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FIRST YEAR CHEMISTRY
TABLE OF CONTENTS
Alkyl Halides. 8
Alcohols. 9
Aldehydes and Ketones. I2
Carboxylic Acids. I4
Esters. t6
Amines 18
Amides 20
Summary Problems 2I
ORGANIC FUNCTIONAL GROUPS. 22
REACTIONS OF ORGANIC COMPOUNDS........ 26
DEFINITIONS 29
Summary Table of Classesof Organic Compounds........... 32
1
This study guide is intended to supplement standard group—the part of the molecule which is responsible for
first-year texts, whose coverage of organic chemistry the characteristic chemical and physical properties of the
varies depending on the authors. Structures, nomenclature compound. For example, the general formula of alkenes is
rules, physical properties, and a few important reactions R2C = CR2, where the R's represent hydrogens or alkyl
are covered for major classes of organic compounds that groups. All alkenes undergo certain reactions that depend
contain a single functional group. Isomerism in organic primarily on the presence of the C=C bond, and not on
compounds is treated in Experiment 21 in the First Year the R groups. Functional groups and examples of each
Lab Manual. class of compound are given in the table located on the
inside back cover of this Study Guide.
The key to organic chemistry is the functional
ALKANES
CH2 CH2
H2 C CH2
H2 C CH2 long-chain alkanes
CH2
cyclopropane cyclobutane cyclohexane shorter-chain alkanes, alkenes, and H2
H2 C CH 2
H3 C C C CH 3 Problems on Alkanes
H3 C CH 3 1. Give structural formulas of the following compounds:
H H
180°
C C 4-methyl-cis-2-
H3 C CH CH 3 pentene
Nomenclature
CH 3
The IUPAC name of an alkene is derived from the 1,3-butadiene
H2 C CH CH CH 2
longest continuous sequence of carbon atoms containing
the double bond. The name of the alkene is then obtained
by dropping the -ane ending from the alkane name and CH 3
3 4 5 4 5 6
adding -ene. The position of the double bond is indicated H CH 2CH 2CH 3 H CH 2 C CH 3
1 2 2 3
by numbering the parent chain from the end that gives the C C C C CH 3
lowest possible number of the double bond. Geometric
H CH 2CH 3 H3 C H
isomers are indicated by the prefixes cis and trans. For 1
example,
2-ethyl-1-pentene trans-5,5-dimethyl-2-hexene
Common and IUPAC names are given in Table 3 for
some alkenes.
Similarly, the longest continuous sequence of carbon
atoms containing the triple bond is the basis for the parent
5
name of an alkyne. The position of the triple bond is CH2 = CHCH3 + HBr
indicated by numbering the parent chain from the end that
H2 C CHCH3 + H2 C CHCH3
gives the lowest possible number of the triple bond.
Alkyne names end in -yne: drop the -ane from the alkane H Br Br H
name and add -yne to obtain the alkyne name, as shown
2-bromopropane 1-bromopropane
in the examples (Table 4). (major product) (minor product)
Physical Properties H+
CH2 = CHCH3 + H2 O
Alkenes and alkynes are nonpolar, and their physical +
H2 C CHCH3 H2 C CHCH3
properties are similar to those of alkanes. They have low
melting and boiling points. They do not dissolve in water H OH OH H
or other polar solvents, but are soluble in nonpolar 2-propanol 1-propanol
solvents such as hexane. (major product) (minor product)
1 H on this C H H H H H H Cat.
2 H on this C C C + C C + C C +...
H3 C H H H H H H H H H H
C C + HCl H C C C H H H H H H H
H H H Cl H ... C C C C C C ...
hydrogen goes to this C major product H H H H H H
part of a polyethylene chain
(CH 3CH 2CH 2Cl is produced as a minor product.)
H Ph H Ph H Ph
C C + C C + C C +...
Figure 1. Markovnikov's rule shows how to predict
H H H H H H
the major product of adding an unsymmetrical
reagent to an unsymmetrical alkene. H Ph H Ph H Ph
Cat.
... C C C C C C ...
