Chương 15: Hợp chất cơ kim

Nội dung 1: Cấu trúc, danh pháp, đồng phân

Nội dung 2: Phản ứng

Bài 1. Draw the structures of compounds a–e in the following reaction scheme:

Bài 2. Draw the structures of compounds a–e in the following reaction scheme:

Bài 3. Draw the structures of compounds a–c in the following reaction scheme:
Bài 4. Draw the structure of the product that is expected when the following lactone (cyclic
ester) is treated with two equivalents of MeMgBr followed by aqueous workup:

Bài 5. Draw the product that is expected when each of the following alkenes is treated with
CH2I2 and Zn–Cu:

Bài 6. Draw the coupling product that is expected when the following aryl iodide is treated with
the following organostannane in the presence of Pd(PPh3)4:
Bài 7. For each of the following cases, draw the coupling product that is expected when the
organic electrophile is treated with the organostannane in the presence of catalytic Pd(PPh3)4:

Bài 8. Bombykol is a sex pheromone used by silkworms (females release it to attract the males),
and it can be prepared in the laboratory via a Suzuki coupling reaction between the two partners
shown below:
Bài 9. For each of the following cases, draw the coupling product that is expected when the
organic electrophile is treated with the organoboron compound in the presence of a base and
catalytic Pd(PPh3)4:

Bài 10. Coenzyme Q10 (also called ubiquinone) is a natural product that is found throughout the
human body. It resides in the nonpolar regions of biological membranes and is involved in a
number of essential biochemical processes, including energy generation. It can be prepared using
a Negishi cross-coupling reaction between the following two partners:

Bài 11. For each of the following cases, draw the coupling product that is expected when the
organic electrophile is treated with the organozinc in the presence of catalytic Pd(PPh3)4:
Bài 12. Draw the products that are expected when each of the following compounds is treated
with a Grubbs catalyst:

Bài 13. Draw the product that is expected when each of the following compounds is treated with
a Grubbs catalyst:
Bài 14. Draw the expected product for each of the following coupling reactions:

Bài 15. Draw the expected product for each of the following coupling reactions:
 Chương 16 – Alcol
Nội dung 1: Danh pháp, đồng phân

Bài 1. Assign an IUPAC name for the following alcohol:

Bài 2. Provide an IUPAC name for each of the following alcohols:

Bài 3. Assign an IUPAC name for each of the following compounds:

Bài 4. Draw the structure of each compound:

(a) cis-1,2-Cyclohexanediol (b) Isobutanol
(c) 2,4,6-Trinitrophenol (d) (R)-2,2-Dimethyl-3-heptanol
(e) Ethylene glycol (f) (S)-2-Methyl-1-butanol

Bài 5. Draw and name all constitutionally isomeric alcohols with the molecular formula C4H10O

Bài 6. Give IUPAC substitutive names for the following alcohols:

Bài 7. Give bond-line formulas and appropriate names for all of the alcohols and ethers with the
formulas
(a) C3H8O (b) C4H10O.

Bài 8. Give an IUPAC substitutive name for each of the following alcohols:

Bài 9. Write structural formulas for each of the following:

(a) (Z)-But-2-en-1-ol (d) 1-Ethylcyclobutanol (g) 2-Ethoxypentane
(b) (R)-Butane-1,2,4-triol (e) 2-Chlorohex-3-yn-1-ol (h) Ethyl phenyl ether
(c) (1R,2R)-Cyclopentane-1,2-diol (f) Tetrahydrofuran (i) Diisopropyl ether
(j) 2-Ethoxyethanol

Bài 10.Give IUPAC names for the following compounds:

Bài 11.Draw structures corresponding to the following IUPAC names:

(a) (Z)-2-Ethyl-2-buten-1-ol (b) 3-Cyclohexen-1-ol
(c) trans-3-Chlorocycloheptanol (d) 1,4-Pentanediol
(e) 2,6-Dimethylphenol (f ) o-(2-Hydroxyethyl)phenol
Nội dung 2: Cho chất nền A, hỏi sản phẩm là gì nếu cho phản ứng với các tác chất khác
nhau

Bài 1. Predict the product for the following reaction:

Bài 2. Predict the major product for each reaction:

Bài 3. Predict the products for each of the following transformations:

Bài 4. Predict the major organic product of the following reaction:

Bài 5. Predict the major organic product for each of the following reactions:
Bài 6. Predict the major product of the reaction between 1-butanol and:
(a) PBr3 (b) SOCl2, py
(c) HCl, ZnCl2 (d) DMP, CH2Cl2
(e) Na2Cr2O7, H2SO4, H2O (f) Li
(g) NaH (h) TMSCl, Et3N
(i) TsCl, pyridine (j) Na
(k) Potassium tert-butoxide

Bài 7. Predict the product and draw a mechanism for each of the following reactions:
Bài 8. Predict the products for each of the following

Bài 9. Considering A–L to represent the major products formed in each of the following
reactions, provide a structure for each of A through L. If more than one product can reasonably
be conceived from a given reaction, include those as well.
Bài 10. Predict the major product from each of the following reactions.
 Chương 17: Phenol

Nội dung 2: Phản ứng

Bài 1. Predict the products of each of the following reactions.

Bài 2. What are compounds A and B in the following sequence?

Bài 3. Complete the following equations:

Bài 4. Predict the product of the following reactions.

 Chương 18: Ether

Nội dung 1: Cấu trúc, danh pháp, đồng phân

Bài 1. Name the following compounds:

Bài 2. Provide an IUPAC name for each of the following compounds:

Bài 3. Draw a structure for each of the following compounds:

(a) (R)-2-Ethoxy-1,1-dimethylcyclobutane
(b) Cyclopropyl isopropyl ether

Bài 4. Assign an IUPAC name for each of the following compounds:

Bài 5. Draw all constitutionally isomeric ethers with the molecular formula C4H10O. Provide a
common name and a systematic name for each isomer.

Bài 6. Name the following ethers:

Bài 7. Give a common name (when possible) and a systematic name for each compound. Give a
common name (when possible) and a systematic name for each compound.
Bài 8. Name the following heterocyclic ethers

Bài 9. Write structural formulas for the following compounds

(a) ethyl isopropyl ether (b) di-n-butyl ether (c) 2-ethoxyoctane
(d) divinyl ether (e) allyl methyl ether (f) cyclohexene oxide
(g) cis-2,3-epoxyhexane (h) (2R,3S)-2-methoxypentan-3-ol (i) trans-2,3-dimethyloxirane

Bài 10. Give IUPAC names for the following compounds.

Nội dung 2: Phản ứng

Bài 1. Predict the products for each of the following:

Bài 2. Predict the product for each of the following reaction sequences:

Bài 3. Fill in the missing products below.

Bài 4. Predict the products from each of the following reactions.

Bài 5. Predict the products of the following reaction:

Bài 6. What product would you expect from Claisen rearrangement of 2-butenyl phenyl ether?

Bài 7. Predict the major product of the following reaction:

Bài 8. Predict the major product of each of the following reactions:

Bài 9. Predict the major product of the following reactions:

Bài 10. Predict the products of the following ether cleavage reactions:

Nội dung 3: Tính chất vật lý

Bài 1. Arrange these compounds in order of increasing solubility in water.

Bài 2. Arrange these compounds in order of increasing boiling point.

 I

II III

Bài 3. Each compound given in this problem is a common organic solvent. From each pair of
compounds, select the solvent with the greater solubility in water.

Bài 4. Rank the following compounds in order of increasing boiling point.

I II III

Bài 5. Glycerol (propane-1,2,3-triol) is a viscous syrup with molecular weight 92 g>mol,

boiling point 290 °C, and density 1.24 g>mL. Transforming the three hydroxy groups into their
trimethylsilyl ethers (using chlorotrimethylsilane and a tertiary amine) produces a liquid that
flows easily, has molecular weight 309 g>mol, boiling point approximately 180 °C, and density
0.88 g>mL. Draw the structures of these two compounds, and explain why glycerol has a lower
molecular weight but a much higher boiling point and density.

Bài 6. 1,2-Propanediol (propylene glycol) and 1,3-propanediol (trimethylene glycol) have

higher boiling points than any of the butyl alcohols (see Table 11.1), even though they all have
roughly the same molecular weight. Propose an explanation.
 Chương 19: Aldehyde – Cetone, Quinone

Nội dung 1: Cấu trúc, danh pháp, đồng phân

Bài 1. Provide a systematic (IUPAC) name for the following compound:

Bài 2. Assign a systematic (IUPAC) name to each of the following compounds:

Bài 3. Draw the structure of each of the following compounds:

(a) (S)-3,3-Dibromo-4-ethylcyclohexanone (b) 2,4-Dimethyl-3-pentanone
(c) (R)-3-Bromobutanal

Bài 4. Name the following compounds:

Bài 5. Provide a structure for each:

(a) (2-Hydroxy-4-methoxyphenyl)-phenylmethanone (also known as oxybenzone).
(b) 1-(4-Methoxyphenyl)-3-[4-(1,1-dimethylethyl)phenyl]propane-1,3-dione (also known as
avobenzone).
Bài 6. Provide a systematic (IUPAC) name for each of the following compounds:

Bài 7. Draw the structure for each compound below:

(a) Propanedial
(c) (S)-3-Phenylbutanal
(e) (R)-3-Hydroxypentanal
(g)2,4,6-Trinitrobenzaldehyde
(i) (3R,4R)-3,4-Dihydroxy-2-pentanone
(b) 4-Phenylbutanal
(d) 3,3,5,5-Tetramethyl-4-heptanone
(f) meta-Hydroxyacetophenone
(h) Tribromoacetaldehyde

Bài 8. Provide a systematic (IUPAC) name for the compound below. Be careful: This
compound has two chiral centers (can you find them?)

Bài 9. Draw all constitutionally isomeric aldehydes with the molecular formula C4H8O and
provide a systematic (IUPAC) name for each isomer.

Bài 10. Draw all constitutionally isomeric aldehydes with the molecular formula C5H10O and
provide a systematic (IUPAC) name for each isomer. Which of these isomers possesses a chiral
center?

Bài 11. Draw all constitutionally isomeric ketones with the molecular formula C 6H12O and
provide a systematic (IUPAC) name for each isomer.
Nội dung 2: Phản ứng của aldehyde -cetone

Bài 1. Predict the product(s) for each reaction below:

Bài 2. Predict the major product for each of the following reactions:

Bài 3. Predict the product of each of the following reactions:

Đáp án

a) b)

Bài 4. Predict the major product for each of the following reactions:
Bài 5. Predict the product of the following two-step procedure:

Bài 6. Draw the products that are expected from the following reaction:

Bài 7. Draw the products that are expected for each of the following reactions:
Bài 8. Predict the major product for each of the following:

Bài 9. Predict the major product(s) for each of the following reactions:
Bài 10. Predict the major product(s) for each of the following:

Bài 11. Predict the major product for each of the following reaction sequences:

Bài 12. Predict the major product of the following reaction:

Bài 13. Predict the major product of each reaction below:

Bài 14. Predict the major product(s) from the treatment of acetone with the following:
(a) [H+], NH3, (−H2O) (b) [H+], CH3NH2, (−H2O)
(c) [H+], excess EtOH, (−H2O) (d) [H+], (CH3)2NH, (−H2O)
(e) [H ], NH2NH2, (−H2O)
+
(f) [H+], NH2OH, (−H2O)
(g) NaBH4, MeOH (h) RCO3H
(i) HCN, KCN (j) EtMgBr followed by H2O
(k) (C6H5)3P=CHCH2CH3 (l) LiAlH4 followed by H2O

Nội dung 3: Tính chất vật lý

Bài 1. Which compound in each of the following pairs has the higher boiling point?
(a) Pentanal or 1-pentanol (c) Pentane or pentanal (e) Benzaldehyde or benzyl alcohol
(b) 2-Pentanone or 2-pentanol (d) Acetophenone or 2-phenylethanol
 Chương 19: Acid carboxylic

Nội dung 1: Cấu trúc, danh pháp, đồng phân

Bài 1. Provide both an IUPAC name and a common name for each of the following compounds:
(a) HO2C(CH2)3CO2H (b) CH3(CH2)2CO2H
(c) C6H5CO2H (d) HO2C(CH2)2CO2H
(e) CH3COOH (f) HCO2H

Bài 2. Draw the structure of each of the following compounds:

(a) Cyclobutanecarboxylic acid (b) 3,3-Dichlorobutyric acid
(c) 3,3-Dimethylglutaric acid

Bài 3. Provide an IUPAC name for each of the following compounds:

Bài 4. Give an IUPAC systematic name for the following compound.

Bài 5. Give an IUPAC systematic name for each of the following:

Bài 6. Write a structural formula for each of the following compounds:

(a) Octanoic acid
(b) Propanamide
(c) N,N-Diethylhexanamide
(d) 2-Methyl-4-hexenoic acid
(e) Butanedioic acid (j) Benzyl acetate
(f)1,2-Benzenedioic acid (phthalic acid)
(g) 1,4-Benzenedioic acid (terephthalic acid)
(h) Acetic anhydride
(i) Isobutyl propanoate
(k) Ethanoyl chloride (acetyl chloride)
(l) 2-Methylpropanenitrile
(m) Ethyl 3-oxobutanoate (ethyl acetoacetate)
(n) Diethyl propanedioate (diethyl malonate)

Bài 7. Give an IUPAC systematic or common name for each of the following compounds:

Bài 8. Give IUPAC names for the following compounds:

Bài 9. Draw structures corresponding to the following IUPAC names:

(a) 2,3-Dimethylhexanoic acid (b) 4-Methylpentanoic acid
(c) trans-1,2-Cyclobutanedicarboxylic acid (d) o-Hydroxybenzoic acid
(e) (9Z,12Z)-9,12-Octadecadienoic acid (f) 2-Pentenenitrile

Bài 10. Draw and name the eight carboxylic acids with the formula C6H12O2
Nội dung 2: Phản ứng

Bài 1. Predict the major product(s) formed when cyclopentanecarboxylic acid is treated with
each of the following reagents:
(a) SOCl2 (b) LiAlH4 (excess), followed by H2O
(c) NaOH (d) [H+], EtOH

Bài 2. Predict the major product(s) for each of the following reactions:

Bài 3. Predict the product of the reaction of p-methylbenzoic acid with each of the following:
(a) LiAlH4, then H3O+ (b) N-Bromosuccinimide in CCl4
(c) CH3MgBr in ether, then H3O+ (d) KMnO4, H3O+
Bài 4. Write structural formulas for the major organic products from each of the following
reactions
Nội dung 3: Tính chất vật lý

Bài 1. Explain why the boiling point of CH3CONH2 (221 °C) is significantly higher than the
boiling point of CH3CO2H (118 °C).
 Chương 21: Các dẫn xuất của acid carboxylic
Nội dung 1: Cấu trúc danh pháp, đồng phân

Bài 1. Provide a name for each of the following compounds:

Bài 2. Draw a structure for each of the following compounds:

(a) Dimethyl oxalate (b) Phenyl cyclopentanecarboxylate
(c) N-Methylpropionamide (d) Propionyl chloride

Bài 3. Give IUPAC names for the following compounds:

Bài 4. Give IUPAC names for the following substances:

Bài 5. Draw structures corresponding to the following names:
(a) Phenyl benzoate (b) N-Ethyl-N-methylbutanamide
(c) 2,4-Dimethylpentanoyl chloride (d) Methyl 1-methylcyclohexanecarboxylate
(e) Ethyl 3-oxopentanoate (f ) Methyl p-bromobenzenethioate
(g) Formic propanoic anhydride (h) cis-2-Methylcyclopentanecarbonyl bromide

Bài 6. Give IUPAC names for the following compounds:

Bài 7. Draw structures corresponding to the following names:
(a) p-Bromophenylacetamide (b) m-Benzoylbenzamide
(c) 2,2-Dimethylhexanamide (d) Cyclohexyl cyclohexanecarboxylate
(e) Ethyl 2-cyclobutenecarboxylate (f) Succinic anhydride

Bài 8. Draw and name compounds that meet the following descriptions:
(a) Three acid chlorides having the formula C6H9ClO
(b) Three amides having the formula C7H11NO

Bài 9. Draw the structures of eight different carboxylic acids with the molecular formula
C6H12O2. Then, provide a systematic name for each compound and identify which three isomers
exhibit chiral centers.

Bài 10. Draw and name all constitutionally isomeric acid chlorides with the molecular formula
C4H7ClO. Then provide a systematic name for each isomer
Nội dung 2: Phản ứng

Bài 1. Predict the major product(s) for each of the following reactions:

Bài 2. Predict the major product(s) for each of the following reactions:

Bài 3. Predict the major product(s) for each of the following reactions:

Bài 4. Predict the major product(s) for each of the following reactions:
Bài 5. Predict the major product(s) formed when hexanoyl chloride is treated with each of the
following reagents:
(a) CH3CH2NH2 (excess) (b) LiAlH4 (excess), followed by H2O
(c) CH3CH2OH, pyridine (d) H2O, pyridine
(e) C6H5CO2Na (f) NH3 (excess)
(g) Et2CuLi (h) EtMgBr (excess), followed by H2O

Bài 6. What major organic product would you expect to obtain when acetyl chloride reacts with
each of the following?

