chem 230L dehydration of 2-methylcyclohexanol
.docx
keyboard_arrow_up
School
Chapman University *
*We aren’t endorsed by this school
Course
230L
Subject
Chemistry
Date
Jan 9, 2024
Type
docx
Pages
7
Uploaded by ProfMorningMouse32
CHEM 230L: Organic Chemistry I Lab
Chapman University
Experiment 9: Dehydration 2-Methylcyclohexanol to Form
Methylcyclohexenes
Intended Learning Outcomes
By completing this lab, students will:
Understand the theory of how to use the dehydration of alcohols to generate alkene based compounds.
Learn how to set up a typical acid catalyzed dehydration reaction.
Understand how to analyze basic alkene compounds for the presence of unsaturated carbon-carbon bonds and how to analyze mixtures of isomers via gas chromatography (GC).
Synthesize a mixture of alkenes from the dehydration of 2-methylcyclohexanol and analyze the product(s). Introduction
This week in lab you use one of the reactions you will about in lecture (Dehydration of alcohols)
to synthesize a mixture of 1-methylcyclohexene and 3-methylcyclohexene. As with alkyl halides,
alcohols can undergo elimination reactions to form alkenes. However, the alcohol (hydroxy)
group by itself is a poor leaving group and must be protonated to form water as a good leaving
group. Typically, treatment of an alcohol with acid under heating conditions will allow this
reaction to occur. First, acidic conditions allow for protonation of the hydroxy group to generate a
good leaving group (water) and heat will then promote an elimination reaction (E1 or E2). The
reaction that you will be performing in lab is shown below.
CHEM 230L: Organic Chemistry I Lab
Chapman University
As this reaction is in equilibrium with the reverse acid catalyzed hydration, the desired dehydration can be favored if the desired product is removed during the reaction. Thus, the reaction is performed using a distillation set-up where the desired product is distilled away as it is formed. After the synthesis and isolation of methylcyclohexes, some simple test will be run to look for the presence of alkenes by seeing if bromine and permanganate can perform addition reactions across the double bond in the desired products. Finally, students will try to determine the ratio of the two isomers formed in the reaction by using Gas Chromatography (GC). Pre-Lab Reading
The reading below needs to be completed before the start of lab. 1.
Lecture textbook (Klein, 3
trd
edition): Sections 12.9 (E1 and E2 Reactions with alcohols section only), pages 532-533.
2.
Lecture textbook (Klein, 3
trd
edition): Sections 8.9 (halogenation sections only), pages 373-375.
3.
Lab textbook (Pavia, 6
th
edition): Experiment 24: 4-Methylcyclohexene (introduction only),
page 207.
4.
Carefully read the procedure for the lab experiment below to ensure that you understand the purpose of each step.
Pre-Lab Assignment (15 points)
Answer the following questions:
1.
Draw a reasonable mechanism for the reaction and formation of both products. (5 pts.)
CHEM 230L: Organic Chemistry I Lab
Chapman University
2.
Determine how many moles of 2-methylcyclohexanol (MW = 114.2 g/mol) are used in the
reaction and then determine the theoretical yield for the methylcyclohexene products
(MW = 96.2 g/mol). (5 pts.)
2-methylcyclohexanol (MM = 114.2g/mol; density = 0.93 g/mL) = 5 mL
5 mL * 0.93g/mL = 4.65 g
4.65 g * mol/114.2 g = 4.07*10^-2 mol
96.2g/mol * 4.07*10^-2 mol = 3.92 g of methylcyclohexane products
3.
Draw the product(s) that should form in the unsaturation test using Br
2. Explain why the
disappearance of the orange color of the solution (due to the presence of Br
2 ) is
confirmation that there are unsaturated C-C bonds (alkene or alkynes) present. (5 pts.)
Since bromine has a strong attraction for electrons and can undergo addition reactions with alkenes and alkynes (alkenes in this case), the bromine molecule is added across the double bond. Adding bromine to the unsaturated C-C bonds makes the orange color of the bromine disappear, as the bromine is now part of a new compound. Thus, when we see the disappearance of the orange color, it ensures that unsaturated C-C bonds are present and participating in the stated reaction. Procedure
Safety: Sulfuric acid is corrosive and harmful and causes skin burns/irritation, serious eye
irritation, and respiratory irritation if fumes are inhaled. Wear eye protection, lab coat, and
gloves, and work in a hood at all times. 1. In a pre-weighed graduated cylinder (63.860 g), pour 5 mL 2-methylcyclohexanol (mixture of cis-and trans isomers) and determine the mass of the alcohol. Into a 25-mL round bottomed flask equipped with a stir bar, add the 5 mL of 2-methylcyclohexanol, followed by 3 mL of 9M sulfuric
acid. Gently swirl the flask to thoroughly mix the liquids.