Oxidation by aqueous KMnO4. Alkenes react with
H H H H H H
strong oxidizing agents such as aqueous KMnO4. The
part of a polystyrene chain
purple permanganate ion is reduced to brown MnO2 in
Ph is the symbol for a phenyl group, C6H5
this reaction, and the alkene is oxidized to a glycol. (A
glycol is a compound that has –OH groups on two
Polyethylene and polystyrene are sometimes written
adjacent carbons.) Note that the following equations are
(–CH2CH2–)n and (–CH2CHPh–)n, respectively. The
not balanced.
group in parentheses is the repeating unit of the polymer.
CH2 = CH2 + KMnO4 H2 C CH2 + MnO 2 Addition reactions of alkynes. Although many
HO OH reactions are possible for alkynes, we will focus on
addition reactions only. Addition reactions of alkynes are
ethylene glycol
(1,2-ethanediol) similar to those of alkenes. Two moles of H2, X2, or HX
can be added across the triple bond so that the products of
CH 3CH = CHCH3 + KMnO4
reaction contain only single bonds.
CH 3CH CHCH3 + MnO 2 H3 C C CH + 2 H2 CH3 CH2 CH3
HO OH
H3 C C CH + 2 X2 CH3 CX2 CHX2
2,3-butanediol
Polymerization. The final important reaction of H3 C C CH + 2 HX CH3CX 2CH 3
alkenes is polymerization. Polymerization is a special major product
kind of addition reaction that involves the linking of When HX is added to an unsymmetrical alkyne, as in
hundreds or thousands of small alkene molecules the example above, three products can be produced. The
(monomers) to each other to form long-chain compounds. one expected in greatest amount is predictable from
That is, the addition that occurs is not between two Markovnikov's rule.
different chemical compounds, but between molecules
that are the same. Note that polymerization of an alkene Problems on Alkenes and Alkynes
converts double bonds to single ones. A catalyst is
1. Give acceptable names (IUPAC or common) for the
required for the reaction.
following compounds.
Polymers are the foundation of the modern plastics
industry. Examples of common polymers include
polyethylene and polystyrene. The production of these
two polymers from their monomers is shown below:
7
H3 C CH 3 H3 C CH 3
(a) C C (b) C C
H H H3 C CH 3
H3 C H H3 C CH 2CH 3
(c) C C (d) C C
H CH 2CH 3 H3 C H
(a) H C C H (b) H3 C C C CH 3
(c) CH 3CH 2 C C H
6. Three products can be produced when HX adds to
propyne. What are they? Give the sequence of reactions
that show how they are formed.
8
AROMATIC HYDROCARBONS
OH
line representation of alternative representation
benzene: each vertex of C6 H6: the circle in the Cl Cl
phenol (an
represents a C-H bond centre represents 3 pairs 1,3-dichlorobenzene
alcohol)
(m-dichlorobenzene)
of delocalized electrons
O
C Cl Cl
The benzene ring is planar, with C-C-C and H-C-C
angles all equal to 120°. The carbon atoms are sp2 H
hybridized. benzaldehyde 1,4-dichlorobenzene
(an aldehyde) (p-dichlorobenzene)
Nomenclature
In disubstituted benzenes, it is still common to use
Systematic nomenclature of aromatic compounds can
the prefixes ortho (o) for 1,2-substitution, meta (m) for
be quite complex, so only a brief guide to nomenclature is
1,3-substitution, and para (p) for 1,4-substitution. See the
included here. Names of a few monosubstituted benzene
dichlorobenzene examples in Table 5.
derivatives are given in Table 5. If there is more than one
substituent, the ring carbons are numbered in sequence so Reactions
that the lowest numbers are obtained for substituents, and
the compound is named as a benzene derivative. For If you know the reactions of the functional groups,
example, you will be able to predict many reactions of compounds
that contain a phenyl group. For example, you would
6
H3 C 5 1 CH 3 expect styrene to add bromine, to be oxidized by
potassium permanganate, and to undergo polymerization
1,2,4,5-tetramethylbenzene
just as do other alkenes—and it does.
H3 C 4 2 CH 3
3
9
ALKYL HALIDES
ALCOHOLS
CH3
The following rules apply to IUPAC nomenclature of tert-butyl 2-methyl-2-
CH3 C OH
alcohols; examples of nomenclature are given in Table 8. alcohol propanol
The longest continuous sequence of carbon atoms to CH3
which the OH group is connected is the basis for the
CH 2 CH 2 ethylene 1,2-ethanediol
parent name of an alcohol. Alcohol names are obtained
glycol
from the alkane name by dropping the final -e and adding OH OH
-ol. The position of the alcohol functional group is
CH 2 CH CH 2
indicated by numbering the parent chain from the end that
glycerine 1,2,3-propanetriol
gives the lowest possible number to the OH group. For OH OH OH
example, the following compound is named as shown
rather than as 2,2-dimethyl-5-heptanol.
Physical Properties
CH 3
The presence of the –OH group in the alcohol makes
H3 C C CH 2 CH 2 CH CH 2 CH 3 the molecule quite polar, since the electronegativities of
CH 3 OH carbon, oxygen, and hydrogen are 2.5, 3.5, and 2.1,
respectively. Alcohol molecles interact with each other as
6,6-dimethyl-3-heptanol
shown in Figure 3. The dashed lines represent the
11
attraction between a partially positively charged hydrogen carboxylic acid combines with the –OH from the alcohol
on one molecule with a partially negatively charged to give water. The R group from the alcohol bonds to the
oxygen atom on a different molecule. This interaction oxygen in the carboxylic acid. This reaction
between two molecules is called a hydrogen bond. It has a is called a condensation reaction because two organic
bond energy of 20 kJ/mol, approximately 5–10% of the molecules “condense” to form the product.
strength of a normal covalent bond. O H+
R – OH + C R'
– R H O
(a) R O
O – O
H
H C R' + H2 O
R joins here
R O
R O Hydrogen bonds ester
–
Two specific examples of esterification are the
–
H
H production of ethyl hexanoate from ethanol and hexanoic
O
acid, and of methyl anthranilate from methanol and
R anthranilic acid. Ethyl hexanoate is one of the dominant
R constituents of a “green apple” flavour, and methyl
O
– anthranilate is the ester that gives native North American
(b)
H grapes their characteristic taste.
– H
O O O
H H+
H H CH3 (CH2 )4 C + CH3 CH2 OH
OH
Hydrogen bonds
O
Figure 3. Alcohol molecules hydrogen bond with each
CH3 (CH2 )4 C + H2O
other (a) and with water (b).
OCH2CH 3
O O
H OH H
C C conc.
CH3 CH2 C C C H
HO O—H HO—CH 2CH 2OH 3 2 1 H2 SO4
H H H
terephthalic acid ethylene glycol
CH3 CH2 CH2 CH = CH2 + CH3 CH2 CH = CHCH3 + H2 O
ester 1-pentene 2-pentene
linkage
O O Oxidation by aqueous KMnO4. The structure type
C C is very important in this reaction. Primary and secondary
O O—CH2 CH2 — alcohols give different products when they react, and
n tertiary alcohols do not react at all with aqueous KMnO4.
The oxidation product of primary alcohols is a carboxylic
acid, whereas secondary alcohols give ketones. Tertiary
repeating unit of the polymer, alcohols do not react because there is no hydrogen
poly(ethyleneterephthalate)
attached to the functional group carbon.
2° alcohol ketone
OH H R"
conc. aqueous
R C C R R2 C = CR2 + H2 O R C OH No reaction
H2 SO 4 KMnO4
R R R'
Double bond between the No H on this C
3° alcohol
carbons that were originally
bonded to the OH and H
Specific examples of KMnO4 oxidations include the
Figure 4. Alcohols split out water to give alkenes when
oxidation of the primary alcohol 1-propanol to propanoic
treated with hot, concentrated sulfuric acid.
acid, and of the secondary alcohol 2-propanol to acetone.
