Chapter 9: Q18P (page 482)
Show how hex-1-yne might be converted to
(a) 1,2-dichlorohex-1-ene. (b) 1-bromohex-1-ene.
(c) 2-bromohex-1-ene. (d) 1,1,2,2-tetrabromohexane.
(e) 2-bromohexane. (f) 2,2-dibromohexane.
Short Answer
(a)

(b)

(c)

(d)

(e)

(f)

Chapter 9: Q18P (page 482)
Show how hex-1-yne might be converted to
(a) 1,2-dichlorohex-1-ene. (b) 1-bromohex-1-ene.
(c) 2-bromohex-1-ene. (d) 1,1,2,2-tetrabromohexane.
(e) 2-bromohexane. (f) 2,2-dibromohexane.
(a)

(b)

(c)

(d)

(e)

(f)

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Write structural formulas for the following compounds (includes both old- and new-style names).
(a) 2-octyne (b) ethyl isopentyl acetylene (c) ethynylbenzene
(d) cyclohexyl acetylene (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
The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.
Deduce the structure of each compound from the information given. All unknown in this problem have molecular formula C8H12.
(a)Upon catalytic hydrogenation, unknown Wgives 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 Xgives cyclooctane. Ozonolysis of X,followed by reduction with dimethyl sulfide, gives two equivalents of butanedial , O =CH -CH2 CH 2-CH = O. Draw the structure of X.
(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, 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 reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO ) group on C1 and a one-carbon aldehyde (CHO) group on C2. Draw the structure of Z.
Question: Predict the products of the following acid-base reactions, or indicate if no significant reaction would take place.
The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.
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