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12 Nov 2019

a) List the steps needed (i.e. list the reagents, show the mechanism) needed to carry out the following synthesis



List of reagents:

Friedel-Crafts alkylation
Friedel-Crafts acylation
Birch reduction
Wolff-Kishner reduction
Cr(VI) oxidation
Lewis acid catalyzed bromination
nitration
sulfonation


b) Using the same reagent list above, put in order the reagent steps needed to convert benzene to p-nitrobenzoic acid in the least amount of steps as possible

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Trinidad Tremblay
Trinidad TremblayLv2
5 Sep 2019

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Related questions

1. Which of the following reagent(s) can be used to prepare a mixture of o and p-nitro toluene from toluene

(A) HNO2 (B) HNO3 (C) HNO3/Fe (D) HNO3/H2SO4 (E) NaNO2

2.

(A) H2SO3 (B) SO3/ Which of the following reagent(s) can be used to convert nitrobenzene to m-nitrobenzenesulfonic acid Fe (C) H2SO3/Fe (D) H2SO4/Al2(SO4)3 (E) H2SO4.SO3

3. Which of the following reagent(s) can be used to prepare bromobenzene from benzene

(A) NBS (B) Br2/FeBr3 (C) H2SO4/Br2 (D) Br2/AlBr3 (E) Br2/Pd

4. Which of the following functional groups are o,p-directing ?

(A) Br, CH2CH3, NH2 (B) Cl, NH2, COOH (C) I, SO3H, OH (D) OCH3, Cl, COCH3 (E) NO2, CH3, OH

5. Which of the following reagent(s) gives the reaction below

(A) CH3Cl (B) Cl2/ Fe (C) Cl2/ AlCl3 (D) Cl2/ FeCl3 (E) Cl2/ HCl

6. Friedal-Craft acylation reagent(s)

(A) CH3Cl/AlCl3 (B) Cl2/CH3COCl (C) CH3COCl/AlCl3 (D) CH3COCl/FeCl3 (E) CH3Cl/FeCl3

7. Which of the following functional groups are m-directing ?

(A) NO2, CH3, OH (B) Br, NH2, COOH (C) I, SO3H, OH (D) OCH3, Cl, COCH3 (E) COCH3, SO3H, CHO

8. Which of the following compound can be used in the Diels-Alder reaction

(A) 2-methyl, 2,4-hexadiene (B) 2,5-hexadiene (C) 1-methyl,cyclohexa-1,4-diene (D) cyclohexa-1,4-diene

(E) 2-methyl, 1,5-hexadiene

9. Which statement about benzene is incorrect?

(A) The C�C p - bonding is delocalized (B) The C6 ring is planar (C) The average C - C bond distance is the same as C-C double bonds (D) Each C atom is sp2 hybridized ( E ) There are 12 s (sigma) bonds in benzene

10. Which of the following is NOT aromatic

(A) Cyclopropenyl cation (C3H3+) (B) Benzene (C6H6) (C) [16]-Annulene (C16H16)

(D) Cycloheptatrienyl cation (C7H7+) (E) [18]-Annulene (C18H18)

11. Conjugate addition of one equivalent of deuterium bromide (DBr) to 1,3-butadiene gives

(A) 3-bromo, 4-deutero, 1-butene (B) 3-bromo, 4-deutero, 2-butene (C) 4-bromo, 3-deutero, 1-butene (D) 1-bromo, 4-deutero, 2-butene (E) 1-bromo, 4-deutero, 1-butene

12. Which of the following is a conjugated diene

(A) cyclopentadiene (B) 2-methylcyclohexanone (C) 1-methyl,cyclohexa-1,4-diene (D) cyclohexa-1,4-diene

(E) cycloocta-1,5-diene

13. The aromatic compound is

14. Which of the following reaction involves a benzyne mechanism ?

(A) Ph-CH3 ? Ph-COOH (B) Ph-CH3 ? Ph-CHO (C) Ph-OH ? Ph-Cl (D) Ph-Cl ? Ph-OH

(E) none of these

15. Which of the following reagent(s) can be used to prepare a mixture of o and p-nitro toluene from

toluene

(A) HNO2 (B) HNO3 (C) HNO3/Fe (D) HNO3/H2SO4 (E) NaNO2

16. Friedal-Craft alkyation reagent(s)

(A) C2H5Cl/AlCl3 (B) Cl2/CH3COCl (C) CH3COCl/AlCl3 (D) CH3COCl/FeCl3 (E) CH3Cl/FeCl3

17. Which of the following functional groups are o,p-directing ?

(A) NO2, SO3H, CHO (B) Br, NH2, COOH (C) I, OH, CH3 (D) OCH3, Cl, COCH3 (E) COCH3, SO3H, Br

18. Major product in the reaction of benzene with 1-bromopropane, in the presence of AlBr3 catalyst

(A) bromobenzene (B) n-propylbenzene (C) iso-propylbenzene (D) o-bromo-n-propylbenzene

(E) p-bromo-n-propylbenzene

19. Which of the following is the electrophile in the nitration reaction

(A) +HNO2 (B) NO2+ (C) N2+ (D) HNO3/H2SO4 (E) NO3+

20. Which of the following is the electrophile in the sulfonation reaction

(A) +HSO2 (B) SO2+ (C) SO3+ (D) SO3/H2SO4 (E) HSO3+

21. Which of the following is the electrophile in the Friedel-Craft acylation reaction

(A) RCO2+ (B) RCO+ (C) CO2+ (D) RX/H2SO4 (E) RCO3+

22. The benzyne intermediate has �� p bonds

(A) 1 (B) 2 (C) 3 (D) 4 (E) 5

23. The reagent used for Allylic/benzylic bromination is:

(A) NBS (B) Br2/ Fe (C) Br2/ AlBr3 (D) Br2/ FeBr3 (E) Br2/ HBr

24. Which of the following is an oxidation reagent

(A) H2SO4 (B) KMnO4 (C) KMnO2 (D) NaBH4 (E) AlCl3

25. The formula of fuming sulfuric acid

(A) H2SO4.SO3 (B) H2SO4.SO2 (C) H2SO4.HSO2 (D) H2SO4.HSO3 (E) H2SO4.SO

��������������������������������������������

26. How do you prepare the following compounds, starting from benzene ?

(a). aniline (b). Iodo benzene (c). benzoic acid (d). benzylbromide (e). m-methyl benzoic acid

(f). p-nitrobenzoic acid (g) m-nitrobenzoic acid (h). p-chlorobenzenesulfonic acid (i). m-chlorobenzenesulfonic

acid (j) 3-isopropyl benzoic acid (k). 4-isopropyl toluene

27. Draw the product(s) from the following reactions showing the mechanisms

(a) 1,3-butadiene with acrylonitrile

(b) 1,3-butadiene with one eqv. HBr

(c) 1,3-cyclohexadiene with acrylonitrile

(d) 1,3-cyclohexadiene with one eqv. HBr

(e) 1,3-cyclohexadiene with two eqv. HBr

(f) cyclopentadiene with two eqv. HBr

28. How do you prepare the following compounds, starting from toluene ?

(a). benzoic acid (b). benzyl alcohol (c). m-bromobenzoic acid (d). m-methylbenzoic acid (e). m-nitro

benzoic acid (f). p-nitrobenzoic acid

29. What is/are the product(s) expected when ethylbenzene is reacted with

(a). NBS

(b). Br2/FeBr3

(c). KMnO4, then H+

(d). fuming H2SO4

(e). NBS, then aq. NaOH

(f) iso-butylbromide/AlBr3

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