For example, propanol gives propene when it is
aqueous O
heated with sulfuric acid:
CH3 CH2 CH2 OH CH3 CH2 C
H OH H KMnO4
conc. OH
H C C C H CH3 CH = CH2 + H2 O 1-propanol propanoic acid
H2 SO4 H
H H H aqueous O
Some alcohols can give two products when heated H3 C C OH H3 C C
with sulfuric acid, depending on which hydrogen is KMnO4
CH3 CH3
removed. For example, 2-pentanol can give either
1-pentene or 2-pentene, depending on whether a 2-propanol acetone (propanone)
hydrogen is taken from carbon #1 or carbon #3:
13
(a) KMnO4
(b) H2SO4 (with heat applied)
Table 8. Structures and Names of Some Aldehydes concerned with in first year chemistry is the oxidation
and Ketones of aldehydes to carboxylic acids. Ketones are not
oxidized by the normal oxidizing agents.
Structure Common Name IUPAC Name
Aqueous potassium permanganate oxidizes
O
aldehydes quite readily to the corresponding carboxylic
H C formaldehyde methanal
acids. It is easy to tell that a reaction has occurred,
H because the purple
O colour of permanganate ion disappears and a brown
CH 3 C acetaldehyde ethanal precipitate of MnO2 is formed. The general equations
are shown below:
H
O O O
aqueous
CH 3 C propion- propanal R C R C
aldehyde H KMnO4 OH
H
O aldehyde carboxylic acid
CH 3CH 2CH 2 C butyraldehyde butanal
O
H aqueous
R C No reaction
O KMnO4
R
CH 3 CH C iso- 2-methyl-
ketone
H butyraldehyde propanal
CH 3
A specific example is the oxidation of
O benzaldehyde to benzoic acid:
acetone 2-propanone
CH 3 C CH 3 O
O
O aqueous C + MnO2
C
methyl ethyl 2-butanone
CH 3 C CH 2CH 3 H KMnO4 OH
ketone
benzaldehyde benzoic acid
O CH 3 methyl 3-methyl-2-
isopropyl butanone Unfortunately, the test with KMnO4 is not very
CH 3 C CHCH3 specific. KMnO4 is a strong oxidizing agent and reacts
ketone
with alcohols and alkenes as well as with the easily
oxidized aldehydes. However, there is a very mild
oxidizing agent that is used as a specific test for
Physical Properties aldehydes. It is Fehling's solution, and consists of an
Aldehydes and ketones are polar, and hence have aqueous solution of a copper(II) salt. In the reaction,
higher boiling and melting points than nonpolar aldehydes are oxidized to carboxylic acids but alkenes
compounds with similar molecular weights. They cannot and alcohols do not react. Reaction is easy to detect,
undergo hydrogen bonding with each other because there because the blue colour of the copper(II) solution
are no hydrogen atoms with significant partial positive disappears and a red precipitate of Cu2O is produced.
charge; thus they have lower melting and boiling points The following equations show the oxidation of
than the alcohols. propanal to propanoic acid by Fehling's solution, and the
Aldehydes and ketones with five or fewer carbons failure of other classes of organic compounds to react.
are quite soluble in water. The carbonyl group undergoes
O O
hydrogen bonding interactions with the water molecules.
Aldehydes and ketones are also soluble in the usual CH3 CH2 C + Cu2+ CH3 CH2 C + Cu2O
nonpolar organic solvents. H Fehling OH red
solution ppt.
Reactions
Although aldehydes and ketones undergo many
different kinds of reactions, the only one that we are
15
ketones O
alkenes + Cu2+ No reaction (e) CH3 CH2 CH2 C
alcohols CH2 CH2 C(CH3 )3
Fehling
solution 2. Write the organic products of the reactions of the
compounds in Question 1 with potassium permanganate.
The test with Fehling's solution is used in the laboratory If there is no reaction, state NR.
to distinguish between aldehydes and other oxidizable
3. You have an unknown that could be one of the
compounds.
following compounds: 2-methyl-2-propanol, 2-propanol,
propanone, or propanal. Your unknown reacts with
potassium permanganate but not with Fehling's solution.
Problems on Aldehydes and Ketones What is the compound? Explain your reasoning.
1. Name the following compounds. 4. You have an unknown that could be one of the
following compounds: 2-methyl-2-propanol, 2-propanol,
propanone, or propanal. Your unknown reacts with
CARBOXYLIC ACIDS
O O O O
C C
oxalic ethanedioic
CH3 C CH3 C
acid acid
HO OH O O
CH3(CH2)16CO2H stearic octadecanoic
acid acid Salt formation. Carboxylic acids react with bases to
form salts. Examples include the reaction of formic acid
with copper hydroxide to form copper formate, and the
Table 10. Names and Formulas of Carboxylate Anions reaction of acetic acid with ammonia to form ammonium
acetate.
Formula Common Name IUPAC Name
O
HCO2– formate methanoate 2 H C + Cu(OH)2 Cu(HCO2 )2 + 2 H2 O
CH3CO2– acetate ethanoate O H
Physical Properties
Amide formation. Carboxylic acids react with
Carboxylic acids are very polar because of the ammonia or amines in a two-step reaction to produce
presence of both a carbonyl oxygen atom and a hydroxyl amides. In the first step, a carboxylic acid reacts with
group on the same carbon. As a consequence, they form ammonia or an amine to produce a salt. In the second
strong hydrogen bonds to each other as well as to water step, the salt is heated until it splits out water to form the
molecules. Their melting and boiling points are relatively amide. The following reaction shows the steps in the
high, even when compared to other polar organic production of acetamide, CH3CONH2, from acetic acid
compounds such as alcohols that also undergo hydrogen and ammonia. Note that a covalent C–N bond is formed
bonding. in the second step.
Carboxylic acids containing up to approximately five
carbon atoms are water-soluble. Carboxylic acids with
longer carbon chains do not readily dissolve in water, but
dissolve in aqueous NaOH because carboxylate salts are
17
ESTERS
Additional examples of amide formation are given in (b) KOH + CH3(CH 2)16CO 2H
the section on amines.
(c) CH3 CO2 H + CH3NH2
Esterification. The reaction of alcohols with
carboxylic acids to produce esters has been covered
(d) HCO2H + (CH3 )2NH
previously in the section on alcohols.
(e) CH3CH 2CO 2H + NH 3
Problems on Carboxylic Acids
1. Give names of the following carboxylic acids and salts: 4. Suppose that the products of 3(c), 3(d), and 3(e) are
heated. Write structures of the new compounds that will
(a) CH3(CH2)4CO2H (b) CH2FCH2CO2H
be formed.
(c) (CH3)3CCO2H (d) CCl3CO2H
5. Draw the structure of the polyamide that results when
(e) Cu(CH3CO2)2 (f) CaC2O4 H2N(CH2)5CO2H polymerizes.
O
Physical Properties H C
ethyl ethyl
formate methanoate
Esters are polar molecules because of the presence of O CH 2CH 3
two oxygens in the ester functional group, but they
O
H C
n-propyl 1-propyl
formate methanoate
O CH 2CH 2CH 3
cannot undergo hydrogen bonding with each other
because there are no –OH groups. Their physical O
properties are similar to those of aldehydes and ketones.
H C isopropyl 2-propyl
Esters containing up to about five carbons are fairly water
soluble because the oxygens in the ester linkage can O CH CH 3 formate methanoate
participate in hydrogen bonding with water. CH 3
Esters generally have pleasant aromas if they are
O
volatile, and are major constituents of natural fruit
CH 3 C
methyl methyl
flavours.
acetate ethanoate
O CH 3
Reactions
O
Hydrolysis. Hydrolysis literally means “the breaking methyl methyl
apart of water.” In the hydrolysis of an ester, e.g., water is CH 3CH 2 C
propionate propanoate
split apart when the ester reacts to produce a carboxylic O CH 3
acid and an alcohol. The reaction is catalyzed by acids.
