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Name …………………………………………………………………………………Date……………………..Class……………No……
Exercise 1: Organic Chemistry and Hydrocarbons

   1. What is organic chemistry? __________________________________________________

   2. Organic compounds that contain only carbon and hydrogen are called_____________________ .

   3. Is the following sentence true or false? Alkanes contain only single covalent bonds. ____________

   4. What is the simplest alkane? ______________________

   5. Circle the letter of each statement that is true about carbon’s ability to form bonds.
         a. Carbon atoms have four valence electrons.
         b. Carbon atoms always form three covalent bonds.
         c. Carbon atoms can form stable bonds with each other.

Straight-Chain Alkanes
   6. What are straight-chain alkanes? ______________________________________________

   7. The names of all alkanes end with the suffix ______________________ .

Match the name of the straight-chain alkane with the number of carbon atoms it contains.

        _______ 8. nonane                a. 3

        _______ 9. propane               b. 4

        _______ 10. heptane              c. 7

        _______ 11. butane               d. 9

Hydrocarbon Compounds
  12. Circle the letter of each condensed structural formula for pentane.
       a. C5H12
       b. CH3CH2CH2CH2CH3
       c. CH3(CH2)3CH3
       d. C — C — C — C — C

   13. The ______________________ system names organic compounds according to their structure.




                                                                                                      1
Branched-Chain Alkane

  14. Is the following sentence true or false? Hydrogen atoms are the only atoms that can bond to the

       carbon atoms in a hydrocarbon. ______________________

  15. A(n) ______________________ is an atom or group of atoms that replaces hydrogen in a

       hydrocarbon.

  16. Alkyl groups are named by removing the-ane ending of the parent hydrocarbon and adding

       ______________________ to indicate that one______________________ has been removed.

  17. What is a branched-chain alkane? ____________________________________________

  18. Circle the letter of the correct IUPAC name for the molecule below.
                                 a. 2,2,4-triethylpentane
                                 b. 3-methylpentane
                                 c. 2,2,4-trimethylpentane



  19. Draw a condensed structural formula for 2-methylhexane.




  Properties of Alkanes

  20. Is an alkane polar or nonpolar? ______________________




                                                                                                        2
Name …………………………………………………………………………………Date……………………..Class……………No……
Exercise 2: Hydrocarbon Compounds
Alkene
   1. What is an alkene? ________________________________________________________________

  2. Organic compounds that contain fewer than the maximum number of hydrogens in their

      structures are called ______________________ compounds.

  3. Which family of hydrocarbons are always saturated compounds?______________________

  4. Circle the letter of the correct name for the alkene shown below.




      a. 2,3-dimethyl-3-pentene                c. 2,3-dimethyl-2-pentene
      b. 2-methyl-3-methyl-2-pentene           d. 3-ethyl-2-methyl-2-butene

  5. Is the following sentence true or false? Rotation can occur around a carbon–carbon double bond.

      __________

  Alkynes
  6. Hydrocarbons that contain one or more ______________________ covalent bonds between
      carbons are called alkynes.

  7. ______________________ is the simplest alkyne, and is also known by the common name

      ______________________ .

  8 Complete the table below with the names of the indicated alkanes, alkenes,and alkynes. For the
  alkenes and alkynes, assume that the multiple bond occurs between the first two carbons.

    Number of carbons              Alkane                   Alkene                 Alkyne
           C6

            C7

            C8




                                                                                                       3
Exercise 3: Isomerism
Structural Isomers
   1. What are structural isomers?

   ______________________________________________________________________________

   ______________________________________________________________________________

   2. Is the following sentence true or false? Structural isomers have the same physical properties.

        ___________

   3. How many structural isomers are there for C4H10? ______________________

   Draw a condensed structural formula for the isomers




   4. Name the structural isomers of C4H10. ___________________________________



   Geometric Isomers
   5. Molecules that differ only in the spatial configuration of their substituted groups are called

        ______________________ isomers.

   6. What two things need to be present for the type of isomerism described in Question 5 to occur?

        a. _________________________________________________________

        b. _________________________________________________________

   7. What are the names of the molecules represented by the ball-and-stick models below?




                __________________________                __________________________
                                                                                                       4
Name …………………………………………………………………………………Date……………………..Class……………No……
Exercise 4: Hydrocarbon Compounds
Draw the expanded and condensed structural formulas for the following compounds:

    Compounds              Expanded structural formulas        Condensed structural
                                                                    formulas
  2-methylpentane




  3-methylpentane




    3-methyl-4,4-
   diethylheptane



   6-methyl-3-octane




  chloromethane




   cyclopentane




     3-hexene




 2-ethyl-4-methyl-1-
      pentene




                                                                                      5
Compounds            Expanded structural formulas   Condensed structural
                                                              formulas
    trans-2-butene



     cis-2-butene




      trans-1,2-
   dichloroethene



cis-1,2-dichloroethene




   trans-2-pentene



   4-ethyl-trans-2-
      heptene


      1-propyne



      3-heptyne



4,4-dimethyl-1-hexyne




6-ethyl-3,5-dimethyl-1-
        octyne




                                                                                6
Name …………………………………………………………………………………Date……………………..Class……………No……
Exercise 5: Hydrocarbon Rings
Cyclic Hydrocarbons
   1. What is a cyclic hydrocarbon?

  ______________________________________________________________________________

  2. The most abundant cyclic hydrocarbons contain ______________________ or

      ______________________ carbons.

  3. What are the names of the cyclic hydrocarbons represented below?




      _____________            _____________           _____________           _____________

  4. Is the following sentence true or false? Cyclic hydrocarbons that contain only single carbon–carbon

      bonds are called cycloalkanes. ______________________

  5. Circle the letter of each compound that is an aliphatic compound.
        a. cycloheptane
        b. butane
        c. acetylene
        d. 2-methylpropane

Aromatic Hydrocarbons

  6. Is the following sentence true or false? Any substance that has carbon–carbon bonding

      like that of benzene is called an aromatic compound. ______________________

  7. What does it mean to say that benzene exhibits resonance?

      ______________________________________________________________________________



                                                                                                       7
8. Molecules that exhibit resonance are more ______________________ than similar molecules.

   9. When ______________________ is a substituent on an alkane, it is called a phenyl group.

   10. What is the chemical formula for a phenyl group? ______________________

   11. Circle the letter of the name of the compound shown below.
                                          a. ethylhexene
                                          b. dimethylbenzene
                                          c. ethylbenzene

   12. Derivatives of benzene that have ______________________ substituents are called disubstituted
        benzenes.



   13. Why do disubstituted benzenes always have three structural isomers?

   ______________________________________________________________________________

   ______________________________________________________________________________



Match the terms for naming a disubstituted benzene with the substituent positions
they represent.

       _______ 14. meta                a. 1,2

       _______ 15. ortho               b. 1,3

       _______ 16. para                c. 1,4




                                                                                                  8
Name …………………………………………………………………………………Date……………………..Class……………No……
Exercise 6: Reactions of Hydrocarbons
Write a balanced chemical equation for the reactions given below
   1. propane + bromine

      ___________________________________________________________________________

  2. benzene + chlorine

      ___________________________________________________________________________

  3. ethane + (2 mol) iodine

      ___________________________________________________________________________

  4. butane + fluorine

      ___________________________________________________________________________

  5. 2-butene + hydrogen

      ___________________________________________________________________________

  6. 2-pentene + hydrogen chloride

      ___________________________________________________________________________

  7. 2-methyl-2-pentene + hydrogen chloride

      ___________________________________________________________________________

  8. 1-hexene + fluorine

      ___________________________________________________________________________

  9. 2-methyl-2-hexene + water

      ___________________________________________________________________________

  10. 2-butyne + chlorine

      ___________________________________________________________________________
                                                                                    9
11. 4,4-dimethyl-2-pentyne + bromine

    ___________________________________________________________________________

12. 4,5-dimethyl-2-hexyne + (2 mol) water

    ___________________________________________________________________________




                                                                                  10
Name …………………………………………………………………………………Date……………………..Class……………No……
     Exercise 7: Derivatives of Hydrocarbon
     1. Classify the following alcohols and give the IUPAC names:


                                              OH
                                                                        CH 3                OH
       H2          H2
       C           C           H 3C          CH
HO           C          CH 3            C          CH 3     HO          CH            H3C   C      CH 3
             H2                         H2
                                                                   C           CH 3
                                                                   H2                       CH 3    D
            A                                B                           C

     _____________                    _____________              ____________           _____________




     2. Draw the figure for hydrogen bonding between two ethanol molecules.




     3. a) Write the structure for dimethyl ether and diethyl ether.




       b) Is hydrogen bonding between ether molecules possible? _____________



                                                                                                          11
4. Fill in the blanks

      Type              Structural formula   IUPAC name        Common name

    Alcohol                 CH3CH2OH                            Ethyl alcohol

                          CH3CH2CH2OH                           Propyl alcohol

                                              2-propanol

                                             cyclohexanol             -

     Ether                  CH3OCH3                -

                                                   -          Methyl ethyl ether

                         CH3CH2OCH2CH3             -

   Aldehyde                                   Methanal          Formaldehyde

                                                                Acetaldehyde

                                               Propanal

    Ketone                                   2-pentanone     Methyl propylketone

                                                                Diethylketone

Carboxylic acid              HCO2H                               Formic acid

                            CH3CO2H          Ethanoic acid

                                             Butanoic acid       Butyric acid



     Ester              CH3CH2CH2COOCH3                        Methyl butyrate



                                                                Ethyl butyrate




                                                                                   12
Type    Structural formula   IUPAC name            Common name

Amine        CH3NH2          Aminomethane

                             Aminoethane            Ethylamine

        CH3CH2NHCH2CH3       Ethylaminoethane

Amide       HCONH2           Methanamide

          CH3CH2CONH2                              Propionamide

        CH3CH2CONHCH3        N-methylpropanamide

        CH3CH2CON(CH3)2      N,N-
                             dimethylpropanamide




                                                                  13
5. Complete and balance the following reactions. Name the ester produced.

