This preview has intentionally blurred sections. Sign up to view the full version.View Full Document
Unformatted text preview: / CHEMISTRY HTK ASSIGNMENT 5 V 1. Write equations that describe reactions which could be used to prepare l-bromopropane from: a) propan- l —01
c) propane Remember to specify necessary reagents and reaction conditions. Write equations to show the substitution reactions of 1-bromopropane with: a)
f) a) b) d) aqueous sodium hydroxide
ammonia potassium cyanide
benzene aminomethane Which of the following compounds would react most quickly with sodium iodide in
acetone? i) bromobenzene
iv) 2-bromo-2-butene Write the complete mechanism for the reaction you chose, identifying the substrate and
the leaving group. Draw a potential energy diagram for the reaction and a 3D structure of the transition state.
Which of the following reagents would react faster with l-bromobutane? i) sodium iodide / alcohol
ii) sodium chloride / alcohol A compound containing Mammmmmwmmmer, but dig
not mix with it. When warmed with dinhxdmxidﬂolmion, the liquid dissolved
and the resulting mixture formed a cream to very pale yellow precipitate..mith.§ih&€1nitmle solution. Wlﬂl the original li_quid was boiled with althDliQmLassinmhydmxide, agas which decolourized bromine solution was evolved. Identify the substances used and
explain the chemistry involved, writing equations for all reactions which occurred. b) Describe the NMR spectra expected from the organic substances used or formed during the reactions. TURN OVER Q? Propose good syntheses for the following compounds starting from 3-methy1butan—1-ol: a) 2-methyl-1-butanthiol , (CH3)2CHCH2CHZSH
c) 3-methy1- l—butene
Outline syntheses of the following compounds from l—bromobutane:
a) butane b) octane c) but-l-ene
(D d) cis—but—Z-ene e) trans-but-Z-ene . f) l-butyne
g) 3-octyne h) _2-bromobutane i) pentanenitrile
j) n—butyl phenyl ether
Write mechanisms for all steps in part ((1) and (j). 093’» ‘
Some l-iodo—Z-methylheptane was mixed with sodium amide, NaNH2 in ether in order to prepare the corresponding amine, l-amino-Z—methylheptane. A good yield of a liquid
c m ound with the followin IR. 5 ctrum wa ai (1, Explain this observation, by analyzing the spectrum and writing a mechanism for the reaction which occurred. I FREQUENCY (CM-ll
1800 1600 TRANSMITTANCE (x) IR PHASE
NMR SOLVENT ma.
m S m
0 F: 7
m s T e,
W e nNU M
m. m m
m m 6
W m m 00
d m1 3
m , mam.
m M :7,B,
w W U m m6.8.
e ‘ m 6 51L.
an... M R .Dln w 0 MHZ
W U U C a m6.8.
.n R E e P95
.10. E S T a .w , a
D: S A x .H w
. 5 Dn .S D c M 3
8 M A m A ..
U n , ...
View Full Document
- Spring '08
- Organic chemistry