69.039 g – 63.860 g = 5.179 g
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
What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-
butanol?
Loss of a b-hydrogen from the carbocation to form an alkene.
Protonation of the alcohol to form an oxonium ion.
Loss of water from the oxonium ion to form a carbocation.
The simultaneous loss of a B-hydrogen and water from the oxonium ion.
arrow_forward
CH3
CH3
Br-
Br2
.CH3
CH2Cl2
CH3
H3C
H3C
Br
Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an
anhydrous solvent such as CH,Cl,.
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks
the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CH3
CH3
CH3
CH3
H3C
H3C
:Br:
:Br:
arrow_forward
10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look
at the functional group PATTERN present in the molecule, including stereochemistry.
Br
CH3
Br
CH3
arrow_forward
10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look
at the functional group PATTERN present in the molecule, including stereochemistry.
♡
Br
Br
arrow_forward
5.Synthesis. Make the following products from a suitable cyclic alkene starting material.
Look at the functional group PATTERN present in the molecule, including stereochemistry.
Br
CH 3
Br
CH3
arrow_forward
In industrial process, rate of reaction is an important aspect to
enhance productivity. In your opinion, how can a company
enhance production of alkene from alkyl halide?
H20
`CI
3-methylbut-1-ene
1-chloro-3-methylbutane
I. Increase concentration of water
II. Increase concentration of 1-chloro-3-methylbutane
III. Use 1-iodo-3-methylbutane instead
IV. Use 1-fluoro-3-methybutane instead
O a. Il and IV
O b. I and IV
O c. I, II, and III
O d. I, Il and IV
e. Il and III
arrow_forward
1.
Write the structure of the major organic product for reactions a, b and e?
H₂C
b. H₂c-
CH,
CH₂
Cold KMnO,
OH
A KMnO,
H
c. CH3CH₂-CH=CH-CH₂CH3 + H₂SO4 →
arrow_forward
Hi! I am working on some Organic Chemistry homework and one of the questions asked what would happen if Butanol was used as a solvent instead of water when mixed with methanol,ethanol, and hexan-1-ol
arrow_forward
help me please
Please fill in the reagents,intermediates, and/or products of the following reactions.
all the reactions shall be covered in Chapter 12-15 from Organic Chemistry, 6th Edition by Marc Loudon and Jim Parise.
arrow_forward
Question 13 of 28
Fill in the blanks:
Professor Lolita Carbon has assigned the analysis of unknown hydrocarbon samples to Enteng Mabutingting based on their reaction profile. The summary of the observed reactions are tabulated below along with the possible structures of the
samples. Identify each unknown sample by matching the respective reaction profile with the given structures. Name each structure.
Sample
1
2
3
H3C.
H3C
Br₂ in CCl4 (dark)
Fading of reddish-brown
color
Fading of reddish-brown
CH3
No reaction
1
A
Complete the table below.
Sample
2
color
3
CH3
Br₂ in CCl4 (light)
Fading of reddish-
brown color
Fading of reddish-
brown color
Fading of reddish-
brown color
H₂C
B
B
Compound (Letters
only)
C
CH3
5-diyne
KMnO4 in NaOH
No reaction
Brown precipitates
Brown precipitates
H₂C
C
AgNO3 in NH3
No reaction
No reaction
Silver precipitates
CH3
Name
1-ethyl cycloh
hexa-1
A
arrow_forward
orgo chem questions
arrow_forward
4. Show the steps and reagents needed to transform 1-propyne into 2-methylheptane.
You may use any alkyl halide and inorganic reagents.
1-propyne →
2-methylheptane
arrow_forward
Can you explain it? Provide examples with the various steps and explanations. How halogens affect the boiling/melting point? Does number of halogens affect it? For example, Ch3-Ch3 vs Ch3-Br vs Br-Ch3-Br
arrow_forward
Bn
Draw the structure of the major organic product formed from the reaction below.
Bn
H
ད ་
+
HỌỌC.
NH2
N
DCC
....
NH
H
Bn
arrow_forward
5.Synthesis. Make the following products from a suitable cyclic alkene starting material.
Look at the functional group PATTERN present in the molecule, including stereochemistry.
Br
Br
arrow_forward
The pictured reaction shows an alkyl bromide being converted into an alkene.
Choose all reagents that would produce the pictured alkene as the major product.
A) NaOH/H2O
B) H2O
C) tBuOK/tBuOH
D) EtONa/EtOH
arrow_forward
Can this alcohol be synthesized selectively by hydroboration-oxidation of an alkene?
arrow_forward
Chemistry
Draw the structure of the missing reactants intermediate or products in the following mechanism. will rate.
arrow_forward
1. The acid-catalyzed elimination of an alcohol is an equilibrium reaction and requires special reac-
tion conditions to favour the formation of the alkene product. What chemical principle controls the
amount of alkene product that is produced? Provide two laboratory techniques that can be used to
obtain good alkene yields in alcohol elimination reactions.
arrow_forward
1.
Predict the product(s) and propose a mechanism of the
following nucleophilic substitution reaction. Remember that a
mechanism should contain arrows to show movement of
electrons, all intermediates and appropriate formal charges.
Br
+ H₂O →
arrow_forward
HW 10# 1
I need help with the last part (Part 3)
arrow_forward
The conversion of alcohols into alkyl halides by reaction with hydrogen halides is an example of a Nucleophilic Substitution Reaction. This kind of reaction can proceed by two different mechanisms depending on the structure of alcohol substrates used. Generally, primary alcohols are substituted via SN2 mechanism, while secondary and tertiary alcohols undergo SN1 mechanism.
Consider the following reaction given in the picture below and the questions in the picture too.
arrow_forward
Select the correct statements regarding the reactions of tertiary haloalkanes. *
A- Tertiary haloalkanes form alkenes through both the E1 mechanism and the E2 mechanism.
B- Tertiary haloalkanes react with water to form ethers.
C- A tertiary haloalkane always forms a tertiary carbocation as an intermediate when a substitution reaction occurs.
D- A tertiary haloalkane always forms a tertiary carbocation as an intermediate when an elimination reaction occurs.
arrow_forward
Predict the major products of both organic reactions.
Be sure to use wedge and dash bonds to show the stereochemistry of the products when it's important, for example to distinguish
between two different major products.
+
X
H₂O
Click and drag to start
drawing a structure.
+
©
A
B
1. Hg (OAc)2, H₂O
Click and drag to start
drawing a structure.
2. NaBH4
arrow_forward
Consider the reaction of 2-bromo-2-methylpropane with water, shown below, to answer the following
question(s).
CH3
H₂C-C-Br
CH₂
H₂C-
CH3
Diagram 1: The first step of this reaction is shown below.
CH3
CH3
1
H₂C-C-Br
H₂C C +
T
CH3
a.
CH3
B
Diagram 2: The second and third steps of the reaction are shown below.
CH₂
CH
CH₂
b.
C.
H₂O
CH₂
d.
10
CH3
H₂C-C-OH +
H
H
HC C
a rearrangement reaction.
an elimination reaction.
an addition reaction.
CH₂
H
Br
1
HBr
1) Refer to Diagram 1 and 2. This reaction is an example of:
a substitution reaction.
ÖH₂
H₂C-C-
CH₂
H
+ H₂O*
arrow_forward
Provide the major substitution product for the following reaction.
arrow_forward
Acyl transfer (nucleophilic substitution at carbonyl)
reactions proceed in two stages via a "tetrahedral
intermediate." Draw the tetrahedral intermediate as it is
first formed in the following reaction.
CI
H₂N
OH
• You do not have to consider stereochemistry.
• Include all valence lone pairs in your answer.
• Do not include counter-ions, e.g., Na+, I, in your
answer.
• In cases where there is more than one answer,
just draw one.
Sn [F
arrow_forward
HO-A-OH
HO-C-B-C-OH
ethylene glycol
(A group)
terephthalic acid
(B group)
The starting materials fer this reaction are ethylene glycol and terephthalic acid. The letters A and B represent organic groups that are unreactive.
What reactive organic functional group does ethylene glycol (containing the A functional group) contain? Enter its name.
Recheck
Next
(1 of 7)
2nd attempt
arrow_forward
Use the following reagent table for the reaction of :
cyclohexanol + H2 SO4 → cyclohexene
Chemical
MW (g/mol) Density (g/mL) mmols used
Amount used
cyclohexanol
100.16
0.9624
1.50 mL
Sulfuric Acid
98.08
1.83
1.0 mL
cyclohexene
82.14
How many mmols of sulfuric acid are used? (answer with 2 decimal places, no units)
arrow_forward
Hydroboration of Alkenes vs. Alkynes. Addition of an alkylboranes to a carbon- carbon double
bond ("hydroboration") followed by oxidation is a common way to alcohols, for example,
addition of dimethylborane to 2,3-dimethyl-2-butene yields 2,3-dimethyl-2-butanol.
Me₂BH + Me₂C=CMe₂- →→ Me₂CH-CMe₂OH
The reaction is more general as borane also adds to carbon-carbon triple bonds. obtain structures
and energies for reactants and transition states for addition of dimethylborane (Me₂BH) to both
ethylene and acetylene. Which reaction has the lower activation energy? Offer an explanation for
your result.
arrow_forward
7:51 PM Sun Oct 16
←
Question 9 of 15
HO
Curved arrows are used to illustrate the flow of electrons. Follow the curved arrows
and draw the hydrocarbon product of the following reaction. Include all lone pairs and
charges as appropriate. Ignore inorganic byproducts.
H3C.
CH3
CH3
@ 100%
Select to Draw
Submit
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
- What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2- butanol? Loss of a b-hydrogen from the carbocation to form an alkene. Protonation of the alcohol to form an oxonium ion. Loss of water from the oxonium ion to form a carbocation. The simultaneous loss of a B-hydrogen and water from the oxonium ion.arrow_forwardCH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forward10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH3 Br CH3arrow_forward
- 10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. ♡ Br Brarrow_forward5.Synthesis. Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH 3 Br CH3arrow_forwardIn industrial process, rate of reaction is an important aspect to enhance productivity. In your opinion, how can a company enhance production of alkene from alkyl halide? H20 `CI 3-methylbut-1-ene 1-chloro-3-methylbutane I. Increase concentration of water II. Increase concentration of 1-chloro-3-methylbutane III. Use 1-iodo-3-methylbutane instead IV. Use 1-fluoro-3-methybutane instead O a. Il and IV O b. I and IV O c. I, II, and III O d. I, Il and IV e. Il and IIIarrow_forward
- 1. Write the structure of the major organic product for reactions a, b and e? H₂C b. H₂c- CH, CH₂ Cold KMnO, OH A KMnO, H c. CH3CH₂-CH=CH-CH₂CH3 + H₂SO4 →arrow_forwardHi! I am working on some Organic Chemistry homework and one of the questions asked what would happen if Butanol was used as a solvent instead of water when mixed with methanol,ethanol, and hexan-1-olarrow_forwardhelp me please Please fill in the reagents,intermediates, and/or products of the following reactions. all the reactions shall be covered in Chapter 12-15 from Organic Chemistry, 6th Edition by Marc Loudon and Jim Parise.arrow_forward
- Question 13 of 28 Fill in the blanks: Professor Lolita Carbon has assigned the analysis of unknown hydrocarbon samples to Enteng Mabutingting based on their reaction profile. The summary of the observed reactions are tabulated below along with the possible structures of the samples. Identify each unknown sample by matching the respective reaction profile with the given structures. Name each structure. Sample 1 2 3 H3C. H3C Br₂ in CCl4 (dark) Fading of reddish-brown color Fading of reddish-brown CH3 No reaction 1 A Complete the table below. Sample 2 color 3 CH3 Br₂ in CCl4 (light) Fading of reddish- brown color Fading of reddish- brown color Fading of reddish- brown color H₂C B B Compound (Letters only) C CH3 5-diyne KMnO4 in NaOH No reaction Brown precipitates Brown precipitates H₂C C AgNO3 in NH3 No reaction No reaction Silver precipitates CH3 Name 1-ethyl cycloh hexa-1 Aarrow_forwardorgo chem questionsarrow_forward4. Show the steps and reagents needed to transform 1-propyne into 2-methylheptane. You may use any alkyl halide and inorganic reagents. 1-propyne → 2-methylheptanearrow_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