TUTORIAL 4

1. Outline all the steps in the synthesis of propyne from the following substrate structure
CH3COCH3
2. Acid-catalyzed dehydration of neopentyl alcohol ((CH3)3CCH2OH) yields 2-methyl-2-butene as a
major product. Provide a full mechanism showing all steps involved in the formation of the product.
3. Consider the reaction below and draw a full labeled free-energy diagram for the hydrogenation of an
alkene in the presence of a catalyst and the hypothetical reaction in the absence of a catalyst.
R

H
C

R
(a)4.

+ H2

OH

Br

CH2

+ heat

Outline ALL steps for the synthesis of the following compound from the given starting material. Use
any other reagents of your choice.

(4)

Br

OH

5.
Propose a mechanism for each
of the reactions shown.
(c)
from
(a) (CH3)2CHCH=CH2 + HCl (CH3)2CClCH2CH3
6. Fill the missing reagents
(d)

(3)

from

from
(b)

CH2

(CH3)3 CBr

from

(CH3)2CHCH2OH

(5)

(3)

(b) Propose syntheses for the following molecules from an alkyl halide or sulfonate ester. X = Cl, Br
or OMs, OTs. You can substitute X with any of these leaving groups. Please note that they are all
good leaving groups.