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Richard A. Kjonaas
Indiana State University, Terre Haute, IN 47809
Bernie A. Riedford
Mt. Vernon Senior High School, Mt. Vernon, IN 47620
Test Time.'Minutes
Boiling Order of Drops of Alcohol (TempraNre.OC)
Alcohol Point, "C Additionb l(20 'C) l(25 ' C ) 2(25 OC) 3(25 'C) q25 ' C ) Cost.Q/g
A to R -L 15
R to A 20
AtoR 3.0 1.0
R to A 1.0
A to R 0.5 0.25
RtoA 0.25
A to R 0.5 0.25
R to A 0.3
A to R 1.3 0.5
R to A 0.75
A to R 0.25 0.1
R to A 0.1
AIoR 0.2 0.1
R to A 0.1
AIoR 1.3 0.5
RIoA 0.7
A to R 0.2 0.2
RtoA 0.2
AtoR 0.25 0.2
R to A 0.3
A to R 1 0.5
R to A 0.5
AtoR 0.25 0.15
R to A 0.15
-
'Ign~ring~ t e r B O i m r i S m .
'"A tow means mat the alcohol was added to ma reagent: "R M A" means that the reagent was added to the alcohol.
<mgamount of time between me initial addition and the first appearance of a definite cloudinem.
M the best 1990 orics in ousntities of 2 ka or less of at least 97% owe matwial.
Table 2 eives the 2' alcohol test times that were obtained In light of all this, one can easily see some reasons why the
by alteringthree variables: temperaure, reagentlalcohol vol- test so often fails with 2- alcohols. For example, some stu-
ume ratio, and order of addition. The data shows that (1) a 5 dents might use "a little extra" alcohol thinking that, if
OC drop in temperature can give as much as a threefold anything, this should cause the test to work better! Some
increase in the test time, (2) using more alcohol per given instructors may want to caution students about this and
amount of reagent leads to longer test times, and (3) thk test about additional swirling; others may choose rn let the stu-
times are often longer when the reagent is added to the dentv pay the consequences of not followingdirections. Even
alcohol rather than when the alcohol is added to the reagent. if the students do follow the directions, some lab manuals
A fourth variable that affects the test times but that is not provide procedures that, because of the reagentlalcohol vol-
reflected in the table is the extent of mixing. No matter what ume ratio, are likely to fail or, in some cases, certain t o fail.
the order of addition, extensive mixing can lead to longer Also, students might be using larger than desired amounts of
test times. As would he expected then, swirling a just barely alcohol simnlv because some medicine dronoers deliver lare-
cloudy test mixture will, in some cases, cause i t to clear up er drops t h k o t h e r s . The instructor can &imize the nu;-
and then..uDon sittine.
& -.become cloudvaeain.
- -
For consistencv
in this study, the test mixtures weremixed by swirlingvigor-
her of failed tests bv havine the students use a Lucas test
procedure that giveaveryshGrt test times and then by citing
ouslv for about 3 to 5 s and were then olaced in a test tube an expected test time that is long enough to accommodate
rack and allowed to sit until cloudy. A little more initial
swirline. such as 10 to 15 s. usually has verv little effect on The reaaentlalmhol
. .- - - - ratio
~ .effect
. -~-~ and the temaereture
- effect were-
-~~ -
the tesitimes; i t is additional swiriing sometime during the
~ ~~
~
7 - ~ ~~ ~
mixing effect. However, that would not explain the observation that
- the
due to the ability of the alcohol to dissolve the alkyl chloride when 4 drops of 3.3dlmethyl-2-butanol are added to 10 drops of
as i t forms. In fact, a cloudy test mixturecan often becleared reagent followed by continuous and vigorous swirling until cloudy, the
up by adding another drop or twoof the alcohol being tested. testtime is increased tooniy about 3 min ratherthan to 8 min, which is
The reasons for the order of addition effect and the mixing the test time that is obtained when 10 drops of reagent are added to 4
effect are not as easy to e ~ p l a i n . ~ drops of the alcohol with 3 to 5 s of mixing.
best if freshlv oreoared". The tendency of Lucas reagent to and, by streaming to the surface of the very dense Lucas
lose its reactivity Is perhaps due to both the loss of H C and
~ reagent, gives a momentary illusion of a positive test. The
the uotake of water from the air. When 100 mL of freshly real cloudiness, alkyl chloride formation, appears later-all
prepa.red reagent was allowed tosit in an open 1-Lbeaker f i r the more reason to use a high reagent/alcohol ratio.
24 h, the volume of the reagent increased to 115 mL, and the
time required for it to gives positive test with 2-butanol (1 Summan and Conclusion
drop added to 10 drops of reagent) increased by a factor of With a little awareness and cautioll on the part of both the
40. b n the other hand, when 160 mL of reagent was stored in lab instrudor and the students, the Lucas test can be very
a stoppered 250-mL bottle with occasional use for 7 months, reliable. Resisting the urge to use a little extra alcohol is
the test time with 2-butanol increased by less than 50%. es~eciallv. im~ortant.
. The data in Tables 1 and 2 should be
Another batch was made from concentrated HCl that had useful to the lab instructor when (1) developing a list of
been stored for several months in a typical mineral acid unknowns, (2) deciding whether a particular batch of Lucas
reagent bottle with a glass stopper; the resulting test times reagent is reliable enough for the students to use, (3) choos-
were more than twice as long as those obtained when a fresh ing a procedure for the students to use, and (4) describing to
bottle of HC1 was used to make the reagent. The data in the students the expected results when 2 O alcohols are sub-
Table 2 can be used a s a measuring stick to check the jected to the Lucas test. One can reliably expect 2' alcohols
quality of a bottle of reagent. to give a positive test within about 5 s to 5 min when adding 1
We have also examined the confirmatory test for 3' alco- drop of alcohol to 10drops of reagent. Isopropyl alcohol is an
hols. The five 3O alcohols in Table 1do indeed react quickly exceotion. There is orobablv no need to include the concen-
(within a minute) with concentrated HCl whereas the 2' tra&d HC1 step (the confirmation of 3' alcohols), especially
alcohols do not. At least for the limited number of alcohols if the list of unknowns includes onlv those alcohols used in
used for this study, there appears to be no need for this this study.
confirmation since even the shortest 2' alcohol test time Althoueh a comolete list (or rule for eeneratine a list) of all
withLucas reagent ( 5 4 s) is clearly distinguishable from the alcohols chat are soluble &the ~ u c a b e a g e nGill
t does not
instantaneous result that is characteristic of the 3" alcohols. exist and orobablv never will, students can at least be told
Furthermore, when using concentrated HC1 instead of the that all C ; H ~ , + ~ OC.~6 alcohols are soluble.
Lucas reagent, the "cloudiness" is not easy t o recognize. I t
quickly turns to larger droplets or to a difficult-to-see layer
of alkylchloride. Of the five 3' alcohols used in this study, 3-
methyl-3-pentanol is by far the trickiest when doing the - -
-
Finally, any alcohol that is insoluble in the reagent might Laboratom 2nd ed.: Wllev: New York. 1989: D 41 1.
aooear to be eivine a oositive 3O test. For this reason, it is ato on; 'D. C. Liboriixy lnvesii&tions 'in organic Chemistry;
important forihe &dent to know in advance which alc&ols McGraw-Hill: New York. 1989; p 736.