Chem 22
Homework set 1
End-of-chapter problems from Hornback: Ch 5: 25, 27, 28, 31, 32, 35. You can work the
following "backward" (i.e. go from the name in the SG to the structure): 24, 30, 33; Ch 12: All
problems contain a mixture of nomenclature that we're not covering and some that we are.
1. Draw the following compounds. Show stereochemistry as appropriate. Pay particular
attention to the presence or absence of the prefix cyclo-. The ratio of resulting frustration to ease
of correction (let's call this the F/C ratio) is very high for this, EH? (that's Canadian for "EH?")
alcohols —
(a) (R)-5-methyl-3-hexanol
(b) (S)-1,2-pentanediol
(c) trans-3-hexen-1-ol
(d) (S)-2-cyclobutenol
(e) 2-methyl-4-pentyn-2-ol
ethers —
(f) (E)-1-ethoxy-2-bromopropene
(g) cis-1-methoxy-3-methylcyclobutane
(h) (S)-4-isopropoxy-2-hexyne
amines —
(i) (R)-3-heptanamine
(j) N-ethylcyclobutanamine
(k) N,N-dimethyl-3-buten-1-amine
aromatic compounds —
(l) p-vinylphenol
(m) o-tert-butoxyaniline
(n) 3,4-dichlorotoluene
(o) trans-4-isopropyl-1-(p-methoxyphenyl)cyclohexane
ketones —
(p) 4-methyl-2-pentanone
(q) 1-pentyn-3-one
(r) 1,3-cyclohexanedione
(s) (Z)-4-phenyl-3-buten-2-one
aldehydes —
(t) m-(bromomethyl)benzaldehyde
(u) (Z)-3-heptenal
(v) butanedial
(w) 1-cyclopropenecarbaldehyde
(x) Please check that you didn't make the cyclo-/not mistake. Please. 2. Organic chemists often use common names instead of Official Systematic IUPAC Names for
simple compounds. You should be able to figure these out...
(a)
(b)
(c)
(d)
(e)
(f)
(g)
diphenyl ether
tributyl amine
benzyl chloride
isopropyl alcohol
methyl tert-butyl ether
methyl ethyl ketone
trimethylammonium chloride
3. Here's a little chemistry review...
(a) Phenol has a pKa of 10. Write the acid-base reaction of phenol and NaOH. Which
way does the equilibrium lie? What is Keq? What is ΔG°?
(b) Anilinium ion (the conjugate acid of aniline) has a pKa of about 5. Write the acidbase reaction of aniline and aqueous hydrochloric acid. Which way does the equilibrium lie?
What is Keq? What is ΔG°?
(c) Draw the two chair conformations of the compound in prob #1, part o. Which is
more stable?
(d) Draw all of the stereoisomers of 3-hepten-5-yne-2-ol.
(e) Ozonolysis is a fun and unique reaction that you probably remember from last
semester. Draw the alkenes that would produce the following compounds upon treatment with
ozone followed by dimethylsulfide.
(i) 2-pentanone and propanal
(ii) 3-ethylhexanedial
(iii) benzaldehyde (only product)
(f) The nitro group of nitrobenzene, Ph–NO2, cannot be properly described by a single
Lewis structure. Draw the resonance structures that make up the "first-order" description of
nitrobenzene. Then there are several minor resonance contributors that account for the wee bits
of positive charge on the Cs ortho and para to the NO2 group. Draw these.
(g) Here's a quick prelude to Monday's discussion section. How many different 1H NMR
signals would you expect for the following molecules? (i.e., we don't see a distinct signal for
every single H because some of these are equivalent by symmertry. So how many Hs or sets of
equivalent Hs are there?)
(i) 1-hexanol
(ii) 1-hexene
(iii) 1,1-dimethylcyclopentane
(iv) 2-ethoxypropane Chem 22
Spring 2010
Name _________________________________________
HW set 1
15 points; due Fri, Jan 29 at the beginning of class.
1. Draw.
(a) (R)-3-phenoxy-2-cyclopentenol
(b) m-propyl-N-cyclopropylaniline
(c) (S)-3-ethoxycyclohexanone in its most stable conformation. (It will much easier to draw if
you put the carbonyl group at the extreme left or right of the chair.)
(d) (E)-4-chloro-4,6-heptadienal
(e) 4-(1-cyclobutenyl)-1-(p-nitrophenyl)-3-butyn-2-one
Chemistry 22 Homework set 1
of 3
Report
Tell us what’s wrong with it:
Thanks, got it!
We will moderate it soon!
Free up your schedule!
Our EduBirdie Experts Are Here for You 24/7! Just fill out a form and let us know how we can assist you.
Take 5 seconds to unlock
Enter your email below and get instant access to your document