    a) butanoic acid + ethanol



    ______________________________________________________________________________




    b) propanoic acid + methanol



    ______________________________________________________________________________




    c) butanoic acid + 1-butanol



    ______________________________________________________________________________

    d) benzoic acid + methanol



    ______________________________________________________________________________



    e) benzoic acid + 3-methyl-1-butanol



    ______________________________________________________________________________




                                                                                14
15

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Chem iv exercise 2011 unit1

  • 1. Name …………………………………………………………………………………Date……………………..Class……………No…… Exercise 1: Organic Chemistry and Hydrocarbons 1. What is organic chemistry? __________________________________________________ 2. Organic compounds that contain only carbon and hydrogen are called_____________________ . 3. Is the following sentence true or false? Alkanes contain only single covalent bonds. ____________ 4. What is the simplest alkane? ______________________ 5. Circle the letter of each statement that is true about carbon’s ability to form bonds. a. Carbon atoms have four valence electrons. b. Carbon atoms always form three covalent bonds. c. Carbon atoms can form stable bonds with each other. Straight-Chain Alkanes 6. What are straight-chain alkanes? ______________________________________________ 7. The names of all alkanes end with the suffix ______________________ . Match the name of the straight-chain alkane with the number of carbon atoms it contains. _______ 8. nonane a. 3 _______ 9. propane b. 4 _______ 10. heptane c. 7 _______ 11. butane d. 9 Hydrocarbon Compounds 12. Circle the letter of each condensed structural formula for pentane. a. C5H12 b. CH3CH2CH2CH2CH3 c. CH3(CH2)3CH3 d. C — C — C — C — C 13. The ______________________ system names organic compounds according to their structure. 1
  • 2. Branched-Chain Alkane 14. Is the following sentence true or false? Hydrogen atoms are the only atoms that can bond to the carbon atoms in a hydrocarbon. ______________________ 15. A(n) ______________________ is an atom or group of atoms that replaces hydrogen in a hydrocarbon. 16. Alkyl groups are named by removing the-ane ending of the parent hydrocarbon and adding ______________________ to indicate that one______________________ has been removed. 17. What is a branched-chain alkane? ____________________________________________ 18. Circle the letter of the correct IUPAC name for the molecule below. a. 2,2,4-triethylpentane b. 3-methylpentane c. 2,2,4-trimethylpentane 19. Draw a condensed structural formula for 2-methylhexane. Properties of Alkanes 20. Is an alkane polar or nonpolar? ______________________ 2
  • 3. Name …………………………………………………………………………………Date……………………..Class……………No…… Exercise 2: Hydrocarbon Compounds Alkene 1. What is an alkene? ________________________________________________________________ 2. Organic compounds that contain fewer than the maximum number of hydrogens in their structures are called ______________________ compounds. 3. Which family of hydrocarbons are always saturated compounds?______________________ 4. Circle the letter of the correct name for the alkene shown below. a. 2,3-dimethyl-3-pentene c. 2,3-dimethyl-2-pentene b. 2-methyl-3-methyl-2-pentene d. 3-ethyl-2-methyl-2-butene 5. Is the following sentence true or false? Rotation can occur around a carbon–carbon double bond. __________ Alkynes 6. Hydrocarbons that contain one or more ______________________ covalent bonds between carbons are called alkynes. 7. ______________________ is the simplest alkyne, and is also known by the common name ______________________ . 8 Complete the table below with the names of the indicated alkanes, alkenes,and alkynes. For the alkenes and alkynes, assume that the multiple bond occurs between the first two carbons. Number of carbons Alkane Alkene Alkyne C6 C7 C8 3
  • 4. Exercise 3: Isomerism Structural Isomers 1. What are structural isomers? ______________________________________________________________________________ ______________________________________________________________________________ 2. Is the following sentence true or false? Structural isomers have the same physical properties. ___________ 3. How many structural isomers are there for C4H10? ______________________ Draw a condensed structural formula for the isomers 4. Name the structural isomers of C4H10. ___________________________________ Geometric Isomers 5. Molecules that differ only in the spatial configuration of their substituted groups are called ______________________ isomers. 6. What two things need to be present for the type of isomerism described in Question 5 to occur? a. _________________________________________________________ b. _________________________________________________________ 7. What are the names of the molecules represented by the ball-and-stick models below? __________________________ __________________________ 4
  • 5. Name …………………………………………………………………………………Date……………………..Class……………No…… Exercise 4: Hydrocarbon Compounds Draw the expanded and condensed structural formulas for the following compounds: Compounds Expanded structural formulas Condensed structural formulas 2-methylpentane 3-methylpentane 3-methyl-4,4- diethylheptane 6-methyl-3-octane chloromethane cyclopentane 3-hexene 2-ethyl-4-methyl-1- pentene 5
