CHEM 135

Exam No. 2
Oct. 20, 2015

KEY
_________________________________________

Name 100 points total

1. (21) Write structural formulas for the major organic product(s) for the following reactions. Be
sure to indicate the stereochemistry when relevant.

(a)

(b)
(c)
(d)

2. (12) Arrange the following in order of:

(i)

Increasing acidity

______c________
least acidic

_______a_______

_______b______

________d______
most acidic

(ii)

increasing reactivity with HBr.

(iii)

increasing wavelength for the HOMO to LUMO transition in the UV-Visible spectrum.

3. (8) Sketch the approximate structure of the following intermediates and transition states. Be sure to indicate
formal charge, partial charge distribution, and partial bonds.
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(a) The lowest energy intermediate in the reaction of HI with 3-methyl-1butene.

(b) The transition state for the second step in the reaction of propene with Br2/CH2Cl

4. (8) (a) Propose a mechanism for the following reaction (Show all curved arrows);

(b) Which step is the rate-determining step? Step 1

(c) Which step is the rate-determining step? The alcohol oxygen

5. (5) Name the following compound using the IUPAC nomenclature system.
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Z-2-bromo-6-chloro-5-isopropyl-3-methyl-2-undecen-8-yne

6. (8) 1-phenyl-1,3-butadiene can conceivably give several products when reacted with HCl,
however, only two products predominate. Write a mechanism for this reaction that shows
the two products and how they are formed. Which product is favored under kinetically
controlled conditions and which is favored under thermodynamically controlled
conditions? Explain.

1,2-addition

1,4-addition

kinetic - proximetry effect

thermodynamic - more stable conjugated alkene

7. (16) Draw three important contributing resonance structures for each of the following molecules and
ions. Show all electrons including non-bonding and bonding pairs and indicate formal charges.
Indicate which resonance form would contribute the most and which would contribute least to
each of the resonance hybrids

8. (6) Indicate which of the following molecules and ions would show aromatic character. For those
that are aromatic indicate the number of pi electrons in the system and for those that are not give
a reason why.

9. (10) Outline a sequence of reactions suitable for preparing the following two compounds from
the indicated starting materials. You may use any necessary organic or inorganic reagents.

10. (6) IR spectra for three of the following compounds are given below. Match the spectra with
the most likely compound.

i
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