Concept explainers
(a)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Organolithium compounds can be formed by the reaction of
Answer:
The synthesis of given compound from given starting material is shown below.
Explanation:
The given compound
Figure 1
Conclusion:
The synthesis of given compound is shown in Figure 1.
Answer to Problem 21.56AP
The synthesis of given compound from given starting material is shown below.
Explanation of Solution
The given compound
Figure 1
The synthesis of given compound is shown in Figure 1.
(b)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Grignard reagent is formed when alkyl halide compound reacts with magnesium in presence of ether. Potassium dichromate is a strong oxidizing agent. It can easily oxidize alcohol group to
Answer to Problem 21.56AP
The synthesis of given compound from given starting material is shown below.
Explanation of Solution
Bromocyclohexane when reacted with magnesium in the ether, it will form grignard reagent. Then grignard reagent will react with
Figure 2
The synthesis of given compound is shown in Figure 2.
(c)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
The carboxylic acid compound reacts with ammonia to form the amide compound. The carbonyl carbon of acid is electrophilic in nature and the lone pair of nitrogen atom of ammonia acts as nucleophile. They will undergo the nucleophilic substitution reaction. Lithium aluminium hydride is a strong reducing agent.
Answer to Problem 21.56AP
The synthesis of given compound from given starting material is shown below.
Explanation of Solution
The phthalic acid reacts with ammonia, the lone pair of ammonia nitrogen attacks the carbonyl carbon atom and then with the removal of water molecule phthalamic acid is formed. Then phthalamic acid undergoes cyclization reaction to form phthalamide. Phthalamide upon reduction with lithium aluminium hydride e form the desired product. The synthesis of the given compound is shown below.
Figure 3
The synthesis of given compound is shown in Figure 3.
(d)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Acid can be converted into acid chloride by the reaction of acid with
Answer to Problem 21.56AP
The synthesis of given compound from given starting material is shown below.
Explanation of Solution
The isovaleric acid reacts with
Figure 4
The synthesis of given compound is shown in Figure 4.
(e)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Sodium borohyride is a reducing agent. It reduces the
Answer to Problem 21.56AP
The synthesis of given compound from given starting material is shown below.
Explanation of Solution
The given starting material reacts with sodium borohydride to convert the carbonyl group into the alcohol group. The reaction of alcohol with hydrogen bromide forms bromoalkene compound. Bromoalkene reacts with the sodium cyanide to form nitrile compound. The nitrile upon reduction forms amine. The amine functional group when reacts with the acid chloride it forms the amide. The synthesis is shown below.
Figure 5
The synthesis of given compound is shown in Figure 5.
(f)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Cyanohydrin can be formed on reaction of ketone with cyanide. It is a nucleophilic addition reaction. The cyanide ion acts as nucleophile and carbonyl carbon is electrophile. Nitrile group can be converted into amine by reduction with lithium aluminium hydride.
Answer to Problem 21.56AP
The synthesis of given compound from given starting material is shown below.
Explanation of Solution
Ketones react with the hydrogen cyanide to form cyanohydrin. The cyanide ion acts as the nucleophile and attacks the electrophilic carbon of the carbonyl group. The cyano hydrin formed will undergo reduction in presence of lithium aluminium hydride to reduce the cyanide group to amine group. The synthesis of the given compound is shown below.
Figure 6
The synthesis of given compound is shown in Figure 6.
(g)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Nitration reaction is the reaction in which nitro derivatives are formed. The mixture of nitric acid and sulfuric acid is used as the nitrating mixture. Benzoic acid upon nitration form meta nitrobenzoic acid. The reaction of carboxylic acid with sodium hydroxide produces sodium salt of carboxylic acid.
Answer to Problem 21.56AP
The synthesis of given compound is shown below.
Explanation of Solution
The benzoic acid undergoes nitration reaction in presence of nitric acid and sulfuric acid. The meta product is formed upon nitration of benzoic acid. The meta-nitrobenzoic acid is formed on nitration of benzoic acid. Sodium salt of benzoic acid is formed when benzoic acid reacts with sodium hydroxide. The reaction between the meta-nitrobenzoic acid and sodium salt of benzoic acid forms the desired product. The synthesis of the given compound is shown below.
Figure 7
The synthesis of given compound is shown in Figure 7.
