(a)
Interpretation: An efficient synthesis for the given transformations has to be proposed.
Concept Introduction:
Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on
Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.
A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.
To find: Propose an efficient synthesis for the given transformation (a)
Decide the transformation
(b)
Interpretation: An efficient synthesis for the given transformations has to be proposed.
Concept Introduction:
Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.
- 1) Generation of an electrophile
- 2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.
- 3) Deprotonation of the arenium ion by a weak base to regain aromaticity.
Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.
A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.
To find: Propose an efficient synthesis for the given transformation (b)
Apply a retrosynthetic analysis
(c)
Interpretation: An efficient synthesis for the given transformations has to be proposed.
Concept Introduction:
Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.
A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.
To find: Propose an efficient synthesis for the given transformation (c)
Apply a retrosynthetic analysis
(d)
Interpretation: An efficient synthesis for the given transformations has to be proposed.
Concept Introduction:
Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids. This reaction is catalyzed by Lewis acids like anhydrous AlCl3, FeX3, ZnCl2, BF3 etc.
Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.
A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.
To find: Propose an efficient synthesis for the given transformation (d)
Apply a retrosynthetic analysis
(e)
Interpretation: An efficient synthesis for the given transformations has to be proposed.
Concept Introduction:
Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring. Here are three general steps to an electrophilic aromatic substitution.
- 1) Generation of an electrophile
- 2) Attack of the electrophile on the aromatic ring, creating a resonance-stabilized carbocation called an arenium ion. It loses aromaticity in this step, so the energy of activation is high. Furthermore, this is the rate-determining step of the reaction because of the disruption of aromaticity. The arenium ion is a hybrid resonance structure. There are three general resonance contributors of an arenium ion.
- 3) Deprotonation of the arenium ion by a weak base to regain aromaticity.
Schiemann reaction: It is the reaction in which diazonium salt is converted into fluoro group using fluoroboric acid (HBF4).
A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.
To find: Propose an efficient synthesis for the given transformation (e)
Apply a retrosynthetic analysis
(f)
Interpretation: An efficient synthesis for the given transformations has to be proposed.
Concept Introduction:
Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents. Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.
A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.
To find: Propose an efficient synthesis for the given transformation (f)
Perform elimination-addition process

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Chapter 22 Solutions
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
- Predict the product of this organic reaction: IZ + HO i P+H₂O Specifically, in the drawing area below draw the skeletal ("line") structure of P. If there is no reasonable possibility for P, check the No answer box under the drawing area. No Answer Click and drag to start drawing a structure. ☐ :arrow_forwardPredict the products of this organic reaction: 0 O ----- A + KOH ? CH3-CH2-C-O-CH2-C-CH3 Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click anywhere to draw the first atom of your structure. X ⑤ èarrow_forwardPredict the products of this organic reaction: O CH3 + H2O + HCI A A? CH3-CH2-C-N-CH3 Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. If there's more than one product, draw them in any arrangement you like, so long as they aren't touching. If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click anywhere to draw the first atom of your structure.arrow_forward
- What is the missing reactant in this organic reaction? R+ HO-C-CH2-CH3 0= CH3 CH3 —CH, C−NH—CH CH3 + H₂O Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. Note for advanced students: you may assume no products other than those shown above are formed. No Answer Click anywhere to draw the first atom of your structure. €arrow_forward个 CHEM&131 9267 - $25 - Intro to Mail - Hutchison, Allison (Student x Aktiv Learnin https://app.aktiv.com Draw the product of the reaction shown below. Ignore inorganic byproducts. + Na2Cr2O7 Acetone, H2SO4 Type here to search Dryng OH W Prarrow_forwardPredict the products of this organic reaction: OH + NaOH A? Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click and drag to start drawing a structure. ✓ Sarrow_forward
- Predict the products of this organic reaction: CH3-C-O-CH2-CH2-C-CH3 + H₂O ? A Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click anywhere to draw the first atom of your structure. :☐ darrow_forwardDE d. Draw an arrow pushing mechanism for the following IN O CI N fo 人 P Polle DELL prt sc home end ins F5 F6 F7 F8 F9 F10 F11 F12arrow_forwardPredict the products of this organic reaction: + H₂O H* ? A Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click and drag to start drawing a structure.arrow_forward
- Predict the major organic products of the reaction below and draw them on right side of the arrow. If there will be no significant reaction, check the box below the drawing area instead. C Cl CH, OH There will be no significant reaction. + pyridine G Click and drag to start drawing a structure.arrow_forwardWhat is the missing reactant in this organic reaction? H R+ H2O Δ OH 0= CH3-CH-O-CH3 + CH3-C-OH Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. No Answer Click anywhere to draw the first atom of your structure. dyarrow_forwardYou are trying to determine whether the following organic reaction can be done in a single synthesis step. If so, add any missing reagents or conditions in the drawing area below. If it isn't possible to do this reaction in a single synthesis step, check the box below the drawing area instead. Note for advanced students: if you have a choice of reagents to add, you should choose the least reactive and most economical reagents possible. Cl It isn't possible to do this reaction in a single synthesis step. + T OHarrow_forward
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