CHEM 219 MODULE 5 COMPREHENSIVE
STUDY GUIDE 2026 FULL QUESTIONS AND
SOLUTIONS GRADED A+
◍ Cyanide ion.
Answer: If this nucleophile is added to an aldehyde or ketone an
Cyanohydrin results
◍ Order of ease of dehydration of alcohol substrates....
Answer: 3>2>1 Tertiary require the least harsh conditions (typically 25%
aqueous acid and 60-80 degrees C) whereas primary require fully
concentrated acid and temperatures approaching 200 degrees C.
◍ A. acid halide
B. Ester
C. Carboxylic acid
D. Carboxylic acid (or ester)
E. Carboxylic acid.
Answer: Complete the following table (provide answers for a-e) to predict
the outcome of the indicated reactions of carboxylic acids and their
derivatives
◍ Alcohols Acidity/Basicity.
Answer: Can act as a weak base (accepting H+ using a lone pair on the O
atom) or weak acid (donating the O-H proton as H+)
◍ Oxidizing agents that convert alcohols to Carbonyl compounds.
Answer: Potassium Permanganate (KMnO4)Sodium Hypochlorite (NaOCl)
◍ 3,5-dinitrophenol.
Answer: Name the following alcohol using IUPAC systematic nomenclature
, ◍ a) a diol b) a hemiacetal c) an imine d) a cyanohydrin.
Answer: Complete the following table describing the various types of
nucleophilic additions to the C=O of aldehydes and ketones.
◍ Conversion using Thionyl Chloride (SOCl2).
Answer: Alcohol (R-OH) + Thionyl Chloride (Cl-S=O-Cl) —> alkyl
Chloride (R-Cl) + SO2 ^ + HCl- very efficient with primary and secondary
alcohols d/t the main byproduct (SO2) beig formed as a gas and leaving the
reaction mixture.
◍ Conversion using Phosphorous Halides (PX3).
Answer: X= Cl or Br- Alcohol (3R-OH) + phosphorous trihalide (X2P-X)
—> alkyl halide (3R-X) + H3PO3-particularly efficient as one molecule of
PX3 can convert 3 molecules of alcohol to the corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
◍ Synthesis of expoxides from alkenes.
Answer: Use peracid (peroxyacid). Forms by transfer of the extra O to the
alkene. C=C bond is broken and incorporates the O atom as a part of a 3
membered ring.
◍ Williamson Synthesis.
Answer: Two steps to produce an asymmetric ether, in fist step alcohol is
converted to its conjugate base, (Alkoxide ion RO-) by reacting the alcohol
with sodium or potassium metal. The Alkoxide is then reacted as a
nucleophile in an Sn2 displacement, typically on an alkyl halide substrate.
Net result is an ether where R does not equal R. Typically primary or
secondary only.
◍ cyclopropanol.
Answer: Name the following alcohol using IUPAC systematic nomenclature
◍ If more than one alkene product is possible....
Answer: The major product is the one whose C=C has more alkyl groups
attached.
◍ Secondary Alcohols react via... (with HX).
STUDY GUIDE 2026 FULL QUESTIONS AND
SOLUTIONS GRADED A+
◍ Cyanide ion.
Answer: If this nucleophile is added to an aldehyde or ketone an
Cyanohydrin results
◍ Order of ease of dehydration of alcohol substrates....
Answer: 3>2>1 Tertiary require the least harsh conditions (typically 25%
aqueous acid and 60-80 degrees C) whereas primary require fully
concentrated acid and temperatures approaching 200 degrees C.
◍ A. acid halide
B. Ester
C. Carboxylic acid
D. Carboxylic acid (or ester)
E. Carboxylic acid.
Answer: Complete the following table (provide answers for a-e) to predict
the outcome of the indicated reactions of carboxylic acids and their
derivatives
◍ Alcohols Acidity/Basicity.
Answer: Can act as a weak base (accepting H+ using a lone pair on the O
atom) or weak acid (donating the O-H proton as H+)
◍ Oxidizing agents that convert alcohols to Carbonyl compounds.
Answer: Potassium Permanganate (KMnO4)Sodium Hypochlorite (NaOCl)
◍ 3,5-dinitrophenol.
Answer: Name the following alcohol using IUPAC systematic nomenclature
, ◍ a) a diol b) a hemiacetal c) an imine d) a cyanohydrin.
Answer: Complete the following table describing the various types of
nucleophilic additions to the C=O of aldehydes and ketones.
◍ Conversion using Thionyl Chloride (SOCl2).
Answer: Alcohol (R-OH) + Thionyl Chloride (Cl-S=O-Cl) —> alkyl
Chloride (R-Cl) + SO2 ^ + HCl- very efficient with primary and secondary
alcohols d/t the main byproduct (SO2) beig formed as a gas and leaving the
reaction mixture.
◍ Conversion using Phosphorous Halides (PX3).
Answer: X= Cl or Br- Alcohol (3R-OH) + phosphorous trihalide (X2P-X)
—> alkyl halide (3R-X) + H3PO3-particularly efficient as one molecule of
PX3 can convert 3 molecules of alcohol to the corresponding alkyl halide
-byproduct of the reaction is phosphorous acid
◍ Synthesis of expoxides from alkenes.
Answer: Use peracid (peroxyacid). Forms by transfer of the extra O to the
alkene. C=C bond is broken and incorporates the O atom as a part of a 3
membered ring.
◍ Williamson Synthesis.
Answer: Two steps to produce an asymmetric ether, in fist step alcohol is
converted to its conjugate base, (Alkoxide ion RO-) by reacting the alcohol
with sodium or potassium metal. The Alkoxide is then reacted as a
nucleophile in an Sn2 displacement, typically on an alkyl halide substrate.
Net result is an ether where R does not equal R. Typically primary or
secondary only.
◍ cyclopropanol.
Answer: Name the following alcohol using IUPAC systematic nomenclature
◍ If more than one alkene product is possible....
Answer: The major product is the one whose C=C has more alkyl groups
attached.
◍ Secondary Alcohols react via... (with HX).
