Experiment Six - Pre-Lab
.docx
keyboard_arrow_up
School
University of South Carolina *
*We aren’t endorsed by this school
Course
332L
Subject
Chemistry
Date
Feb 20, 2024
Type
docx
Pages
7
Uploaded by AmbassadorRiver1374
Experiment Six – Identification of an Unknown Aldehyde or Ketone
XXXXX
University of South Carolina
CHEM 332L-016
TA: March 14, 2023
Purpose/Objective
The purpose of this lab is to prepare a semicarbazone derivative and a 2,4-
dinitrophenylhydrazone (2,4-DNP) derivative of unknown aldehydes or ketones, recrystallize them, and determine their melting point. Through this process, the identity of the unknown substances can be determined. Introduction
Carbonyl compounds are sp
2
hybridized and trigonal planar with bond angles of 120°. A carbonyl group is relatively uncrowded, but as the alkyl groups around the carbonyl carbon increases, the reactivity of the carbonyl compound decreases. Since oxygen is more electronegative than carbon, oxygen has a greater share of the double bond’s electrons making the carbonyl group polar. Meaning the carbon is an electrophile, electron-deficient, which is subject to a nucleophilic attack. Reactions of carbonyl compounds are mostly acid catalyzed. Through this reaction, the acid will protonate the electronegative oxygen to form a carbocation, which is more susceptible to nucleophilic addition. All reactions are reversible because either of the two atoms with a lone pair attached to the tetrahedral carbon can be protonated and therefore eliminated. The reactions can be acid catalyzed with a controlled pH of 4.5. Derivatives are able to provide a solution by creating a solid for analysis and the solid derivative should be safe, easy to make, has a sharp melting point, and should be stable to hydrolysis. Imines, where the nitrogen atom carries an electronegative group that has a lone pair of electrons, are usually stable. This is due to the electronegative substituent that can participate in the delocalization of the imine double bond. The delocalization decreases the small positive charge on the carbon atom of the imine bond makes it less susceptible to nucleophilic attack. 2,4-
dinitrophenylhydrazine dissolved in EtOH/H
3
PO
4
will form a solid 2,4-dinitrophenylhydrazone when an aldehyde or ketone is reacted with it. Reaction Schemes/Structures
2,4-DNP Semicarbazide hydrochloride Reagents
Name,
Structure,
MW (g/mol)
Melting
°C
Boiling
°C
Density
g/mL
Properties
2,4-DNP
Derivative
(MP)
Semicarb
Derivative
(MP)
Benzaldehyde C
7
H
6
O 106.12
-26
178-
179
1.045
Flammable
liquid; Cherry-
like scent 237 °C
216 °C
3-Heptanone
C
7
H
14
O 114.18
-39
147
0.818
Colorless liquid
with a mild
fruity odor;
slightly soluble
81 °C
101 °C
Acetophenone
C
8
H
8
O 120.15
19.6
202
1.03
Colorless liquid
but solid at
lower
temperatures
238 °C
198 °C
Diethyl ketone
C
5
H
10
O
86.1334
-42
101
0.814
Flammable
liquid 156 °C
138 °C
Cyclohexanon
e
-47
155
0.947
Flammable
liquid oily, white
to slightly
yellow liquid
with a
peppermint-like
162 °C
166 °C
Your preview ends here
Eager to read complete document? Join bartleby learn and gain access to the full version
- Access to all documents
- Unlimited textbook solutions
- 24/7 expert homework help
Related Questions
Importance of melting point in Dehydration Reaction Of
2-Methylcyclohexanol And Phosphoric Acid.
Does it help us predict anything?
arrow_forward
Questions 23 and 24
arrow_forward
help please answer in text form with proper workings and explanation for each and every part and steps with concept and introduction no AI no copy paste remember answer must be in proper format with all working
arrow_forward
This question concerns adrenalin which is a hormone, a chemical messenger which stimulates the central nervous system. It's structure is shown below.
It has a number of functional groups.
What is a functional group?
Identify and name the functional groups.
Give the reagents and reaction conditions that establish the presence of any TWO of the functional groups present in adrenalin
arrow_forward
57/quizzes/secured#lockdown
问题10
5分
Although the yields might be low, what are the reasonable starting materials to achieve this compound?
HCI
A. benzylic acid and 1,5-pentanediol
B. cyclohexanone and 1,4-butanediol
ing
C. cyclohexanone and 1,3-propanediol
D. 1,2-cyclohexanedione and propanol
E. cyclohexanecarboxylic acid and propanol
O A
arrow_forward
WHAT IS THE CHEMICAL EQUATION IN THE PROVIDED TABLE?
arrow_forward
How to get the boiling point using the temperatures on table 1 and how to identify the compound using the melting points on table 2?
Show solution and explanation.
arrow_forward
15. Please help me answer this organic chemistry question
arrow_forward
INSTRUCTIONS: Choose from the options A-E and explain briefly by illustrations the chemistry behind each answer.
arrow_forward
3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in the
presence of a nonnucleophilic base, R,N, involves two successive S,2 reactions and gives
compound A. Propose a structural formula for compound A.
R&N
NH, + Br.
C15H93NO, + 2 R,NH Br
OCH
Br
1-Aminoadamantane
Methyl
2,4-dibromobutanoate
A
arrow_forward
Acylation of Toluene please answer 4-7
arrow_forward
a)
M₂C.
Step 4: c) 1H-NMR analysis of product A
C
D
The hydrolysis of an emide involves the cleavage of the amide bond, which is a carbonyl group (C=0)
bonded to a nitrogen atom. This reaction is typically catalyzed by an acid or a base.
E
Step 3: b)IR analysis of product A:
The broad peaks in the range of 3500 cm³ to 2500cm* indicate O-H stretching frequency of COOH
functional group...
The strong, narrow peak around 1720 cm* indicates C=0 stretching frequency of COOH.
The medium, sharp peak around 1600cm* indicates C-C stretching frequency of benzene ring
Proton A: The small, broad peak around 12 ppm indicates O-H of COOH.
Proton B and proton C: The doublets at 8.1ppm, 7.1ppm indicate di-substituted benzene.
Proton D: The quartet at 2.4 ppm indicate CH₂ unit with adjacent CH₂ unit.
Proton E: Triplet et 1.1 ppm indicate CH₂ unit with adjacent CH₂ unit.
Proton label
relative integration
A
1
B
1
1
2
3
Solution
HH₂O
Heat H₂G.
1600 cm
Product A
chemical shift
12ppm
8.1ppm
7.1ppm
24ppm…
arrow_forward
How do you synthesize Chloramphenicol? Step by step please. (Drug Chemistry)
arrow_forward
Need help with these reaction questions. Include all products please.
arrow_forward
do 2,3,4 please
arrow_forward
PRELABORATORY QUESTIONS
1. Consider the following aldehydes and ketones, which you will study in today's
experiment.
CH3
CH2"
| CHg-Ċ–CH3
CH2-
CH=CH-C-H
-CH2
Cinnamaldehyde
Camphor
CH3O.
.C-H
CH3-C-C-CH3
HO
Varlin
Dlacetyl (2,3-butanedlone)
a. Which of the compounds are aldehydes? Which are ketones?
b. Which of the aldehydes are aliphatic? Which are aromatic?
c. Which compounds would react with Fehling's reagent? With Tollens' reagent? Write
equations for all reactions that occur.
d. Draw the structural formula of an acetal, formed from one of the aldehydes (your
choice), ethyl alcohol, and a trace of acid.
e. Which of the compounds would give a positive iodoform test? Write equations for
reactions that occur.
2. Draw the structure of the functional for a hemiacetal.
group
3. What is evidence for a positive Fehling's test? For a positive Tollens' test?
arrow_forward
KINDLY HELP ME WITH THIS PROBLEM MULTIPLE CHOICE THANK YOU !
arrow_forward
In the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?
arrow_forward
MECHANISM ACTIVITY Base-Induced Ester Hydrolysis (Saponification)
NOC XT
Step 1: Nucleophilic addition of hydroxide ion to the ester carbonyl group
Ahrs MPR R16
H3C.
R
Part A (1 of 2) Draw the curved arrows for Step 1 of this mechanism.
Arrow-pushing Instructions
CH3
H-O:
ÖH
OR'
:Ö
H-O: O: H H
H H
1x xxx
CH3
CH3
Step 1
H3C.
CH3
за
arrow_forward
Select the best answer. Briefly explain the selection. A mechanism is an acceptable explanation.
arrow_forward
1. A student chemist in an attempt to synthesise compound B from the aromatic aldehyde. Use the flow equation to answer I and II .Image attached below
I)Predict the chemical name of compound B
II)What is the reaction name for the chemical transformation of A to B
arrow_forward
Draw a diagram similar to that in figure 6 detailing the separation of 1,2-dichlorobenzene,
phenol (pka = 10), and pyridine by an extraction protocol.
OH
aa
CI
1,2-dichlorobenzene
phenol
·N·.
pyridine
arrow_forward
what is going on in this reaction? How do they reactant work together to produce the final product? How did the reagents work with reaction?
arrow_forward
For this reaction, if 200 g of 4-(4-methylphenyl)benzaldehyde was used to yield a product of 0.180 g. Calculate the theoretical yield, then use the theoretical yield to calculate the percentage yield.
arrow_forward
Which of the following will produce 2-methyl-2-butanol?
1) xs CH3MgBr
I.
2) H20
1) CH3M9B
I.
2) H2O
H2SO4
III.
H20
arrow_forward
II. Choose one test to differentiate the following pairs of compounds from the given tests.
Underline the name of the compound which will yield a positive result.
Qualitative Tests:
Baeyer's test
Ammoniacal silver nitrate test
Combustion test
Beilstein test
Alcoholic silver nitrate test
Compounds
Cyclohexene
Test
benzene
1-butyne
2-butyne
2-methylpentane
2-methylpentene
1-chloropentane
2-chloro-2-methylbutane
arrow_forward
Identify the reagents you would use to convert 1-bromopentane into pentanamide.
1-bromopentane → pentanamide
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary
reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct
solution, provide just one answer.
A. excess NH3
D. H3O+, heat
G. Na₂Cr₂O7, H₂SO4, H₂O
B. NaCN
E. SOCI2
H. 1) LIAIH4; 2) H3O+
C. Mg
F. NaOH
I. PCC or DMP
arrow_forward
Which sequence of steps will give the highest yield of a carboxylic ester product?
Mix 0.1 mole of benzoic acid (C6H5CO2H) with 1.0 mol SOC12, remove unreacted SOC12, then add 0.1 mole of isopropyl alcohol
O Mix 0.1 mole of benzoic acid (C6H5CO2H) with 0.1 mol of NaOH, then add 1.0 mol of isopropyl alcohol and heat, Men remove any unreacted isopropyl alcohol
O Mix 0.1 mole of benzoic acid (C6H5CO2H) with 0.1 mol of NaOH, then add 0.1 mol of isopropyl alcohol and heat
Mix 0.1 mole of methyl benzoate (C6H5-(C=0)-OCH3) with 0.1 mol of isopropyl alcohol and stir overnight
arrow_forward
Can you please give an explanation for question 6 ( continues to 2nd page)? Thank you
arrow_forward
what is going on in this reaction? How do they reactant work together to produce the final product? How did the reagents work with reaction
Provide textual explanation of reaction
Provide clear handwriting and clear image
arrow_forward
Complete the following reactions by supplying the necessary reagents. Type the THREE LETTER CODE only.
@H
*-*
2.
800
3.
H
Choices:
له
المد
5.
6.
AAA HC
BBB. CH³CH₂CH₂MgBr then H*
CCC. CUIR
DDD. Fehling's Reagent
EEE. MeOH
FFF. Heat, HCI
OH
259
-
N-H
مل
cle
7.
8.
B
N=N:
N=N
OH
- -
'OH
GGG. Zn(Hg), concentrated HCI
HHH. KI
III. acidic KMnO4, heat
]]]. SOCI
KKK. LIAIH4, dry EtOH then H*
LLL. MeOH, H+
arrow_forward
SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Related Questions
- Importance of melting point in Dehydration Reaction Of 2-Methylcyclohexanol And Phosphoric Acid. Does it help us predict anything?arrow_forwardQuestions 23 and 24arrow_forwardhelp please answer in text form with proper workings and explanation for each and every part and steps with concept and introduction no AI no copy paste remember answer must be in proper format with all workingarrow_forward
- This question concerns adrenalin which is a hormone, a chemical messenger which stimulates the central nervous system. It's structure is shown below. It has a number of functional groups. What is a functional group? Identify and name the functional groups. Give the reagents and reaction conditions that establish the presence of any TWO of the functional groups present in adrenalinarrow_forward57/quizzes/secured#lockdown 问题10 5分 Although the yields might be low, what are the reasonable starting materials to achieve this compound? HCI A. benzylic acid and 1,5-pentanediol B. cyclohexanone and 1,4-butanediol ing C. cyclohexanone and 1,3-propanediol D. 1,2-cyclohexanedione and propanol E. cyclohexanecarboxylic acid and propanol O Aarrow_forwardWHAT IS THE CHEMICAL EQUATION IN THE PROVIDED TABLE?arrow_forward
- How to get the boiling point using the temperatures on table 1 and how to identify the compound using the melting points on table 2? Show solution and explanation.arrow_forward15. Please help me answer this organic chemistry questionarrow_forwardINSTRUCTIONS: Choose from the options A-E and explain briefly by illustrations the chemistry behind each answer.arrow_forward
- 3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R,N, involves two successive S,2 reactions and gives compound A. Propose a structural formula for compound A. R&N NH, + Br. C15H93NO, + 2 R,NH Br OCH Br 1-Aminoadamantane Methyl 2,4-dibromobutanoate Aarrow_forwardAcylation of Toluene please answer 4-7arrow_forwarda) M₂C. Step 4: c) 1H-NMR analysis of product A C D The hydrolysis of an emide involves the cleavage of the amide bond, which is a carbonyl group (C=0) bonded to a nitrogen atom. This reaction is typically catalyzed by an acid or a base. E Step 3: b)IR analysis of product A: The broad peaks in the range of 3500 cm³ to 2500cm* indicate O-H stretching frequency of COOH functional group... The strong, narrow peak around 1720 cm* indicates C=0 stretching frequency of COOH. The medium, sharp peak around 1600cm* indicates C-C stretching frequency of benzene ring Proton A: The small, broad peak around 12 ppm indicates O-H of COOH. Proton B and proton C: The doublets at 8.1ppm, 7.1ppm indicate di-substituted benzene. Proton D: The quartet at 2.4 ppm indicate CH₂ unit with adjacent CH₂ unit. Proton E: Triplet et 1.1 ppm indicate CH₂ unit with adjacent CH₂ unit. Proton label relative integration A 1 B 1 1 2 3 Solution HH₂O Heat H₂G. 1600 cm Product A chemical shift 12ppm 8.1ppm 7.1ppm 24ppm…arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning