CHEM 2312 Midterm: CHEM 2312 GT Examp3ii

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15 Feb 2019

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E3 practice ii: (32 points) circle the letter on the right which corresponds to the answer to each question. L (iv) which of the following best describes the mechanism for the formation of an acetal by the reaction between an aldehyde and an alcohol in the presence of an acid: electrophilic addition followed by an elimination. M. nucleophilic addition followed by an sn1 reaction. Oh: h2/pt, lialh4, nabh4, na2cr2o7 (vii) which of the following reactions does not give benzaldehyde as the major product, treatment of benzyl alcohol with pcc, reaction of benzoyl chloride, phcocl, with nabh4. Cc. reduction of a carboxylic acid with lialh4 dd. Ff. treatment of a grignard reagent with ethylene oxide. Ff: (38 points) (a) provide the structure of the major organic products obtained from the first four reactions, and the synthetic intermediate and product for the last two schemes.

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

(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) COCH_3, 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 Cï¿½C 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) COCH_3, 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 ï¿½ï¿½ 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) H₂SO_4.SO₃ (B) H₂SO_4.SO₂ (C) H₂SO_4.HSO₂ (D) H₂SO_4.HSO₃ (E) H₂SO_4.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

(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

lilacwater-buffalo25

Balance the following Chemical Equations:

____Fe(s) + ____H₂O(g) Â® ____Fe₃O₄(s) + ____H₂(g)

____C₂H₆(g) + ____O₂(g) Â® ____CO₂(g) + ____H₂O(g)

___ C₆H₁₄ (l) + ___ O₂ (g) Â® ___ CO₂ (g) + ___ H₂O (g)

___ C₃H₈O₃ (l) + ___ O₂ (g) Â® ___ CO₂ (g) + ___ H₂O (l)

___ NaN₃ (s) Â® ___ Na (s) + ___ N₂ (g)

__ C₃H₅N₃O₉ Â® __ CO₂ + ___ N₂ + ___ H₂O + ___ O₂

Write and Balance the equations:

Aqueous calcium hydroxide reacts with aqueous sodium carbonate to produce solid calcium carbonate and aqueous sodium hydroxide.

Solid iron reacts with Oxygen gas to form solid Iron (II) oxide

Copper(II) sulfide is oxidized by molecular oxygen to produce gaseous sulfur trioxide and solid copper(II) oxide. The gaseous product then reacts with liquid water to produce liquid hydrogen sulfate as the only product. Write the two equations which represent these reactions.

Indicate what type, or types, of reaction each of the following represents: (precipitation, acid-base, and oxidation-reduction.)

(A) H₂O(g) + C(s) â¶ CO(g) +H₂(g)

(B) 2KClO₃(s) â¶ 2KCl(s) +3O₂(g)

(D) Pb(NO₃)₂(aq) + H₂SO₄(aq) â¶ PbSO₄(s) + 2HNO₃(aq)

4. Silver can be separated from gold because silver dissolves in nitric acid while gold does not. Is the dissolution of silver in nitric acid an acid-base reaction or an oxidation-reduction reaction? Explain your answer.

5. Determine the oxidation states of the elements in the compounds listed. None of the oxygen-containing compounds are peroxides or superoxides.

(A) H₃PO₄

(B) Al(OH)₃

6. Complete and balance the following acid-base equations:

(A) A solution of HClO₄ is added to a solution of LiOH.

(B) Aqueous H₂SO₄ reacts with NaOH.

7. Write the molecular, total ionic, and net ionic equations for the following reactions:

(A) Ca(OH)₂(aq) + HC₂H₃O₂(aq) â¶

(B) H₃PO₄(aq) + CaCl₂(aq) â¶

8. Write the balanced equation, then calculate the number of moles and the mass of Mg required to react with 5.00 g of HCl and produce MgCl₂ and H₂. Ans: 1.67 g Mg

9. H₂ is produced by the reaction of 118.5 mL of a 0.8775-M solution of H₃PO₄ according to the following equation: 2Cr + 2H₃PO₄ â¶ 3H₂ + 2CrPO₄. How many grams of H₂ are produced? Ans: .315 g H₂

10. Automotive air bags inflate when a sample of sodium azide, NaN₃, is very rapidly decomposed.

2NaN₃(s) â¶ 2Na(s) + 3N₂(g)

What mass of sodium azide is required to produce 2.6 ft³ (73.6 L) of nitrogen gas with a density of 1.25 g/L?

Ans: 142 g NaN₃

11. Urea, CO(NH₂)₂, is manufactured on a large scale for use in producing urea-formaldehyde plastics and as a fertilizer. What is the maximum mass of urea that can be manufactured from the CO₂ produced by combustion of 1.00 x 10⁴ grams of CO₂?

CO₂(g) + 2NH₃(g) â¶ CO(NH₂)₂(s) + H₂O(l)

Ans: 1360 g urea

12. What volume o f 0.750 M hydrochloric acid solution can be prepared from the HCl produced by the reaction of 25.0 g of NaCl with excess sulfuric acid? NaCl(s) + H₂SO₄(l) â¶ HCl(g) + NaHSO₄(s)

Ans: .570 L

13. A sample of 0.53 g of carbon dioxide was obtained by heating 1.31 g of calcium carbonate. What is the percent yield for this reaction? CaCO₃(s)â¶CaO(s) + CO₂(s)

Ans: 92.0 %

14. Citric acid, C₆H₈O₇, a component of jams, jellies, and fruity soft drinks, is prepared industrially via fermentation of sucrose by the mold Aspergillus niger. The equation representing this reaction is

C₁₂H₂₂O₁₁ + H₂O +3O₂ â¶2C₆H₈O ₇+ 4H₂O

What mass of citric acid is produced from the reaction of 150. grams of sucrose if the yield is 92.30%?

Ans: 155 g

15. The phosphorus pentoxide used to produce phosphoric acid for cola soft drinks is prepared by burning phosphorus in oxygen.

(A) What is the limiting reactant when 0.200 mol of P₄ and 0.200 mol of O₂ react according to P₄+5O₂ â¶ P₄O₁₀?

(B) Calculate the percent yield if 10.0 g of P₄O₁₀ is isolated from the reaction.

Ans: 88.0 %

16. What is the limiting reactant when 1.50 g of lithium and 1.50 g of nitrogen combine to form lithium nitride, a component of advanced batteries, according to the following unbalanced equation? Li + N₂ â¶ Li₃N

Ans: Li

17. What is the concentration of NaCl in a solution if titration of 15.00 mL of the solution with 0.2503 M AgNO₃ requires 20.22 mL of the AgNO₃ solution to reach the end point?

AgNO₃(aq) + NaCl(aq) â¶ AgCl(s) +NaNO (aq)

Ans: .3374 M

18. In a common medical laboratory determination of the concentration of free chloride ion in blood serum, a serum sample is titrated with a Hg(NO₃)₂ solution.

2Cl^â(aq) + Hg(NO₃)₂(aq) â¶ 2NO₃^â(aq) + HgCl₂(s)

What is the Cl^â concentration in a 0.25-mL sample of normal serum that requires 1.46 mL of .000825 M Hg(NO₃)₂(aq) to reach the end point?

Ans: 0.009636 M

CHEM 2312 Midterm: CHEM 2312 GT Examp3ii

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