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SN1 vs SN2 Reaction Mechanisms

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0% found this document useful (0 votes)
17 views5 pages

SN1 vs SN2 Reaction Mechanisms

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periwinklemohite
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
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VEERMATA JIJABAI TECHNOLOGICAL INSTITUTE MUMBAI

(An Autonomous Institute affiliated to University of Mumbai)

H R Mahajani Marg, Matunga east, Mumbai, Maharashtra- 400019

Examination: Assignment-1 Date of submission: 24-10-2024


Semester and Program: F. Y. [Link], SEM-I Time allowed: 1 Hr.
Branch: Electronic Engineering Course: Engineering Chemistry-I (R5CH1011T)

Instructions (1) Attempt all questions


(2) Illustrate your answers with neat sketches wherever necessary.
{Atomic weights: H=1, C=12, N=14, O=16, S=32, P=31, Ba = 137, Cl=35.5}.
(3) latent heat of vapourization is 540 Cal/g
Q.1 A. 6M CO1
Write SN1 reaction mechanism with an energy profile diagram. (3+1M)
Consult any text book of organic chemistry/ class notes. Plz provide specific examples of
t
Butyl chloride.

Name two factors affecting SN1 and SN2 reactions. 2M (0.5M X 4 points)

For SN1 : a) stability of carbocation: 3° >2° > 1° , compounds having possibility of


generation of 3° carbocation will respond in faster rate compared to others.
b) polar protic solvents prefer this type of reaction as it provide better stability to
carbocation generated in 1st step.
c) nature of leaving group : size mismatch with Carbon so C-X bond become weaker and
the order is I > Br > Cl >F

For SN2 : a) nature of substrate: primary halides having less steric crowding respond to
this reaction at faster rate.
b) protic solvents (those, such as water or alcohols, with hydrogen-bond donating
capability) decreases the power of the nucleophile through strong solvation. If Nu is
not free who will attack? But polar aprotic solvents (e.g. acetone, DMF) lack
hydrogen to make H-bonding with Nu, so it remains free to attack the substrate.

B. Write down the reaction scheme for chalcone synthesis. 2M 4M


Only reactants, reagents and the proper product, donot go for -NO2 derivative if not
asked… I know you!
What is heterolytic and homolytic fission. Give examples. 2M
Give 2 specific examples. Homo: Cl – Cl 2C
֗ l
Hetero – HCl H+ + Cl-

Q.2 A. C=90%, H = 4%, O=3%, S = 0.8 %, and ash=2.2%. Calculate HCV and LCV of the fuel. 6M CO2

Dulong’s formula, 𝐻𝐶𝑉 = [ 8080 𝐶 + 34,500 (𝐻 − ) + 2240 S]


𝐻𝐶𝑉 = [ 8080 𝑋 90 + 34,500 (4 − ) + 2240 X 0.8]
HCV = 8540.55 Kcal/kg

LCV = HCV - 0.09 H X 540 Kcal/Kg = 8540.55 – 0.09 X 4 X 540 kcal / Kg


= 8346.15 Kcal/kg
If a coal sample contains carbon, moisture, nitrogen, sulfur and ash, find out a
mathematical expression to calculate hydrogen available for combustion.

B. Why GCV > NCV ? 2M 4M


Reaction of steam formation 1M, explanation 1M

GCV = NCV + latent heat of vaporization


Mention the parameters which are responsible for ranking of coal. 1M
Result of proximate analysis, %M, % VM, % ash and %fixed carbon. Write if % more
rank is less, for Fixed carbon if % is more rank is good, one line per parameter will be
enough.
Mention the calorific value of most matured coal. 1M
Anthracite, calorific value = 8650-8700 Kcal/Kg [follow book values only]
Q.3 A. 0.85g of Naphthalene was analyzed in the Bomb Calorimeter. The weight of the water 6M CO2
taken in the bomb was 2500 g, water equivalent was observed 650g. Rise in temperature
observed was 2.50C. The fuse wire correction was 10 Cal. Acid correction observed was
50 cal. Calculate the cooling correction of the System. GCV of the sample is 9305.29
Cal/g.

Write down the balanced reactions of acid corrections.

B. 2.21 g coal after heating for 1 hr at 110°C the residue weighed 1.93 g. The crucible 4M CO2
covered with a vented lid and strongly heated for 7 mins at 950°C. The residue weighed
1.228 g. The crucible was heated without cover at 750°C, until constant weight was
obtained. The weight of last residue was 0.245 g. Calculate the % results of the above
analysis.
Ans: %M = 12.67
%VM = 31.76
%Ash = 11.086
% Fixed Carbon = 44.49
Arrange above parameters in increasing order of their importance for a good fuel. 0.5M
% Fixed carbon > % Volatile Matter > % Moisture > % Ash content

Q.4 A. Ethanol synthesis by fermentation of glucose, 6M CO6

Comment whether above reaction is green and identify principle(s) of green chemistry that
was/were followed/violated.
To comment whether its green or not calculate %AE.
Step 1: balance the reaction
Step 2: molecular weight of individual components.
Step 3: write the formula
Step 4: calculate the answer

2M for calculation of %AE, 2M for writing general statements of the green chemistry
principle.
Principles involved: #2, #7, #6, #10
How adipic acid synthesis by green synthetic route achieved sustainability. 2M

Adipic Acid

In green synthesis of adipic acid, starting material is glucose which is a renewable


feedstock and [Link] is used as catalyst.

B. Write two importance of sustainability in modern life? 2M 4M


notes
State the green chemistry principle(s) that is(are) followed/violated in following cases.
a) Use of supercritical CO2 in medical sterilization instead of ethylene oxide. #5
b) Photocatalytic hydrogen production from pure water. #9, #7, #6
Depending on the marks write GENERAL STATEMENT OF THE PRINCIPLE.
Check marks if two marks are there, atleast write 2 principles among others (if
any).

------XOX----

Common questions

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Coal ranking is based on proximate analysis, including the percentage of moisture, volatile matter, ash, and fixed carbon content. A lower percentage of moisture and ash results in higher quality coal, as they reduce energy content and efficiency. Higher volatile matter may indicate lower rank, while higher fixed carbon percentage indicates better quality and energy efficiency .

Chalcone synthesis involves the Claisen-Schmidt condensation reaction between an aromatic aldehyde and an acetophenone in the presence of a base, typically NaOH or KOH, to form the α,β-unsaturated ketone product known as chalcone. The specific steps include deprotonation of acetophenone by the base, followed by nucleophilic attack on the aldehyde, leading to an aldol intermediate which dehydrates to yield chalcone .

Given 0.85g of naphthalene with a water mass of 2500g and water equivalent of 650g in the bomb calorimeter, with a temperature rise of 2.50°C, and corrections of 10 Cal (fuse) and 50 Cal (acid), the energy output is calculated. The formula is GCV = (water mass + water equivalent) * temperature rise + corrections. Therefore, GCV = (2500g + 650g) * 2.50°C + 60 Cal, confirming the sample GCV as 9305.29 Cal/g .

An SN1 reaction with tert-butyl chloride involves a two-step mechanism. In the first step, the tert-butyl chloride undergoes heterolytic cleavage, forming a tert-butyl carbocation and a chloride ion. The energy profile of this step shows an endothermic peak corresponding to the activation energy required to form the carbocation. In the second step, the carbocation reacts with a nucleophile to form the final product, which is exothermic. Factors affecting the reaction include the stability of the carbocation (3° > 2° > 1°), the use of polar protic solvents which stabilize carbocations, and the nature of the leaving group (I > Br > Cl > F).

The higher calorific value (HCV) of a fuel is calculated using the formula: HCV = (8080 * %C + 34,500 * (%H - %O/8) + 2240 * %S) / 100. The lower calorific value (LCV) is obtained by subtracting the latent heat of vaporization of water from HCV, i.e., LCV = HCV - 0.09 * %H * latent heat . Applying these to the values C=90%, H=4%, O=3%, S=0.8%, the calculated HCV is 8540.55 Kcal/kg and LCV is 8346.15 Kcal/kg .

The gross calorific value (GCV) is higher than the net calorific value (NCV) because GCV includes the latent heat of vaporization of water produced during combustion. The reaction involved is the formation of steam (H2O(g)), which requires energy input for vaporization. Hence, NCV is obtained by subtracting the latent heat of vaporization from the GCV, demonstrating why NCV is lower .

Homolytic fission occurs when a bond breaks evenly, with each atom retaining one of the shared electrons, forming two radicals. An example is the homolytic fission of a Cl-Cl bond, producing two Cl radicals. Heterolytic fission involves the uneven breaking of a bond, where one atom takes both electrons, forming a cation and an anion. An example is the heterolytic fission of HCl, forming H+ and Cl- ions .

Supercritical CO2 is considered a greener alternative for sterilization as it adheres to green chemistry principles, such as reducing toxicity (Principle #5). It replaces ethylene oxide, a traditional sterilant known for its toxic and explosive properties, thus enhancing safety while maintaining efficacy in sterilizing medical equipment .

Ethanol synthesis by glucose fermentation can be considered green based on the percentage atom economy (%AE) that utilizes renewable resources efficiently. Principles adhered to include using renewable feedstock (Principle #7) and safer solvents (Principle #2), while possibly violating the principle of efficient energy use (Principle #6). The calculated %AE helps assess adherence more precisely, ensuring the reaction uses materials efficiently with minimal waste .

For SN1 reactions, the main factors include the stability of the carbocation (tertiary carbocations are more stable), and the use of polar protic solvents which stabilize the carbocation formed in the first step. For SN2 reactions, factors include the nature of the substrate (less steric hindrance in primary halides), and the use of polar aprotic solvents which do not solvate the nucleophile, allowing it to attack the substrate freely .

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