14.47 What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible, indicate which you expect to be major. the ring Draw th CH, (b) CH,CH,CH,CCH, CH3 (a) 14.54 The boi of eithe (e) H,C- -CH, (d) -CHCH,CH, though 14.55 Propan roethar OH STEREOCHEMI (e) CH,CH,CCH,CH, 14.56 Define (n) Ch

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Chapter8: Haloalkanes, Halogenation, And Radical Reactions
Section: Chapter Questions
Problem 8.11P
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of either ethanethiol (37 °C) or chloroethane (13 C), ev
though all three compounds have similar MWs. Explain.
14.55 Propanol is very soluble in water, but ethanethiol snd de.
Draw the starting compound in line structure formal les,
the ring. Draw the structure of this cyclic disulide (Hin
14.54 The boiling point of propanol is 97 °C, much higher than t
472
CHAPTER 14 Some Compounds with Oxygen, Sulfur, or a Halogen
1447 What alkenes might be formed by dehydration of the
following alcohols? If more than one product is possible,
indicate which you expect to be major.
CH,CHCH,CH,CHCH,
CH3
SH
2,5-Hexanedithiol
SH
(a)
(b) CH,CH,CH,CCH,
HO,
ÓH
(e) H,C-
-CH, (d)
CHCH,CH,
OH
roethane are only slightly soluble. Explain.
STEREOCHEMISTRY AND CHIRALITY (SECTION 14.10)
(e) CH,CH,CCH,CH3
14.56 Define the following terms:
ČH,CH3
(a) Chiral
(b) Achiral
(c) Chiral carbon
(d) Enantiomer
3449 What carbonyl-containing products would you obtain from
the oxidation of the following alcohols? If no reaction
14.57) Are the following items chiral or achiral? Give a jusife
tion for your answers.
occurs, write "NR."
OH
(a) A fork
(b) This textbook
-CH,CH2
(c) Your right hand
(b) CH,CH,CHOH
ČH,
(d) A blank 3 x 5 index card
14.58 identify the chiral center(s) in each of the following
molecules:
но
CH
(a) 2-Methyl-3-pentanol
OH
(b) 3-Chloro-l-butand
(c) 2,3-Pentanediol
(d)
(c)
(d)
OH
OH
(e)
(1)
CHCH,CH,
OH
OH
two chiral centers
two chiral centers
14.49 What alcohols would you oxidize to obtain the following
carbonyl compounds?
14.59 Are the following molecules chiral or achiral? If they arn
chiral, identify the chiral carbon atom(s).
(a) 3-Pentanol
(e) 2-Methylcyclohexanol
H,C
(b) 2-Bromobutane
(a)
(b)
CHCH,COH
(d)
CH3
(c) CH,CH,CHCH,ÖCH,CH,
OH
URLOI uD DICU FIDES (CECTION 140)
Transcribed Image Text:of either ethanethiol (37 °C) or chloroethane (13 C), ev though all three compounds have similar MWs. Explain. 14.55 Propanol is very soluble in water, but ethanethiol snd de. Draw the starting compound in line structure formal les, the ring. Draw the structure of this cyclic disulide (Hin 14.54 The boiling point of propanol is 97 °C, much higher than t 472 CHAPTER 14 Some Compounds with Oxygen, Sulfur, or a Halogen 1447 What alkenes might be formed by dehydration of the following alcohols? If more than one product is possible, indicate which you expect to be major. CH,CHCH,CH,CHCH, CH3 SH 2,5-Hexanedithiol SH (a) (b) CH,CH,CH,CCH, HO, ÓH (e) H,C- -CH, (d) CHCH,CH, OH roethane are only slightly soluble. Explain. STEREOCHEMISTRY AND CHIRALITY (SECTION 14.10) (e) CH,CH,CCH,CH3 14.56 Define the following terms: ČH,CH3 (a) Chiral (b) Achiral (c) Chiral carbon (d) Enantiomer 3449 What carbonyl-containing products would you obtain from the oxidation of the following alcohols? If no reaction 14.57) Are the following items chiral or achiral? Give a jusife tion for your answers. occurs, write "NR." OH (a) A fork (b) This textbook -CH,CH2 (c) Your right hand (b) CH,CH,CHOH ČH, (d) A blank 3 x 5 index card 14.58 identify the chiral center(s) in each of the following molecules: но CH (a) 2-Methyl-3-pentanol OH (b) 3-Chloro-l-butand (c) 2,3-Pentanediol (d) (c) (d) OH OH (e) (1) CHCH,CH, OH OH two chiral centers two chiral centers 14.49 What alcohols would you oxidize to obtain the following carbonyl compounds? 14.59 Are the following molecules chiral or achiral? If they arn chiral, identify the chiral carbon atom(s). (a) 3-Pentanol (e) 2-Methylcyclohexanol H,C (b) 2-Bromobutane (a) (b) CHCH,COH (d) CH3 (c) CH,CH,CHCH,ÖCH,CH, OH URLOI uD DICU FIDES (CECTION 140)
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