Chemistry 130 Oregon State University

Worksheet 5 Notes Dr. Richard Nafshun

1.
Cl

+ Cl2

Chlorine is an ortho/para director so...

Cl Cl
Cl
+

Cl

2.

NO2

+ Cl2

The nitro group is a meta director so...

NO2

Cl
3.
O
C H

+ MnO4-

O
C OH

4. Give the name and chemical formula for each of the following heterocyclic compounds:

N O O

pyridine furan

5. Which has the lowest boiling point, propane or 1-propanol? Explain.

Propane because the alcohol exhibits hydrogen bonding.

6. Which is least soluble in water, pentanol (F.M. = g/mol) or ethanol (F.M. = g/mol)?
Explain.

The longer alcohol is least soluble—more insoluble CH2 groups.

7.
K2Cr2O7
CH3CH2CH2OH
H2SO4

8. What are the products formed when 2-butanol is heated to 170 ºC with a strong acid
catalyst? [Elimination]

OH H2SO4
CH3CH2CHCH3

9. What are the products formed when 1-butanol is heated to 140 ºC with a strong acid
catalyst? [Think ether]

H2SO4
CH3CH2CH2CH2OH + CH3CH2CH2CH2OH

O
10. Phenol is sometimes called phenyl alcohol. Draw the structure and explain.

Phenyl is the C6H5 group (benzene without a hydrogen).

OH

phenol

11. The common name of CH3CH2CH2OCH2CH3 is ethyl propyl ether. The IUPAC name is
ethoxypropane.

The common name of CH3OCH2CH3 is ethyl methyl ether. What is the IUPAC name?

Methoxyethane.

12. The common name of CH3CH2OCH2CH3 is diethyl ether. What is the common name of
CH3CH2CH2CH2CH2OCH2CH2CH2CH2CH3 ?

Dipentyl ether.

13. For approximately equal formula masses, which would have the lowest boiling point, an
alkane, an ether, or al alcohol? Explain.

The alkane (non-polar and no hydrogen bonding). The ether would boil intermediately
(polar but no hydrogen bonding). The alcohol would boil at the highest temperature
(hydrogen bonding).

14. Consider a beaker that contains an alkane, an ether, an alcohol, and water. What
hydrogen bonding is possible?

Between alcohol molecules, between water molecules, between water and alcohol
molecules, and it can be said that water or an alcohol could hydrogen bond to an ether
(the lone pair of electrons on the oxygen, but the ether does not have an electron deprived
hydrogen).

15. True or false? Ethers are similar to alcohols in chemical reactivity. Well, they undergo
different chemical reactions but both are considered quite reactive.
16. Name CH3CH2CH2CH2CH2SH. What functional group is present?

The R-SH group is a thiol (AKA thio alcohol).

17. CH3CH2-S-S-CH2CH3 is diethyl disulfide. When it is reduced two ethyl mercaptan (AKA
ethanethiol) molecules are formed.

What is the name of CH3CH2CH2-S-S-CH2CH2CH3 ? Dipropyl disulfide. When it is

reduced two propyl mercaptan molecules are formed.

18. CH3CH2CH2-S-CH2CH2CH3 is a thioether. Explain the name. CH3CH2CH2-O-

CH2CH2CH3 is an ether. The thioether has an oxygen rather than an oxygen).