Concept explainers
(a)
Interpretation:
Suitable nucleophile and alkyl iodide must be identified for the preparation of butan-1-ol.
Concept Introduction :
The SN2 substitution can be used to prepare primary alcohols from primary
(b)
Interpretation:
Suitable combination of alkyl iodide and nucleophile must be identified for the preparation of butyl ethanoate.
Concept Introduction :
The SN2 reaction can be used for for the preparation of ester using sodium salt of
(c)
Interpretation:
The suitable combination of iodoalkane and nucleophile must be identified for the given cyano compound.
Concept Introduction :
The SN2 reaction is characterized by inversion of configuration which is caused due to backside attack of the nucleophile.
(d)
Interpretation:
For the given thiol, proper iodoalkane and nucleophile must be identified.
Concept Introduction:
The SN2 reaction is associated with inversion of configuration. Proper stereochemistry of starting material must be chosen to get the desired stereochemistry of product after inversion of configuration.
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ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
- Rank the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):Rank the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forwardIn the following reaction mechanism, what best describes the role of the Grignard reagent? + CH₂MgBr 1) ether 2) H3O+ The Grignard reagent acts as a nucleophile and attacks the carbonyl carbon. The Grignard reagent acts as an electrophile and is attacked by the oxygen. The Grignard reagent is first protonated by the acid. The Grignard reagent acts as a nucleophile and removes a proton from the methyl group attached to the carbonyl carbon.arrow_forwardClassify each of the following species as a nucleophile or an electrophile:arrow_forward
- Identify the appropriate nucleophile and alkyl halide substrate to prepare this ether: Structure of the alkyl halide substrate? Structure of the nucleophile?arrow_forward2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forwardChoose the reagents suitable for the following transformations.arrow_forward
- Choose the most correct set of reagents for the following reaction.arrow_forwardWhat product is formed when 1-bromopropane reacts with each of the following nucleophiles?arrow_forwardRank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate): Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forward
- Fill in the missing reagents a-e in the following scheme:arrow_forwardThe Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an a-bromo ester with zinc. +ZnBr ОН CH;CH CH,CH,CHCH .C OCH3 CH;CH,CHCH .C OCH3 OCH3 Но CH3CH CH3 ZnBr organozinc reagent ČH3 B-hydroxy ester Describe how each of the following compounds can be prepared, using a Reformatsky reaction: ОН ОН ОН C. ОН .C. a. CH;CH,CH,CHCH b. CH3CH,CHCH CH,CH3 OCH3 с. СН-СH-CH—С ОН d. CH3CH2CCH OCH3 CH3 CH,CH3arrow_forwardWhat is the source of the nucleophilic attack? How does the oxygen get protonated? What causes the elimination reaction?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning