Download NaOH + CH3Cl CH3OH + NaCl

HWeb13 (Chapter 6.1-6.8)
13.1.
In the following reaction, what is the leaving group?
NaOH
+
CH3Cl
CH3OH
+
NaCl
[a]. sodium
[b]. chloride
[c]. hydroxide ion
[d]. chloromethane
13.2
Which of the following are nucleophilic?
A methanol
B bromide anion
C hexane, CH3(CH2)4CH3
D hydronium ion, H3O+
[a]. only A
[b]. only A and B
[c]. only B and D
[d]. A, B, C and D
13.3.
What is the effect of doubling the concentration of sodium bromide on the following SN2 reaction?
CH3Cl + NaBr → CH3Br + NaCl
[a]. The rate of the reaction doubles
[b]. The rate constant, k, doubles
[c]. The product changes
[d]. Nothing
HWeb14 (Chapter 6.13-6.14; 4.17; 7.10-7.12)
14.1.
Which of the following reacts the fastest in an SN2 reaction with sodium methoxide?
[a]. 1-bromobutane
[b]. 2-chlorobutane
[c]. isopropyl fluoride
[d]. 2-chloro-2-methylpropane
14.2.
Which of the following is a polar aprotic solvent?
[a]. water
[b]. acetic acid
[c]. pentane
[d]. N,N-dimethyl formamide
14.3.
Which of the following is the most nucleophilic in ethanol?
[a]. fluoride anion
[b]. chloride anion
[c]. bromide anion
[d]. iodide anion
HWeb15 (6.9-6.13, 6.15)
15.1.
Which of the following halides undergoes the most rapid SN1 reaction with water?
Br
1
Br
Br
2
3
Cl
4
[a]. 1
[b]. 2
[c]. 3
[d]. 4
15.2.
What is the reactive intermediate in an SN1 reaction of tert-butyl chloride and water?
[a]. a tert-butyl carbocation
[b]. 2-methylpropane
[c]. a tert-butyl radical
[d]. a tert-butyl carbocation
15.3.
Which of the following carbocations is the most stable?
A
1. A
[b]. B
[c]. C
[d]. D
B
C
D
HWeb16 (11.6-11.12)
16.1.
Which of the following reagents does not convert primary alcohols into alkyl halides?
[a]. HI
[b]. SOCl2
[c]. KBr
[d]. PBr3
16.2.
What is the product of the reaction between (S)-2-pentanol with tosyl chloride followed by reaction
with sodium cyanide?
[a]. (S)-2-cyanopentane
[b]. (R)-2-cyanopentane
[c]. racemic 2-cyanopentane
[d]. cyanotosylate
16.3.
Which of the following ethers cannot be made by a Williamson ether synthesis
[a]. A
[b]. B
[c]. C
[d]. D
HWeb17 (4.18-4.19 + review)
17.1.
Why is sodium amide chosen to deprotonate terminal acetylenes prior to alkylation?
[a]. Sodium amide is a good nucleophile
[b]. Sodium amide is a very strong base
[c]. Sodium amide is a polar aprotic solvent
[d]. Sodium amide is a Lewis acid
17.2.
Treatment of ethyne with sodium amide followed by reaction with 1-bromobutane gives compound
X. Treatment of X with sodium amide followed by 1-bromo-3-methylbutane gives compound Y?
Catalytic hydrogenation (H2/Pt) of Y gives Z. What is the IUPAC name of Z?
[a]. 2-methyldecane
[b]. 3-methyldecane
[c]. 4-methyldecane
[d]. 5-methyldecane
17.3.
Which of the following would be a suitable solvent for the depotonation of 1-propyne by sodium
amide?
[a]. acetic acid
[b]. ammonia
[c]. water
[d]. methanol
HWeb18 (Review of Topic 6)
18.1
Which of the following is the best leaving group in the solvolysis of tert-butyl halides?
[a]. fluoride
[b]. chloride
[c]. bromide
[d]. iodide
18.2
Which of the following best describes the hydrolysis of tert-butyl bromide?
[a]. a rapid heterolytic cleavage of the C-Br bond to give a tert-butyl carbocation and bomide anion,
followed by slow nucleophilic attack of water on the carbocation
[b]. a slow homolytic cleavage of the C-Br bond to give a tert-butyl radical and bromine atom (a
radical), followed by slow nucleophilic attack of water on the radical
[c]. a slow heterolytic cleavage of the C-Br bond to give a tert-butyl carbocation and bromide anion,
followed by rapid nucleophilic attack of water on the carbocation
[d]. a rapid nucleophilic attack of water on tert-butyl bromide with concerted cleavage of the C-Br
bond.
18.3
Which of the following halides undergoes the most rapid substitution reaction with water?
[a]. 1
[b]. 2
[c]. 3
[d]. 4