CHEM360 Lab Manual 2009/12 Experiment 11

Experiment 11 Date: 10th June 2018

Student Name: Helen Holy Espedido Student ID:
3330816

Title
Reactions of the common functional groups--Part 2: Alcohols and alkyl halides.

Purpose/Objective of Lab

The basic purpose of this lab is to demonstrate a selection of those reactions

that are typical of two important classes of organic compounds: alcohols and

alkyl halides. In this experiment, a variety of such tests will be performed on a

selection of known compounds. In a later experiment, the student will be

expected to use the same tests plus Infrared and NMR. Several different

tests will be performed on the unknown taken samples of alcohol and alkyl

halides and the observations and interference will be noted and recorded for

the qualitative analysis of the functional group involved in the substance.

Introduction/Theory:

The identification of reactions and characterization of the structures of substances and functional

groups are a vital piece of organic chemistry. Despite the fact that usually conceivable to build

up the structure of a compound on the basis of spectra alone (IR, NMR, and so forth.), the

spectra ordinarily should be supplemented with other data about the compound: elemental

analysis, and corroborative tests for functional groups.

CHEM360 Lab Manual 2009/12 Experiment 11

Reactions of Alcohols

Primary and secondary alcohols can be oxidized by an assortment of reagents, while tertiary

alcohols are not oxidized under ordinary conditions. Contingent upon the conditions and the

reagents utilized, primary alcohols can be oxidized to aldehydes or carboxylic acids. Secondary

alcohols are oxidized to ketones:

The oxidizing agent utilized as a part of this experiment is a mixture of sodium dichromate and

sulfuric acid. On the off chance that a reaction happens, the yellow-orange shade of the oxidizing

agent changes to green, because of the arrangement of chromium(III) ions. At the point when the

reaction can continue by means of the arrangement of a steady carbocation, an alcohol will

respond with a mixture of hydrochloric acid and zinc chloride (known as Lucas reagent) to shape

an alkyl halide.

Reactions of Alkyl Halides

Alkyl halides can respond with nucleophiles by either a SN1 or SN2 mechanism. By concentrate

the conduct of an unknown alkyl halide under conditions that are known to support both of these

two mechanisms, it might be conceivable to make certain deductions in regards to the structure

of the unknown compound. In this experiment, you will utilize known compounds with a specific

end goal to watch how auxiliary variations impact the rate at which a compound reacts in a SN1

or SN2 reaction.

Silver nitrate dissolved in ethanol is a helpful reagent for surveying the reactivity of an alkyl

halide in a SN1 reaction (see Fig. 11.3). The nitrate particle is a poor nucleophile, along these

lines reaction by a SN2 mechanism is probably not going to happen. Also, ethanol is a

reasonably effective ionizing dissolvable and will support reaction by the SN1 course. The

arrangement of an insoluble silver halide likewise serves to upgrade the forward reaction.
CHEM360 Lab Manual 2009/12 Experiment 11

(CH3)2CO is a dissolvable of low extremity, which makes it a helpful dissolvable for SN2

reactions. Iodide particle is an incredible nucleophile, hence if a chemist wishes to think about

the SN2 reactions of an alkyl halide, the reaction of the alkyl halide with potassium (or sodium)

iodide dissolved in CH3)2CO is a decent decision; a.k.a. Finkelstein reaction

General Equations:
CHEM360 Lab Manual 2009/12 Experiment 11

Procedure:
Reference to Lab Manual:
Carmichael, Robert. Browne, Lois. Jaleel, Nyron. Shaw, Lawton. Law, David. Last, Arthur.
2017. CHEM 360 Lab Manual, Athabasca University, Canada, 70-71.
Table 11.1. Table of Reagents for Experiment 11.

Reagent Formula Mwt. Vol/Mass d Mp bp Haz. Properties

1-butanol C4H9OH 74.12 4 drops 0.810 -89.5 117-118 Flamm., Irritant

2-butanol C4H9OH 74.12 4 drops 0.807 100 Flamm., Irritant

2-methyl-2- C4H9OH 74.12 4 drops 0.7887 25.5 82.3 Flamm., Irritant

propanol

Cyclohexanol C6H11OH 100.16 4 drops 0.9624 25.1 161.1 Irritant, Hygroscopic

1-chlorobutane C4H9Cl 92.57 8 drops 0.8862 -123 78.4 Flammable

2-chlorobutane C4H9Cl 92.57 8 drops 0.8732 -131 68.2 Flammable

2-chloro-2- C4H9Cl 92.57 8 drops 0.8420 -25.4 52 Flammable

methylpropane
CHEM360 Lab Manual 2009/12 Experiment 11

1-bromobutane C4H9Br 136.9 8 drops 1.2758 -112 101.6 Flammable, Irritant

2-bromobutane C4H9Br 136.9 8 drops 1.2585 -112 91.2 Flammable, Irritant

Chlorobenzene C6H5Cl 122.4 8 drops 1.1058 -45.6 132 Flammable, Irritant

benzyl chloride C6H5CH2Cl 126.59 8 drops 1.1002 -39 179.3 Toxic, Cancer
susp.agent

