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0 votes
0 answers
40 views

Substitution reaction with alcoholic KOH

Whenever, there is the reagent "alcoholic KOH", we prefer E2 Elimination reaction. However in case of 3 degree alkyl halides, like tert-butyl chloride, why do we not consider SN1 pathway? ...
EagerToLearn's user avatar
0 votes
0 answers
43 views

Secondary alkyl halides and strong base: Sn2 vs E2

I got this question from the PYQs of a college entrance exam. According to the answer key, 4-chloro-3-methylpent-1-ene reacts with NaOH in water to give 4-hydroxy-3-methylpent-1-ene via the SN2 ...
AADETYA JAISWAL's user avatar
2 votes
1 answer
82 views

Difference in reactivity of sodium ethoxide and NaOH in ethanol

What is the difference in the reaction that proceeds when we use the reagent $\ce{C2H5O- Na+}$ and $\ce{NaOH}$ in $\ce{C2H5OH}$ in with, say ethyl chloride. Is the latter considered to be "...
mark's user avatar
  • 201
2 votes
0 answers
85 views

Product of 4-chlorobutan-1-ol treated with KOH in alcohol

I am looking at this problem: I thought the KOH in alcohol would support a nucleophilic attack of hydroxide on the haloalkane, so the product I would get is B (elimination of HCl). However, this ...
DUDE_WITH_J's user avatar
0 votes
1 answer
264 views

Why can't ethoxide ion act as nucleophile?

Consider the reaction of chlorocyclohexane with ethoxide in a suitable inert solvent. The major product according to my textbook is cyclohexene, which implies E2 reaction pathway. Why not SN2? $\ce{...
Leibniz-Z's user avatar
  • 208
2 votes
2 answers
456 views

NaOt-Bu + chloroethane

What is the major product formed by reaction of sodium tert-butoxide and chloroethane? I thought NaOt-Bu is a bulky base and the major product will be ethene due to E2. But the answer says t-butyl ...
Shub's user avatar
  • 408
2 votes
2 answers
606 views

Reactivity of 1-bromo-4-tert-butylcyclohexane isomers with methanol

(1s,4s)-1-bromo-4-tert-butylcyclohexane (1) and (1r,4r)-1-bromo-4-tert-butylcyclohexane (2) are heated (E2) with $\ce{NaOCH3}/\ce{CH3OH}.$ Which isomer will react faster? What will change when $\ce{...
Stormin nn's user avatar
1 vote
0 answers
76 views

Difference between SN' and elimination reactions

My professor has recently taught us about SN' reaction example in which 3-bromo-3-methyl-but-1-ene was reacted with with KCN to yield 4-methyl-pent-3-ene-nitrile as the major product.When I asked him ...
user avatar
2 votes
0 answers
70 views

Why do active methylene compounds give Sn2 reactions?

I dont understand why they are strong nucleophiles when the negative charge is resonance stabilised. Also it is bulky, is there any chance of elimination?
jen's user avatar
  • 21
1 vote
0 answers
38 views

Reaction of aqueous KOH and alcoholic KOH with alkyl halide [duplicate]

CONTEXT: Here's reaction of alkyl halide with aqueous $\ce{KOH}$ and here's the reaction for dehydrohalogenation by alcoholic $\ce{KOH}$ Question Initially $\ce{KOH}$ is aqueous. On reacting with ...
Platyhelminthes's user avatar
6 votes
1 answer
469 views

When does reaction of alcohol with alumina give an ether and when an alkene?

What is the main product when an excess of ethyl alcohol vapour is passed over heated alumina at 250 °C? I read that this reaction gives an ether (here, diethyl ether) at relatively lower temperature ...
Prajwal Tiwari's user avatar
3 votes
1 answer
1k views

Reaction of cyclohexene oxide with LDA

The question given above appeared in the 2016 Indian National Chemistry Olympiad (INChO). What I think is that the epoxide ring is being opened by a base-catalysed mechanism ($\mathrm{S_N2}$). I ...
Shishir Maharana's user avatar
3 votes
1 answer
2k views

Does SN2 favor strong nucleophile and SN1 favor weak nucleophile? Does E2 favor a strong base, and E1 favor a weak base?

I understand if you have a protic solvent, it will stabilize the strong base (to form weak acid) or the strong nucleophile. The protons would react with them. To have an SN2 or an E2, so you need an ...
Consideration's user avatar
3 votes
0 answers
44 views

Why can SN2 reactions occur when the reagents are a primary substrate and a weak nucleophile/base?

The reagents are ethyl bromide and water. In this Khan Academy video at 5:20, the narrator says because ethyl bromide is a primary substrate, the reaction is neither SN1 or E1. This makes sense ...
Consideration's user avatar
0 votes
1 answer
134 views

In the following reaction is E2 or Sn2 favorable?

Question Doubt It is quite obvious that carbonyl compound is going to convert into alkane, but what confuses me is whether Sn2 or E2 will occur at bromide position Although there is heating( which ...
Aditya suresh's user avatar

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