Winning Fifty Points
Revision
430 Chem.
What is the IUPAC name for
(CH3)3CCH(OH)CH2CH(OH)CH2CH(CH3)2?
A) 1,1,1,6-tetramethyl-2,4-heptanediol
B) 2,2,7-trimethyl-3,5-octanediol
C) 2,2,6,6-tetramethyl-3,5-heptanediol
D) 2,7,7-trimethyl-4,6-octanediol
Which of the following reagents would you expect to
react with bromocyclopentane by an SN2 mechanism?
A) C2H5OH
B) C2H5O(-) K(+)
C) NaCN
D) (CH3)3N
Compound X (C6H12) reacts with HI. The product of this reaction,
when treated with KOH in ethanol, gives Y ( an isomer of X ).
Ozonolysis of X (H2O2 workup) produces two compounds: a two
carbon Aldehyde, and a four carbon ketone. What is X?
A) 2-methyl-2-pentene
B) 4-methyl-1-pentene
C) 2,3-dimethyl-2-butene
D) 3-methyl-1-pentene
Which one of the following alcohols will be oxidized
by (CrO3 in 50% sulphuric acid) to a ketone having
the same number of carbon atoms ?
A) 1-methylcyclohexanol
B) 3,3-dimethylcyclopentanol
C) 3-methyl-1-hexanol
D) 3-ethyl-3-hexanol
Which reagent(s) would best accomplish the following
transformation
A) H3O+ & heat
B) (i) HgSO4 in H2O (ii) NaBH4
C) (i) B2H6 in ether (ii) H2O2 and base
D) (i) HOBr (ii) Mg in ether
Which of the following reagents would not effect the
following transformation?
A) HCl & ZnCl2
B) PCl3
C) SOCl2
D) KCl (5 molar solution)
A C7H13Br compound reacts with KOH in ethanol to form 3methylcyclohexene as the major product.
What is a likely structure for the starting alkyl bromide?
A) cis-4-methylcyclohexyl bromide
B) trans-3-methylcyclohexyl bromide
C) cis-2-methylcyclohexyl bromide
D) trans-2-methylcyclohexyl bromide
Synthesis of hexane-3,4-diol from trans-3-hexene may be
accomplished in two ways:
(i) OsO4 hydroxylation & (ii) C6H5CO3H epoxidation followed by
NaOH opening of the epoxide ring.
Which of the following statements about the products from these
reactions is correct?
A) the two methods give the same product
B) (i) gives a chiral isomer, (ii) gives an achiral
isomer
C) (i) gives an achiral isomer, (ii) gives a chiral
isomer
D) two different isomers are formed, but both
are chiral
Which of the following reaction sequences
would best serve to convert 2-methyl-1bromopropane to 4-methyl-1-iodopentane?
A) (i) Mg in ether; .(ii) ethylene oxide (C2H4O);
(iii) HI & heat
B) (i) NaC≡CH in ether; .(ii) H2 + Lindlar catalyst;
(iii) HI
C) (i) KOH in alcohol; . (ii) C6H5CO3H in CH2Cl2;
(iii) NaC≡CH in ether ; (iv) 2 H2 + Pt catalyst
D) (i) NaC≡CH in ether; .(ii) H3O+ + HgSO4;
(iii) HI & heat
Which of the following reagents would be
best for oxidizing a 1º-alcohol to an
aldehyde?
A) H3PO4
B) POCl3 in CH2Cl2
C) Jones' reagent (H2CrO4))or
orKMnO
KMnO44// HH++
D) OsO4