The reaction is reversible; at equilibrium there are O
significant amounts of both products and reactants present CH 3CH 2CH 2 C
methyl methyl
in the mixture. The reaction can be forced to the right by butyrate butanoate
O CH 3
using large amounts of water, or by adding base to react
with the acid. CH 3 O methyl methyl 2-
Note that the isopropyl formate ester produces CH 3 CH C isobutyrate methyl-
2-propanol when it is hydrolyzed: O CH 3 propanoate
O
H+
H C CH 3 + H2 O
O CH CH 3 Saponification. Saponification means “soap
making.” Soaps are the sodium or potassium salts of long-
O chain carboxylic acids (12 or more carbons). Soaps are
+ H3 C CH CH 3 made by hydrolyzing a fat (an ester of glycerine) in the
H C
presence of NaOH or KOH; the products are an alcohol
OH OH
and a sodium carboxylate salt (soap).
Common IUPAC
Structure
Name Name
O
H C
methyl methyl
formate methanoate
O CH 3
19
H2 C O C(O)(CH2)16CH 3
HC O C(O)(CH2)16CH 3 + 3 NaOH
H2 C O C(O)(CH2)16CH 3
This is a typical fat –
glyceryl tristearate
H2 C OH
O
HC OH + 3 C (CH2 )16CH3
H2 C OH Na+ - O
Problems on Esters
1. Write structures of the following esters:
(a) isopropyl formate (b) methyl propanoate
(c) n-octyl acetate (d) n-propyl octanoate
O
(b) CH 3CH 2O C
CH 2CH 2CH 3
O
(c) CH 3(CH 2)4 C
OCH3
O
(d) H C
OCH2 CH2 CH2 CH3
AMINES
Structure and Nomenclature Table 13. Structures and Names of Cations Derived by
Alkyl amines are related to ammonia; one or more of Protonating Amines
the hydrogen atoms of ammonia are replaced by alkyl Structure Name
groups. The mono-, di-, and trisubstituted amines are
pyramidal at the nitrogen because of the lone pair of CH3NH3+ methylammonium
electrons. The C-N-C angles are close to the tetrahedral (CH3)2NH2+ dimethylammonium
angle of 109.5°.
(CH3)3NH+ trimethylammonium
N
R"
R
R' N H pyridinium
Amines in which the nitrogen replaces a CH group
in a benzene ring, as in pyridine (Table 12) are planar at
the nitrogen rather than pyramidal. The nitrogen in NH3 anilinium
pyridine is sp2 hybridized, and the C-N-C angle in
pyridine is 120°.
Alkyl amines are named by listing the alkyl groups acid solution because they react to form soluble salts.
and adding -amine. Hence CH3CH2NH2 is ethylamine.
Amines are not pleasant compounds to work with
When amines are protonated, they are named as
because of their intense, unpleasant aromas. Low
derivatives of the ammonium cation (NH4+). Thus
molecular weight alkyl amines such as the methylamines
CH3CH2NH3+ is the ethylammonium cation. Further
have a strong “rotten fish” odor. Other amines smell like
examples of nomenclature are found in Tables 12 and 13.
corpses or worse.
CH3NH2 methylamine H3 C N H + H2 O H3 C N H + OH –
(CH3)2NH dimethylamine H H
+
(CH3)3N trimethylamine
N + H2 O N H + OH –
pyridine
N
Salt formation. Amines react with inorganic and
organic acids to give salts. Again, a proton is transferred
NH2 aniline (phenylamine, from the acid to the lone pair of electrons on the nitrogen.
aminobenzene) Shown following is the reaction of dimethylamine with
21
H H
n O H CH 3
(b)
Nylon - a polyamide C N CH
n
Polyamides also result when amino acids condense (1 monomer)
in biochemical syntheses, in which an enzyme catalyzes
the reaction. The reaction of two amino acids to form a 4. Write equations to show how the following monomers
dipeptide is shown below. Continued reaction of the react to produce polyamides:
dipeptide with more amino acids results in long-chain
(a) HO2CCO2H + H2N(CH2)6NH2
molecules called proteins.
