TUTORIAL 2

Chapter 2
Organohalides
2.1 Naming alkyl halides
2.2 Structure of alkyl halides
2.3 Preparing alkyl halides from alkanes and alkenes
2.4 Reaction of alkyl halides
________________________________________________________________________________
1. Gie the name for each of the follo!ing alkyl halides.
"#$3

"#2"l2
2. %ra! structures corresponding to these names.
3&iodopropene
trans&1&chloro&3&sec&'utylcyclohe(ane
1)2&dichloro&1)1)2)2&tetrafluoroethane
3. *o ans!er the follo!ing +uestions consider the reaction 'elo!,
*he reaction of propyl'en-ene !ith tert&'utylhypochlorite proceeds 'y a radical su'stitution
path!ay. %ra! the structure of the radical intermediate leading to each product.
H C
Cl
C
Cl
Cl
H
H
F C
F
C
F
Cl
H
Br
Cl
Cl
Cl
(CH
3
)
3
COCl
40
0
C
+ +
65% 25% 10%
4. "onsider the reaction 'elo! to ans!er the follo!ing +uestions.
%ra! all the monochlorination products of methylcyclopentane .ignore stereoisomers/.
0. "onsider the reaction 'elo! to ans!er the follo!ing +uestions.
Place asterisks.1/ at all allylic positions in compound A.
%ra! the resonance forms of the allylic radical intermediate that accounts
for the formation of B and C.
2. "hoose the best reagent or se+uence of reagents from the list proided 'elo! for carrying out the
follo!ing transformations. Place the letter of your response to the left of the reaction.

CH
3
Cl
2
light
OH Cl
CH
3
CHCH CHCH
2
CH
3
Br
CH
3
CH CHCHCH
2
CH
3
Br
CH
3
CH CHCH
2
CH
2
CH
3
NBS
C B A
+
hv
CH
3
C H
3
C
CH
3
Br
CH
3
C H
3
C
CH
3
OH
3. Predict the best reagent or se+uence of reagents for carrying out the follo!ing transformations.
4. Propose a synthesis of each of the follo!ing compounds from the gien starting material and any
inorganic reagents necessary.
5. $dentify the reagents a and b in the follo!ing scheme.
NBS
CCl
4
+
HCl
ether
Cl
1. NBS, CCl
4
2. KOH, ethanl
!Br
3
ether
Br
CH
3
CHCH CH
2
CH
3
CH
3
CHCH
2
CH
2
OH
CH
3
"r#
16. "ircle your response in each set 'elo!.
i. *he least reactie compound in an SN2 reaction.
ii. *he least reactie compound in a SN1 reaction.
iii. *he best solent for an SN2 reaction.
11. Cn$i%er the rea&tin 'el( t an$(er the "ll(ing )*e$tin$.
+rite the &#,lete $te,(i$e #e&hani$# "r thi$ rea&tin. Clearl- $h( the "r#atin " 'th ,r%*&t$. Sh(
all ele&trn "l( (ith arr($ an% %ra( all inter#e%iate $tr*&t*re$.
Br
a b
CH
2
.
H .
CH
3
CH
2
O/$
H Br
(CH
3
)
3
C . !hCHCH
3
Br
CH
3
CHCH
3
F
Cl

H0!1
CHCl
3
H
2
O CH
3
CH
2
OH
H
3
C Cl
H
3
C OH
HO CH
3
40%
60%
H
2
O
ethanl
+