3-chloro-1-butene C4H7Cl 90.55 8 drops 0.8978 64-65 Flamm.,

Lachrymator

Bromocylclohexa C6H11Br 163.06 8 drops 1.3359 -56.5 166.2 Flammable, Irritant

ne

Bromocyclopenta C5H9Br 149.04 8 drops 1.3873 136.7 Flammable, Irritant

ne

-bromostyrene C6H5CHCH 183.05 8 drops 1.4269 7 219 Irritant

Br

sodium Na2Cr2O7 261.6 12 mL Toxic, Cancer

dichromate susp.agent

sulfuric acid H2SO4 98.08 Corrosive, Toxic,

Oxidizer

Lucas reagent Solution of ZnCl2 and HCl Toxic, Irritant

zinc chloride, ZnCl2 136.28 2.91 283 732 Corrosive, Toxic

anhydrous
CHEM360 Lab Manual 2009/12 Experiment 11

hydrochloric acid, HCl 36.46 1.20 (110) Corrosive, Highly

conc. toxic

sodium iodide NaI 149.9 Mosit. Sens., Irritant

silver nitrate AgNO3 169.8 Highly toxic,

Oxidizer

nitric acid HNO3 63.01 1.400 Corrosive, Oxidizer

Acetone CH3COCH3 58.09 0.818 56.5 Flammable, Irritant

ethanol CH3CH2OH 46.07 0.785 78.5 Flammable, Poison

CHEM360 Lab Manual 2009/12 Experiment 11
CHEM360 Lab Manual 2009/12 Experiment 11
CHEM360 Lab Manual 2009/12 Experiment 11
CHEM360 Lab Manual 2009/12 Experiment 11

Post Lab Questions:

1. There are four isomeric alcohols having the formula C4H10O, and in this experiment,

you investigated the properties of three of them. How would you expect the fourth

isomer to behave when treated with (i) acidic sodium dichromate, and (ii) Lucas

reagent?

Tertiary alcohols respond promptly with Lucas reagent as confirm by turbidity attributable to the

low solvency of the organic chloride in the aqueous mixture. Secondary alcohols respond inside

five or so minutes. Primary alcohols don't respond obviously with Lucas reagent at room

temperature. Acidic dichromate condition secondary alcohols give ketones and primary alcohols

to carboxylic acids at last Tertiary alcohols gives no reaction

2. On the basis of your results, arrange the eleven halogen-containing compounds in

order of decreasing reactivity in (i) SN1 reactions and (ii) SN2 reactions.

SN1 mechanism

3-chloro-1-butene > 2-chloro-2-methylpropane > 2-bromobutane > bromocyclopentane >

bromocyclohexane > 2- chlorobutane > 1-bromobutane > 1-chlorobutane > chlorobenzene >

beta-bromostyrene

SN2 mechanism

1-bromobutane > 1-chlorobutane > 2-bromobutane > bromocyclopentane > benzyl chloride > 3-

chloro-1-butene
CHEM360 Lab Manual 2009/12 Experiment 11

3. a. What results would you expect to observe when benzyl alcohol, C6H5CH2OH, is

treated with (i) acidic sodium dichromate, and (ii) Lucas reagent?

b. What results would you expect to obtain when 1-chloro-2,2-dimethylpropane is

treated with (i) ethanolic silver nitrate, and (ii) sodium iodide in acetone?

Conclusion:
CHEM360 Lab Manual 2009/12 Experiment 11

In this experiment we have done a few subjective tests that enabled us to recognize functional

groups in organic particles. We have connected what we have realized by portraying organic

compounds as far as their functional gathering and solvency conduct. The functional groups we

have analyzed included alkyl halides and alcohols.

In this experiment we have examined alcohol oxidation by sodium carbonate, Lucas Reagent

Test, Silver nitrate SN1 mechanism and sodium iodide test i.e. SN2 mechanism. This

empowered us to distinguish between primary, secondary and tertiary alcohols. It inspected the

conduct of various alkyl halides and some related compounds under both SN1 and SN2

conditions. Furthermore, how unique compounds responded under various tests.