(b) H2NCH2CO2H (this is the amino acid glycine)
22
AMIDES
O R' O R' C N
H
C N C N R H
(b)
R H R H –
Hydrogen bonds O H
Amide nomenclature is based on the name of the
parent acid. The rule is to drop the “-oic acid” ending H
from the IUPAC name, or the “-ic acid” ending from the Figure 4. Amides hydrogen bond with each other (a)
common name, and add "amide.” Thus HCONH2 is and with water molecules (b).
methanamide or formamide. If the amide is derived from
an organic amine, the amine substituents are named and Reactions
their locations are indicated by the prefix N- (to show that
they are bonded to the nitrogen). An example is Hydrolysis. Amides react with water to generate the
parent carboxylic acid and amine (which then combine to
O form the salt). For example, N-methylacetamide
CH 3CH 2 C hydrolyzes to give N-methylammonium acetate:
N CH 3
O
CH 3 CH3 C + H2 O (CH3 NH3+)(CH 3CO 2– )
N,N-dimethylpropanamide NH CH3
First year students will not be required to name amides. Similarly, protein digestion in your stomach involves
hydrolysis to the constituent amino acids:
Physical Properties
R O R O
Amides, especially those containing an N-H group,
are high-melting and high-boiling because of strong H2 N C C N C C + n H2O
hydrogen bonding between adjacent molecules. Note that H H H OH
the hydrogen bond is from the amide hydrogen atom to n
the carbonyl oxygen atom. Many amides are quite soluble R O
in water because of their ability to undergo hydrogen enzyme
n H2 N C C
bonding with water molecules.
H OH
23
SUMMARY PROBLEMS
1. To which class of organic compounds does each of the (a) Suppose that your unknown is water-soluble and tests
following molecules belong? basic with pH paper. Which of the above compounds is
it?
Compound B.p., °C
(b) Suppose that your unknown is not soluble in water but
(a) CH3CO2H 118
does dissolve in carbon tetrachloride. It decolourizes Br2.
(b) CH3CH2CH2NH2 48 What is it?
(c) CH3CH2CH = CH2 -6 (c) Suppose that your unknown dissolves in water but is
(d) CH3CH2CH2OH 97 neither acidic nor basic. It reacts with Fehling's solution.
What is it?
(e) CH3CH2CHO 49
8. You have an unknown that could be one of the
(f) CH3C CCH3 8 following compounds:
(g) CH3C(O)NH2 221 O O
(h) HCO2CH3 32 CH 3CH 2CH 2 C CH 3CH 2CH 2 C
(i) CH3CH2CH2CH3 -1 OH H
O
(j) (CH3)2CO 56
CH 3CH 2 C CH 3
OCH3 CH 3CH 2 CH OH
2. Name each compound in Question 1.
CH 3
3. The compounds in Question 1 all have approximately
the same formula weight. However, their boiling points CH 3CH 2 C OH
are not the same. List the compounds in order of CH 2CH 3
increasing boiling point. Explain the variations in boiling
(a) Suppose that your unknown tests neutral with pH
point in terms of molecular polarity and hydrogen
paper. It reacts with sodium metal but not with aqueous
bonding.
potassium permanganate. Which of the compounds listed
4. Which of the compounds in Question 1 will be soluble above is it?
in water?
(b) Suppose that your unknown tests neutral with pH
5. Which of the molecules in Question 1 can hydrogen- paper. It does not react with sodium metal or with
bond to other molecules of the same compound? aqueous potassium permanganate. What is it?
6. Which of the molecules in Question 1 can undergo (c) Suppose that your unknown tests neutral with pH
hydrogen bonding to water molecules? paper. It does not react with sodium metal, but does react
7. You have an unknown that could be one of the with potassium permanganate and with Fehling's solution.
following compounds: What is it?
(CH3CH2)3N CH3CH2CO2H
CH3(CH2)4CH3 CH3CH2CH2CH2OH
CH3CH2CHO CH3CH2CH2CH2CH = CH2
CLASSES OF ORGANIC COMPOUNDS
H benzoic acid