  L-­‐Ribose   Enantiomer:  L-­‐Glucose   Enantiomer:  L-­‐Fructose  
Please  identify  the  following  disaccharides,  the  two  monomers  that  make  up  the  disaccharides,  
and  the  types  of  glycosidic  bonds  between  them.    
Name:  Lactose  
Monomers:  β-­‐D-­‐Galactose  &  D-­‐Glucose  
Type  of  Bond:  β-­‐1,4  
Name:  Cellobiose  
Monomers:  β-­‐D-­‐Glucose  &  D-­‐Glucose  
Type  of  Bond:  β-­‐1,4  

Please  draw  Maltose.    Indicate  the  two  monomers  that  make  up  the  disaccharide  as  well  as  the  
type  of  bond  between  the  two  monomers.  Briefly  describe  what  amylose,  amylopectin,  and  
glycogen  are  and  how  amylopectin  and  glycogen  are  used  in  plants  and  animals.    
Amylose,  amylopectin,  and  glycogen  are  all  starches  used  
for  energy  in  living  organisms.    Amylopectin  and  glycogen  
also  have  α-­‐1,6  linkages  which  ultimately  store  more  
energy.    Amylopectin  does  not  have  as  frequent  branching  
as  glycogen.    Due  to  the  frequent  b ranching,  glycogen  holds  
more  potential  for  fast  energy,  which  is  why  it  is  used  in  
animals,  whereas  plants  use  amylopectin.  
97  
3.6 – Worksheet
Reaction s of Carbohydrates
Please  complete  the  following  reactions  by  providing  the  product(s),  reactants,  or  the  
starting  materials.    

+  

+  

Working  in  a  lab,  your  supervisor  instructs  you  to  perform  both  a  Benedicts  test  and  a  Tollens  
test  on  fructose.    You  know  that  ketones  have  to  undergo  a  rearrangement  before  they  can  be  
reduced.    Please  show  the  steps  of  the  rearrangement  then  perform  both  tests  with  the  
appropriate  reagents.    
 
3.6 – Worksheet – KEY
Reaction s of Carbohydrates
Please  complete  the  following  reactions  by  providing  the  product(s),  reactants,  or  the  
starting  materials.    

+  

+  

Working  in  a  lab,  your  supervisor  instructs  you  to  perform  both  a  Benedicts  test  and  a  Tollens  
test  on  fructose.    You  know  that  ketones  have  to  undergo  a  rearrangement  before  they  can  be  
reducing  sugars.    Please  show  the  steps  of  the  rearrangement  then  perform  both  tests  with  the  
appropriate  reagents.    

Benedicts  

+   +  

Tollens  
+   +  
99  
3.7 – Worksheet
Con vertin g Fischer to Cyclic
Please  convert  the  following  from  Fischer  to  cyclic  form.      

H O

H OH

HO H

HO H

H OH

OH

Please  convert  the  following  from  cyclic  to  Fischer.    


 
3.7 – Worksheet – KEY  
Con vertin g Fischer to Cyclic
Please  convert  the  following  from  Fischer  to  cyclic  form.      

H O

H OH

HO H

HO H

H OH

OH

Please  convert  the  following  from  cyclic  to  Fischer.    


101  
Practice T est – 3A
Please  complete  the  following  table  by  either  providing  the  compound’s  structure  or  name.  (30)  

     

 
  Isopropylisobutylamine  
 

     

 
Acetone    
 

     

 
  Isobutyl  3-­‐methylbutanoate  
 

     

 
N-­‐sec-­‐butylpropanamide    
 

     

3-­‐cyclopentyl-­‐4-­‐
  Formaldehyde  
methylhexanal  
 
 
Practice T est – 3A
2.  A  Lucas  test  is  performed  on  the  following  alcohols  to  determine  if  the  presence  of  a  primary,  
secondary,  or  tertiary  alcohol.    Using  your  knowledge  of  the  Lucas  test  please  identify  which  
alcohol  is  in  which  beaker.    (6)  

Beaker  A:  Precipitation  observed  immediately  _____________________________  


Beaker  B:  Precipitation  observed  after  four  minutes  ______________________  
Beaker  C:  No  precipitation  after  one  hour  __________________________________  
 
Write  the  reaction  that  occurs  in  beaker  A:  

3.  Please  complete  the  following  reactions  either  by  providing  the  products,  reactants,  or  
starting  materials.  (16)  

+  
103  
Practice T est – 3A
Working  in  a  lab,  your  supervisor  instructs  you  to  perform  both  a  Benedicts  test  and  a  Tollens  
test  the  following  ketohexose.    You  know  that  ketones  have  to  undergo  a  rearrangement  
before  they  can  be  reducing  sugars.    Please  show  the  steps  of  the  rearrangement  then  perform  
both  tests  with  the  appropriate  reagents.    Also,  please  name  the  ketohexose.  (12)  

Benedicts

Tollens

Name:  
Please  classify  and  identify  the  following  carbohydrates  by  name  and  provide  their  
enantiomers  structure  and  name.    Be  sure  to  include  appropriate  D  or  L  specification.  (8)  

Classification:     Classification:    
Original:     Original:    
Enantiomer:     Enantiomer:    
Please  identify  the  following  disaccharides,  the  two  monomers  that  make  up  the  disaccharides,  
and  the  types  of  glycosidic  bonds  between  them.    (8)  

Name:     Name:    
Monomers:     Monomers:    
   
Type  of  Bond:     Type  of  Bond:    
 

Practice T est – 3A
7.  Briefly  describe  what  amylose,  amylopectin,  and  glycogen  are  and  how  amylopectin  and  
glycogen  are  used  in  plants  and  animals.  (4)  

8.  Please  complete  the  following  reactions,  either  by  providing  the  products,  reactants,  or  
starting  materials.    Also,  when  prompted  provide  the  name  of  the  compound  in  question.  (8)  

(6)  

+  

Name  of  starting  material(s):     Name  of  product:    

(2)  

(4)   9.  Please  convert  the  following  compound  


H O
from  Fischer  to  cyclic  &  provide  its  name.  (4)  

H OH

HO H

H OH

H OH

OH

Name  of  starting  material:     Name:     100  


105  
Practice T est – 3A – KEY  
1.  Please  complete  the  following  table  by  either  providing  the  compound’s  structure  or  name.  (30)  

     

4-­‐chloro-­‐3-­‐ethylpentanoic  
Propyl  2-­‐bromopropanoate   Isopropylisobutylamine  
acid  

     

N-­‐ethyl-­‐3-­‐iodo-­‐2-­‐propyl-­‐N-­‐
Acetone   2,2-­‐dimethyl-­‐3-­‐ethylhexanal  
methylpentanamide  

     

N-­‐tert-­‐butyl-­‐N-­‐isopropyl-­‐2-­‐
4-­‐ethyl-­‐6-­‐fluoroheptan-­‐3-­‐one   Isobutyl  3-­‐methylbutanoate  
methylcyclopentanamine  

     

2,2,5,5-­‐Tetrachloro-­‐3-­‐
N-­‐sec-­‐butylpropanamide   Formic  Acid  
ethylcyclohexanone  

     

3-­‐cyclopentyl-­‐4-­‐ 2-­‐Iodo-­‐3-­‐propyl-­‐2-­‐
Formaldehyde  
methylhexanal   methylhexanoic  acid  
 
 
Practice T est – 3A – KEY
2.  A  Lucas  test  is  performed  on  the  following  alcohols  to  determine  if  the  presence  of  a  primary,  
secondary,  or  tertiary  alcohol.    Using  your  knowledge  of  the  Lucas  test  please  identify  which  
alcohol  is  in  which  beaker.    (6)  

II  
Beaker  A:  Precipitation  observed  immediately  _____________________________  
I  
Beaker  B:  Precipitation  observed  after  four  minutes  ______________________  
III  
Beaker  C:  No  precipitation  after  one  hour  __________________________________  
 
Write  the  reaction  that  occurs  in  beaker  A:  

3.  Please  complete  the  following  reactions  either  by  providing  the  products,  reactants,  or  
starting  materials.  (16)  

+  
107  
Practice T est – 3A – KEY  

4.  Working  in  a  lab,  your  supervisor  instructs  you  to  perform  both  a  Benedicts  test  and  a  Tollens  
test  the  following  ketohexose.    You  know  that  ketones  have  to  undergo  a  rearrangement  before  
they  can  be  reducing  sugars.    Please  show  the  steps  of  the  rearrangement  then  perform  both  tests  
with  the  appropriate  reagents.    Also,  please  name  the  ketohexose.  (12)  

Benedicts –O O

+   +   H OH

HO H

Tollens H OH

H OH
+   +  
OH

5.  Please  classify  and  identify  the  following  carbohydrates  by  name  and  provide  their  
enantiomers  structure  and  name.    Be  sure  to  include  appropriate  D  or  L  specification.  (8)  
(4)  
(4)  

Classification:  Aldohexose   Classification:  Aldopentose  


Original:  D-­‐Galactose   Original:  D-­‐Ribose  
Enantiomer:  L-­‐Galactose   Enantiomer:  L-­‐Ribose  
6.  Please  identify  the  following  disaccharides,  the  two  monomers  that  make  up  the  
disaccharides,  and  the  types  of  glycosidic  bonds  between  them.    (8)  
(4)   (4)  

Name:  Sucrose   Name:  Maltose  


Monomers:  β-­‐D-­‐Fructose  &     Monomers:  β-­‐D-­‐Glucose  
D-­‐Glucose   &  D-­‐Glucose  
Type  of  Bond:  β-­‐1,2   Type  of  Bond:  α-­‐1,4  
 
 
Practice T est – 3A – KEY
7.  Briefly  describe  what  amylose,  amylopectin,  and  glycogen  are  and  how  amylopectin  and  
glycogen  are  used  in  plants  and  animals.  (4)  
Amylose,  amylopectin,  and  glycogen  are  all  starches  used  for  energy  in  living  organisms.    
Amylopectin  and  glycogen  have  α-­‐1,6  linkages  which  ultimately  store  more  energy.    
Amylopectin  does  not  have  as  frequent  branching  as  glycogen.    Due  to  the  frequent  branching,  
glycogen  holds  more  potential  for  fast  energy,  which  is  why  it  is  used  in  animals  (fight/flight),  
whereas  plants  use  amylopectin.  
8.  Please  complete  the  following  reactions,  either  by  providing  the  products,  reactants,  or  
starting  materials.    Also,  when  prompted  provide  the  name  of  the  compound  in  question.  (8)  

(6)  

+  

Name  of  starting  material(s):  β-­‐D-­‐Galactose   Name  of  product:  Lactose  


&  D-­‐  Glucose  

OH
(2)  
OH
O
H3C

O
OH OH CH3

(4)   9.  Please  convert  the  following  compound  


H O
from  Fischer  to  cyclic  &  provide  its  name.  (4)  

H OH

HO H

H OH

H OH

OH

Name  of  starting  material:  D-­‐Glucose   Name:  2-­‐D-­‐deoxyribose  


109  

Practice T est – 3B

1.  Please  complete  the  following  reactions  by  either  providing  the  starting  materials,  reactants,  
or  product(s).    When  prompted,  please  provide  the  name  of  the  compound  in  question.  (24)  
(4)   H O (6)  

HO H

HO H
+  
H OH

OH Name:    
Name:    

(8)  

Name:     Name:     Name:    

(6)  

Name:    

2.  Ketoses  are  reducing  sugars  because  under  certain  conditions,  they  undergo  a  rearrangement  
that  allows  them  to  be  reduced.    Please  show  each  step  of  this  rearrangement  with  D-­‐  Fructose.  Be  
sure  to  include  any  inorganic  reagents  needed,  and  please  name  the  product.  (8)  

Name:    
 

Practice T est – 3B
3.  A  test  is  performed  on  2-­‐chloro-­‐3-­‐ethylpentanal  that  yields  a  silver  precipitate.    Please  
identify  which  test  was  performed  as  well  as  show  this  reaction  including  all  starting  materials,  
reactants,  and  products.  (10)  

4.  In  a  lab,  you  have  two  unlabeled  beakers  containing  either  3-­‐ethylcyclohexanone  or  2-­‐
isopropylbutanal.    Using  only  a  reduction  reaction  with  NaBH4  and  a  Lucas  test,  show  the  
reactions  that  would  help  determine  the  identity  of  the  two  beakers.    Be  sure  to  include  all  
starting  materials,  reactants,  products,  and  to  explain  your  deduction.  (12)  

5.  A  test  was  performed  on  D-­‐Galactose  that  produced  a  red  solution.    Please  identify  which  
test  was  performed  as  well  as  show  this  reaction  including  all  starting  materials,  reactants,  
and  products.  (10)  

6.  Please  provide  the  cyclic  structure  of  the  starting  materials  and  provide  the  reactants  to  this  
reaction  involving  α-­‐D-­‐Glucose.  (4)    
111  
 
Practice T est – 3B
7.  Please  complete  the  following  table  by  providing  either  the  name  or  the  structure  of  the  
compound.  (12)  

     

  Acetic  Acid    

O
     
H H

2-­‐fluoro-­‐4-­‐methylpentaonic    
 
acid    
 
8.  Please  classify  the  following  compound  as  an  aldose/ketose,  D/L  sugar,  and  then  draw  its’  
enantiomer  then  and  convert  from  the  original  Fischer  structure  to  its  cyclic  form.  (6)  

Enantiomer   Cyclic  Form  

Classification:                                                      D/L:    
7.  Briefly  describe  what  amylose,  amylopectin,  and  glycogen  are  and  how  amylopectin  and  
glycogen  are  used  in  plants  and  animals.  (4)  

8.  Please  circle  all  of  the  chiral  carbons  and  calculate  the  maximum  #  of  stereoisomers  possible.  
(4)  
 
   
Practice T est – 3B

Please  provide  the  structure  for  Lactose,  identify  the  monomers  that  make  up  the  disaccharide,  
and  provide  the  type  of  bond  between  the  two  monomers.  (6)  

100  
113  

Practice T est – 3B – KEY

1.  Please  complete  the  following  reactions  by  either  providing  the  starting  materials,  reactants,  
or  product(s).    When  prompted,  please  provide  the  name  of  the  compound  in  question.  (24)  
(4)   H O OH (6)  

HO H HO H

HO H HO H +  
H OH H OH

OH OH Name:  Cyclopentyl  2,2-­‐


Name:  D-­‐Ribose   dimethylpropanoate  

(8)  

Name:  Ethyl   Name:  2-­‐Chlorobutanoic   Name:  2-­‐Chloro-­‐N-­‐ethyl-­‐


propylamine   acid   N-­‐propylbutanamide  

(6)  

Name:  3-­‐ethyl-­‐2-­‐
hexanone  
2.  Ketoses  are  reducing  sugars  because  under  certain  conditions,  they  undergo  a  rearrangement  
that  allows  them  to  be  reduced.    Please  show  each  step  of  this  rearrangement  with  D-­‐  Fructose.  Be  
sure  to  include  any  inorganic  reagents  needed,  and  please  name  the  product.  (8)  

Name:  D-­‐Glucose  
 
 
Practice T est – 3B – KEY
3.  A  test  is  performed  on  2-­‐chloro-­‐3-­‐ethylpentanal  that  yields  a  silver  precipitate.    Please  
identify  which  test  was  performed  as  well  as  show  this  reaction  including  all  starting  materials,  
reactants,  and  products.  (10)  

Tollens  Test  

+   +  

4.  In  a  lab,  you  have  two  unlabeled  beakers  containing  either  3-­‐ethylcyclohexanone  or  2-­‐
isopropylbutanal.    Using  only  a  reduction  reaction  with  NaBH4  and  a  Lucas  test,  show  the  
reactions  that  would  help  determine  the  identity  of  the  two  beakers.    Be  sure  to  include  all  
starting  materials,  reactants,  products,  and  to  explain  your  deduction.  (12)  

Precipitate  will  
form  within  5  
minutes  

No  precipitate  
will  form  in  an  
hour  

5.  A  test  was  performed  on  D-­‐Galactose  that  produced  a  red  solution.    Please  identify  which  
test  was  performed  as  well  as  show  this  reaction  including  all  starting  materials,  reactants,  
and  products.  (10)  
H O

H OH

HO H

HO H

H OH

OH
D-Galactose

6.  Please  provide  the  cyclic  structure  of  the  starting  materials  and  provide  the  reactants  to  this  
reaction  involving  α-­‐D-­‐Glucose.  (4)    
115  
   
Practice T est – 3B – KEY
7.  Please  complete  the  following  table  by  providing  either  the  name  or  the  structure  of  the  
compound.  (12)  

     

N-­‐ethyl-­‐N-­‐methylhexan-­‐3-­‐
Acetic  Acid   Ethyl  2-­‐bromopropanoate  
amine  

     
H H

2-­‐fluoro-­‐4-­‐methylpentaonic   N,2-­‐diethyl-­‐N-­‐
Formaldehyde  
acid   methylbutanamide  
 
8.  Please  classify  the  following  compound  as  an  aldose/ketose,  D/L  sugar,  and  then  draw  its’  
enantiomer  then  and  convert  from  the  original  Fischer  structure  to  its  cyclic  form.  (6)  

Enantiomer   Cyclic  Form  

Classification:  Ketohexose                      D/L:  D  


7.  Briefly  describe  what  amylose,  amylopectin,  and  glycogen  are  and  how  amylopectin  and  
glycogen  are  used  in  plants  and  animals.  (4)  
Amylose,  amylopectin,  and  glycogen  are  all  starches  used  for  energy  in  living  organisms.    
Amylopectin  and  glycogen  have  α-­‐1,6  linkages  which  ultimately  store  more  energy.    
Amylopectin  does  not  have  as  frequent  branching  as  glycogen.    Due  to  the  frequent  branching,  
glycogen  holds  more  potential  for  fast  energy,  which  is  why  it  is  used  in  animals  (fight/flight),  
whereas  plants  use  amylopectin.  

6  chiral  centers  à  26  =  64  possible  stereoisomers  


 
       
Practice T est – 3B – KEY

Please  provide  the  structure  for  Lactose,  identify  the  monomers  that  make  up  the  disaccharide,  
and  provide  the  type  of  bond  between  the  two  monomers.  (6)  

1,4-­‐β  linkage  

100  
117  
 
119  
 
121  
 
123  
   

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