8.32 Show how 1-hexyne could be synthesized from each of the following: (a) 1-Hexene (b) 1-Chlorohexane (c) 1-Chloro-1-hexene (d) 1,1-Dichlorohexane (e) Propyne and propyl bromide
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- Identify the compound in each of the following pairs that reacts more rapidly in SN2 reactions: (a) 1-bromopentane or 3-bromopentane (b) 2-chloropentane or 2-fluoropentane (c) 2-bromopropane or 1-bromohexane (d) 1-chlorohexane or cyclohexyl chlorideWhich compounds can be prepared in high yield by halogenation of an alkane? (a) 2-Chloropentane (b) Chlorocyclopentane (c) 2-Bromo-2-methylheptane (d) (R)-2-Bromo-3-methylbutane (e) 2-Bromo-2,4-trimethylpentane (f) Iodoethane-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
- Assign E or Z stereochemistry to each of the following alkenes, and convert each drawing into a skeletal structure (red = 0, yellow-green = Cl). (a) (b)(a) Account for the following :(i) Electrophilic substitution reactions in haloarenes occur slowly.(ii) Haloalkanes, though polar, are insoluble in water.(b) Arrange the following compounds in increasing order of reactivity towards SN2 displacement:2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentane2. How would you prepare the following substances from 2-cyclohexenone? More than one step may be needed. (a) Cyclohexene (b) 3-Phynylcyclohexanone (c) 3-Oxocyclohenanecarboxylic acid (d) Methyleyclohexane
- Specify reagents suitable for converting 3-ethyl-2-pentene to each of the following: (a) 2,3-Dibromo-3-ethylpentane (b) 3-Chloro-3-ethylpentane (c) 3-Ethyl-3-pentanol (d) 3-Ethyl-2-pentanol (e) 2,3-Epoxy-3-ethylpentane (f) 3-EthylpentaneCompound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughoutArrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3
- Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.Write structural formulas for the products that form when 1-butene reacts with each of the following reagents: (a) HI (b) H2, Pt (c) Dilute H2SO4, warm (d) Cold concentrated H2SO4 (e) Cold concentrated H2SO4, then H2O and heat (f) HBr (g) Br2 in CCl4 (h) Br2 in H2O (i) HCl (j) O3, then Me2S (k) OsO4, then NaHSO3/H2O (l) KMnO4, OH-, heat, then H3O+ (m) Hg(OAc)2 in THF and H2O, then NaBH4, OH- (n) BH3:THF, then H2O2, OH-Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibro- mide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. CH3 CH3 CH3 Br Br CH,Cl, + Br2 or Br Br (a) (b) Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?