(h)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Acid can be converted into acid chloride by the reaction of acid with
Answer to Problem 21.56AP
The synthesis of given compound is shown below.
Explanation of Solution
The carboxylic acid group is converted into the acid chloride group by reaction of acid with thionyl chloride. Acid chloride undergoes catalytic reduction to form aldehyde group. Methyl magnesiumbromide converted the product into alkylated secondary alcohol. The formed hydroxy ester compound undergoes cyclization reaction to form the lactone. The synthesis of the given compound is shown below.
Figure 8
The synthesis of given compound is shown in Figure 8.
(i)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Potassium permanganate is a strong oxidizing agent. It will oxidize the alkyl group directly to the carboxylic acid group. Thionyl chloride is used for chlorinating the carboxylic acid group. Acid chloride and amines reacts to form the amide linkage.
Answer to Problem 21.56AP
The synthesis of given compound is shown below.
Explanation of Solution
The compound,
Figure 9
The synthesis of given compound is shown in Figure 9.
(j)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Chloro formic esters and carbonates are formed when phosgene reacts with alcohol compounds. The carbon of phosgene is electrophilic in nature. The phosgene reacts with alcohol and amines. Lone pair of oxygen atom in the alcohol compounds acts as the nucleophilie. Thus nucleophilic substitution reaction can occur.
Answer to Problem 21.56AP
The synthesis of given compound is shown below.
Explanation of Solution
Phosgene has an electrophilic carbon centre. The lone pair of oxygen atom of alcohol acts as nucleophile and attacks at the electrophilic carbon of phosgene. Chloride ion acts as the leaving group. The phosgene reacts with methanol to form methyl chloroformate. Then methyl chloroformate reacts with phenol to form the methyl phenyl carbonate. The complete synthesis is shown below.
Figure 10
The synthesis of given organic compound is shown in Figure 10.
(k)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
The formation of biaryls by the coupling of aryl halides is known as Ullmann reaction. The reaction takes place in the presence of copper. The reaction proceeds via radical mechanism. The thoinyl chloride reacts with acid to form acid chloride. Potassium permangenate is a strong oxidizing agent which convert alkyl group directly into acid group.
Answer to Problem 21.56AP
The synthesis of given organic compound is shown below.
Explanation of Solution
The
Figure 11
The synthesis of given compound is shown in Figure 11.
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Chapter 21 Solutions
Organic Chemistry
- Introduce the reaction and structure of the expected products (indicate the main product, when possible) for a reaction of 3-ethyl-5-methyl-hex-2-ene with the following reagents: (a) Br2, CH2Cl2 (b) H2O , Diluted H2SO4.arrow_forwardDo the reactions and he explains why.arrow_forward(b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3arrow_forward
- (c)Show step by step how to synthesize methoxybenzene from benzene.arrow_forward(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward(a) A hydrocarbon isolated from fish oil and from plankton was identified as 2,6,10,14-tetramethyl-2-pentadecene. Write its structure.(b) Alkyl isothiocyanates are compounds of the type RN C S. Write a structural formula for allyl isothiocyanate, a pungent-smelling compound isolated from mustard.(c) Grandisol is one component of the sex attractant of the boll weevil. Write a structural formula for grandisol given that R in the structure shown is an isopropenyl group.arrow_forward
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.arrow_forward(a) Account for the following :(i) Cl – CH2COOH is a stronger acid than CH3COOH.(ii) Carboxylic acids do not give reactions of carbonyl group.(b) Write the chemical equations to illustrate the following name reactions:(i) Rosenmund reduction (ii) Cannizzaro’s reaction(c) Out of CH3CH2 – CO – CH2 – CH3 and CH3CH2 – CH2 – CO – CH3, which gives iodoform test?arrow_forwardThe endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rainforests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.arrow_forward
- Predict the products of the following reactions.(a) sec-butyl isopropyl ether + concd. HBr, heatarrow_forwardDeduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC¬(CH2)6¬COOH. Draw the structure of W.(b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethylsulfide, gives two equivalents of butanedial, O“CH¬CH2CH2¬CH“O. Draw the structure of X.(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethylsulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.*(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reductionwith dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (¬CH2¬CH2¬CHO) group on C1 and aone-carbon aldehyde (¬CHO) group on C2. Draw the…arrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward