Chương 13: Alkyn – Hydrocarbon acetylenic

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

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

Đáp án : 4-Ethyl-5-methyl-3-propyl-1-heptyne

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

Đáp án
a) b) c)

d) e)

f) g)

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

(a)4,4-Dimethyl-2-pentyne (b) 5-Ethyl-2,5-dimethyl-3-heptyne

Đáp án

a) b)
Bài 4. Name the following compounds:

Đáp án
Bài 5. There are seven isomeric alkynes with the formula C6H10. Draw and name them.

Bài 6. Give IUPAC names for the following compounds:

Đáp án
Bài 7. Draw structures corresponding to the following names:
(a) 3,3-Dimethyl-4-octyne (b) 3-Ethyl-5-methyl-1,6,8-decatriyne
(c) 2,2,5,5-Tetramethyl-3-hexyne (d) 3,4-Dimethylcyclodecyne
(e) 3,5-Heptadien-1-yne (f) 3-Chloro-4,4-dimethyl-1-nonen-6-yne
(g) 3-sec-Butyl-1-heptyne (h) 5-tert-Butyl-2-methyl-3-octyne

Đáp án

Bài 8. Draw structural formulas of at least two alkynes of each molecular formula.
(1) C6H10 (2) C8H12 (3) C7H8

Bài 9. For each molecular formula, draw all the isomeric alkynes, and give their IUPAC names.
Circle the acetylenic hydrogen of each terminal alkyne.
(a) C5H8 (three isomers) (b) C6H10 (seven isomers)

Bài 10. Write structural formulas for the following compounds (includes both old- and new-style
names).
(a) 2-octyne (b) ethylisopentylacetylene
(c) ethynylbenzene (d) cyclohexylacetylene
(e) 5-methyl-3-octyne (f) trans-3,5-dibromocyclodecyne
(g) 5,5-dibromo-4-phenylcyclooct-1-yne (h) (E)-6-ethyloct-2-en-4-yne
(i) 1,4-heptadiyne (j) vinylacetylene
(k) (S)-3-methyl-1-penten-4-yne

Đáp án

Bài 11. Give IUPAC names for the following compounds.

Đáp án
Nội dung 2: Cho chất nền A, hỏi sản phẩm là gì nếu cho phản ứng với các tác chất khác
nhau.

Bài 1. For each of the following transformations, predict the major product and draw a mechanism
for its formation:

Đáp án

Bài 2. Draw the major product expected from each of the following reactions:

Đáp án

a) b)

Bài 3. Draw the major product expected when each of the following alkynes is treated with
sodium in liquid ammonia (Na/NH3):
Đáp án

a) b) c) d)

Bài 4. Predict the major product(s) expected for each of the following reactions:

Đáp án

a) b)

c) d)

e) f)

Bài 5. Draw the major product(s) expected when each of the following alkynes is treated with
aqueous acid in the presence of mercuric sulfate (HgSO4):
Đáp án

a) b)

c) d)

Bài 6. Draw the major product for each of the following reactions:
Đáp án
a)

b)

c)

Bài 7. Draw the major products that are expected when each of the following alkynes is treated
with O3 followed by H2O:
Đáp án

a) b)

c) d)

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

Đáp án
Bài 9. Predict the products obtained when 1-pentyne reacts with each of the following reagents:
(a) H2SO4, H2O, HgSO4 (b) R2BH followed by H2O2, NaOH
(c) Two equivalents of HBr (d) One equivalent of HCl
(e) Two equivalents of Br2 in CCl4 (f) NaNH2 in NH3 followed by MeI
(g) H2, Pt

Đáp án

a) b)

c) d)

e) f)

g)
Bài 10. Predict the final product(s) for each sequence of reactions:

Đáp án

a) b)

c) d)