Bài 7. What major organic product would you expect to obtain when acetic anhydride reacts
with each of the following?
(a) NH3 (excess) (c) CH3CH2CH2OH (e) CH3CH2NH2 (excess)
(b) H2O (d) C6H6 + AlCl3 (f) (CH3CH2)2NH (excess)

Bài 8. What major organic product would you expect to obtain when succinic anhydride reacts
with each of the following
(a) NH3 (excess) (c) CH3CH2CH2OH (e) CH3CH2NH2 (excess)
(b) H2O (d) C6H6 + AlCl3 (f) (CH3CH2)2NH (excess)

Bài 9. What products would you expect to obtain when ethyl propanoate reacts with each of the
following?
(a) H3O+, H2O (c) 1-Octanol, HCl (e) LiAlH4, then H2O
(b) HO-, H2O (d) CH3NH2 (f) Excess C6H5MgBr, then H2O, NH4Cl
Bài 10. Write structural formulas for the major organic products from each of the following
reactions.
Chương 22: Amin

Nội dung 1: Cấu trúc, danh pháp, đồng phân

Bài 1. Assign a name for the following compound:

Bài 2. Assign a name for each of the following compounds:

Bài 3. Draw the structure of each of the following compounds:

(a) Cyclohexylmethylamine (b)Tricyclobutylamine (c)2,4-Diethylaniline
(d) (1R,2S)-2-Methylcyclohexanamine (e) ortho-Aminobenzaldehyde

Bài 4. Draw the structure of each of the following compounds:

(a) N-Ethyl-N-isopropylaniline (b) N,N-Dimethylcyclopropylamine
(c) (2R,3S)-3-(N,N-Dimethylamino)-2-pentanamine (d)Benzylamine

Bài 5. Assign a name for each of the following compounds:

Bài 6. Draw all constitutional isomers with the molecular formula C4H11N and provide a name
for each isomer.

Bài 7. Draw all tertiary amines with the molecular formula C5H13N and provide a name for each
isomer. Are any of these compounds chiral?

Bài 8. Write structural formulas for each of the following compounds:

(a) Benzylmethylamine (k) Dimethylaminium chloride
(b) Triisopropylamine (l) 2-Methylimidazole
(c) N-Ethyl-N-methylaniline (m) 3-Aminopropan-1-ol
(d) m-Toluidine (n) Tetrapropylammonium chloride
(e) 2-Methylpyrrole (o) Pyrrolidine
(f) N-Ethylpiperidine (p) N,N-Dimethyl-p-toluidine
(g) N-Ethylpyridinium bromide (q) 4-Methoxyaniline
(h) 3-Pyridinecarboxylic acid (r) Tetramethylammonium hydroxide
(i) Indole (s) p-Aminobenzoic acid
(j) Acetanilide (t) N-Methylaniline

Bài 9. Give common or systematic names for each of the following compounds:
Nội dung 2: Phản ứng

Bài 1. Draw the major product obtained when 3-methyl-3-hexanamine is treated with excess
methyl iodide followed by aqueous silver oxide and heat.

Bài 2. Draw the major product that is expected when each of the following compounds is treated
with excess methyl iodide followed by aqueous silver oxide and heat:
(a) Cyclohexylamine (b) (R)-3-Methyl-2-butanamine
(c) N,N-Dimethyl-1-phenylpropan-2-amine

Bài 3. Predict the major product obtained when each of the following amines is treated with a
mixture of NaNO2 and HCl:

Bài 4. Draw the structure of the major product obtained when aniline is treated with each of the
following reagents:
(a) Excess Br2 (b) PhCH2COCl, py
(c) Excess methyl iodide (d) NaNO2 and HCl followed by H3PO2
(e) NaNO2 and HCl followed by CuCN

Bài 5. One variation of the Gabriel synthesis employs hydrazine to free the amine in the final
step of the synthesis. Draw the by-product obtained in this process.

Bài 6. Predict the major product for each of the following reactions:
Bài 7. Draw the product formed when each of the following compounds is treated with NaNO2
and HCl:

Bài 8. Draw the major product(s) that are expected when each of the following amines is treated
with excess methyl iodide and then heated in the presence of aqueous silver oxide.

Bài 9. Predict the major product(s) for each of the following reactions:
Bài 10.meta-Bromoaniline was treated with NaNO2 and HCl to yield a diazonium salt. Draw the
product obtained when that diazonium salt is treated with each of the following reagents:

(a) H2O (b) HBF4 (c) CuCN (d) H3PO2 (e) CuBr