  • 6. Compounds Expanded structural formulas Condensed structural formulas trans-2-butene cis-2-butene trans-1,2- dichloroethene cis-1,2-dichloroethene trans-2-pentene 4-ethyl-trans-2- heptene 1-propyne 3-heptyne 4,4-dimethyl-1-hexyne 6-ethyl-3,5-dimethyl-1- octyne 6
  • 7. Name …………………………………………………………………………………Date……………………..Class……………No…… Exercise 5: Hydrocarbon Rings Cyclic Hydrocarbons 1. What is a cyclic hydrocarbon? ______________________________________________________________________________ 2. The most abundant cyclic hydrocarbons contain ______________________ or ______________________ carbons. 3. What are the names of the cyclic hydrocarbons represented below? _____________ _____________ _____________ _____________ 4. Is the following sentence true or false? Cyclic hydrocarbons that contain only single carbon–carbon bonds are called cycloalkanes. ______________________ 5. Circle the letter of each compound that is an aliphatic compound. a. cycloheptane b. butane c. acetylene d. 2-methylpropane Aromatic Hydrocarbons 6. Is the following sentence true or false? Any substance that has carbon–carbon bonding like that of benzene is called an aromatic compound. ______________________ 7. What does it mean to say that benzene exhibits resonance? ______________________________________________________________________________ 7
  • 8. 8. Molecules that exhibit resonance are more ______________________ than similar molecules. 9. When ______________________ is a substituent on an alkane, it is called a phenyl group. 10. What is the chemical formula for a phenyl group? ______________________ 11. Circle the letter of the name of the compound shown below. a. ethylhexene b. dimethylbenzene c. ethylbenzene 12. Derivatives of benzene that have ______________________ substituents are called disubstituted benzenes. 13. Why do disubstituted benzenes always have three structural isomers? ______________________________________________________________________________ ______________________________________________________________________________ Match the terms for naming a disubstituted benzene with the substituent positions they represent. _______ 14. meta a. 1,2 _______ 15. ortho b. 1,3 _______ 16. para c. 1,4 8
  • 9. Name …………………………………………………………………………………Date……………………..Class……………No…… Exercise 6: Reactions of Hydrocarbons Write a balanced chemical equation for the reactions given below 1. propane + bromine ___________________________________________________________________________ 2. benzene + chlorine ___________________________________________________________________________ 3. ethane + (2 mol) iodine ___________________________________________________________________________ 4. butane + fluorine ___________________________________________________________________________ 5. 2-butene + hydrogen ___________________________________________________________________________ 6. 2-pentene + hydrogen chloride ___________________________________________________________________________ 7. 2-methyl-2-pentene + hydrogen chloride ___________________________________________________________________________ 8. 1-hexene + fluorine ___________________________________________________________________________ 9. 2-methyl-2-hexene + water ___________________________________________________________________________ 10. 2-butyne + chlorine ___________________________________________________________________________ 9
  • 10. 11. 4,4-dimethyl-2-pentyne + bromine ___________________________________________________________________________ 12. 4,5-dimethyl-2-hexyne + (2 mol) water ___________________________________________________________________________ 10
  • 11. Name …………………………………………………………………………………Date……………………..Class……………No…… Exercise 7: Derivatives of Hydrocarbon 1. Classify the following alcohols and give the IUPAC names: OH CH 3 OH H2 H2 C C H 3C CH HO C CH 3 C CH 3 HO CH H3C C CH 3 H2 H2 C CH 3 H2 CH 3 D A B C _____________ _____________ ____________ _____________ 2. Draw the figure for hydrogen bonding between two ethanol molecules. 3. a) Write the structure for dimethyl ether and diethyl ether. b) Is hydrogen bonding between ether molecules possible? _____________ 11
  • 12. 4. Fill in the blanks Type Structural formula IUPAC name Common name Alcohol CH3CH2OH Ethyl alcohol CH3CH2CH2OH Propyl alcohol 2-propanol cyclohexanol - Ether CH3OCH3 - - Methyl ethyl ether CH3CH2OCH2CH3 - Aldehyde Methanal Formaldehyde Acetaldehyde Propanal Ketone 2-pentanone Methyl propylketone Diethylketone Carboxylic acid HCO2H Formic acid CH3CO2H Ethanoic acid Butanoic acid Butyric acid Ester CH3CH2CH2COOCH3 Methyl butyrate Ethyl butyrate 12
  • 13. Type Structural formula IUPAC name Common name Amine CH3NH2 Aminomethane Aminoethane Ethylamine CH3CH2NHCH2CH3 Ethylaminoethane Amide HCONH2 Methanamide CH3CH2CONH2 Propionamide CH3CH2CONHCH3 N-methylpropanamide CH3CH2CON(CH3)2 N,N- dimethylpropanamide 13
  • 14. 5. Complete and balance the following reactions. Name the ester produced. a) butanoic acid + ethanol ______________________________________________________________________________ b) propanoic acid + methanol ______________________________________________________________________________ c) butanoic acid + 1-butanol ______________________________________________________________________________ d) benzoic acid + methanol ______________________________________________________________________________ e) benzoic acid + 3-methyl-1-butanol ______________________________________________________________________________ 14
  • 15. 15