Lab Final Flashcards

1
Q

What is thin layer chromatography used for?

A

It’s a rapid and inexpensive analytical technique used to separate mixtures.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

Why do compounds in a mixture separate in TLC?

A

Separation occurs because different compounds have different residence times on the stationary phase or mobile phases

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

In TLC, how do polar compounds interact with polar stationary phases?

A

The polar compounds interact with the stationary phase’s polar surface through dipole-dipole attraction and hydrogen bonding

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

In TLC, how do nonpolar compounds interact with polar stationary phases?

A

They don’t. Instead they remain in the mobile phase, and greater movement is observed.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

In TLC, how does the mobile phase move up the plate?

A

Capillary action

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

What two things should you focus on when analyzing TLC plates?

A

1) Appearance of the compound spots

2) Location of the spots

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

Why do compounds move on TLC plates?

A

As the solvent passes over the spot, molecules a that spot location move up the plate differently depending on the polarity and molecular properties of both the molecules and the solvent

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Why is UV light used in TLC plate analysis?

A

UV light can reveal defining characteristics (re: colors) of compounds

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

Why are chemical stains (often inorganic oxidants) used in TLC plate analysis?

A

Stains react with functional groups in the molecule and permit further visualization

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

What is Rf?

A

Ratio to front

Used in place of retention time for TLC chromatography. Defined as the ration of the distance (mm) traveled by a particular component of a mixture to the distance (mm) traveled by the solvent

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

What range do Rf values occur in?

A

0.00 to 1.00

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

What is the purpose of the TLC lab?

A

To perform TLC and analyze the resulting plate to determine the identity of a mixture of compounds in an unknown sample

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

How should you handle the silica gel TLC plate?

A

By its edges only, do not touch the surface!

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

In the TLC lab, what acted as the stationary phase?

A

The polar silica gel plate

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

In the TLC lab, what acted as the mobile phase?

A

The nonpolar solvent

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

In the TLC lab, which was more polar, the stationary phase or the mobile phase?

A

The stationary phase

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

In the TLC lab, which was less polar, the stationary phase or the mobile phase?

A

The mobile phase

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
18
Q

Rf =

A

(distance mobile phase, mm)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
19
Q

What experimental techniques were used in the identification of an unknown aldehyde or ketone (IUAK) lab?

A

Distillation, isolation of a precipitate by vacuum filtration, melting point analysis, and two chemical tests (iodoform and Tollens’)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
20
Q

Why are aldehydes and ketones similar functional groups?

A

They both have carbonyl groups, which allows them to engage in comparable reactions. They also have similar physical properties

21
Q

What are the two functions of distillation in the IUAK lab?

A

1) Helps obtain a pure compounds

2) Provides an important physical attribute of the unknown compound: boiling point range

Bonus: aldehydes tend to contain impurities of their corresponding carboxylic acid, produced by air oxidation. Distillation effectively removes these impurities

22
Q

What does a Tollens’ test assay for?

A

Presence or absence of an aldehyde

23
Q

What does an iodoform test assay for?

A

The presence or absence of a methyl ketone

24
Q

What happens in a Tollens’ test?

A

The aldehyde (should one be present) is oxidized by a silver ion complex [Ag(NH3)2+] into its corresponding carboxylic acid, and the remaining silver(I) salt is reduced to molecular silver and deposited on the vessel in which the reaction was performed.

Silver should deposit as a mirror if the vessel is clean, if the vessel is dirty a colloidal black precipitate is often observed

25
What does a positive Tollens' test indicate?
Presence of an aldehyde
26
Do ketones give positive Tollens' test results?
NO!!!
27
What happens in an iodoform test?
Methyl ketones (should one be present) react with an aqueous hydroxide base and an iodine-derived reagent (potassium triiodide) to give the corresponding carboxylate anion and iodoform (CHI3), which precipitates as a yellow solid
28
What molecules yield positive iodoform test results?
ONLY methyl ketones!!!!
29
What are semicarbazones?
Solid, highly crystalline materials. They're derivatives of imines formed by a condensation reaction between a semicarbazide and either an aldehyde or a ketone. They're used for identifying their parent aldehydes or ketones via melting point analysis
30
What must the semicarbazone product be to accurately determine it's melting point?
Dry
31
What is the purpose of the IUAK lab?
To reinforce experimental techniques previously introduced (distillation, vacuum filtration, mp analysis) and acquire three different pieces of information in order to determine an unknown aldehyde or ketone from a list of known compounds
32
Why was distillation performed first in the IUAK lab?
Because the subsequent chemical tests on the unknown and semicarbazone needed to be performed on the purified distilled product
33
Definition of nucleophilic substitution
A reaction where an incoming nucleophile reacts with an electrophile and replaces a leaving group
34
Hammond's Postulate
States that a transition state most resembles the species closest to it in free energy
35
What does the transition state of an Sn1 rxn most closely resemble?
The forming carbocation
36
What is the purpose of the Sn2+Sn1 lab?
To test a variety of alkyl halides for their abilities to undergo both Sn2 and Sn1 reactions
37
What was used in the Sn2+Sn1 lab to attempt Sn2 rxns?
Sodium iodide with acetone as the solvent
38
What was used in the Sn2+Sn1 lab to attempt Sn1 rxns?
A solution of silver nitrate (AgNO3) in ethanol
39
What indicated a successful Sn2 rxn in the Sn2+Sn1 lab?
Formation of an insoluble precipitate
40
What indicated a successful Sn1 rxn in the Sn2+Sn1 lab?
Formation of an insoluble precipitate
41
What was the purpose of silver nitrate (AgNO3) in the Sn2+Sn1 lab?
To form a white precipitate with the alkyl halide substrates Precipitation confirmed a positive Sn1 reaction
42
Why should the water bath used in the Sn2 portion of the Sn2+Sn1 lab not exceed 50 degrees Celsius?
Because above that temperature the acetone will evaporate or boil out of the open test tube
43
When do reactive halides precipitate in the Sn2+Sn1 lab?
Within 3 minutes at room temp
44
When do moderately reactive halides precipitate in the Sn2+Sn1 lab?
Only when heated
45
When do unreactive halides precipitate in the Sn2+Sn1 lab?
Never
46
With a polar stationary phase, what kinds of molecules have larger Rf values?
Ones that are more nonpolar, less polar
47
In a polar stationary phase, what kinds of molecules have small Rf values?
Ones that are more polar
48
What would happen to a polar compound's Rf if the polarity of the eluent mixture was increased?
Rf would increase
49
You do an mp analysis and the values are off. You suspect this was due to wet crystals. What process or technique other than continued oven drying can help you obtain a more pure sample for your mp analysis?
Recrystallization