Aldehydes & Ketones Questions

Treatment with O₃, followed by dimethyl sulfide (DMS), converts a trans-disubstituted alkene into a(n)
1. primary alcohol and aldehyde
2. allylic alcohol and ketone
3. secondary alcohol and carbon dioxide
4. tertiary alcohol and carboxylic acid
5. a

Organic Chemistry

Aldehydes & Ketones Solutions

Treatment with O₃, followed by dimethyl sulfide (DMS), converts a trans-disubstituted alkene into a(n) 1. primary alcohol and aldehyde 2. allylic alcohol and ketone 3. secondary alcohol and carbon dioxide 4. tertiary alcohol and carboxylic acid 5. aldehyde and aldehyde 6. ketone and ketone 7. aldehyde and carbon dioxide

2) Provide the major organic product(s) for each of the following reactions. You may ignore drawing
stereoisomers if formed. (0.5 pts each)
Stork
1)
NH
, HO, pH 6
a)
2)
3) H30*
1) NaOH, HẠO
b)
H
H
2) But-3-en-2-one
(provide structure for product)

Organic Chemistry

Aldehydes & Ketones Solutions

2) Provide the major organic product(s) for each of the following reactions. You may ignore drawing stereoisomers if formed. (0.5 pts each) Stork 1) NH , HO, pH 6 a) 2) 3) H30* 1) NaOH, HẠO b) H H 2) But-3-en-2-one (provide structure for product)

6. Draw the major products obtained in each of the following reactions, indicating stereochemistry where
appropriate. If no reaction is anticipated, write "no reaction."
I
heat
1. LDA, -78 °C
2.
H
3. H30*, heat

Organic Chemistry

Aldehydes & Ketones Solutions

6. Draw the major products obtained in each of the following reactions, indicating stereochemistry where appropriate. If no reaction is anticipated, write "no reaction." I heat 1. LDA, -78 °C 2. H 3. H30*, heat

4. How will you synthesize cyclohexanecarboxaldehyde (cyclohexylmethanal) from the following reagents? (There are no
restrictions on the reagents or the number of steps).
(a) Cyclohexanone
(b) Ethynylcyclohexane
(c) Methyl cyclohexylformate (Remember: Form

Organic Chemistry

Aldehydes & Ketones Solutions

4. How will you synthesize cyclohexanecarboxaldehyde (cyclohexylmethanal) from the following reagents? (There are no restrictions on the reagents or the number of steps). (a) Cyclohexanone (b) Ethynylcyclohexane (c) Methyl cyclohexylformate (Remember: Formic acid is the IUPAC recognized name for Methanoic acid) (d) Cyclohexanecarboxylic acid (Cyclohexylmethanoic acid) (e) Vinylcyclohexane (f) Cyanocyclohexane (g) Cyclohexene (h) Cyclohexylmethanol (1) (Dimethoxymethyl)cyclohexane () Bromocyclohexane and formaldehyde

1. Upon treatment with an acid, the following ketone can exist in two different erol forms. Please draw them in
the boxes provided below and label each as the kinetic or thermodynamic enol:
Holocionu. Al GluMet

Organic Chemistry

Aldehydes & Ketones Solutions

1. Upon treatment with an acid, the following ketone can exist in two different erol forms. Please draw them in the boxes provided below and label each as the kinetic or thermodynamic enol: Holocionu. Al GluMet

stjohns.instructure.com
sity
Mall - Jenna D. Charles - Outlook
Quiz: Quiz No. 19 - Chapter 19
Question 5
2 pts
The Robinson annulation reaction is shown below. Identify the missing reagent in the first step.
O
O
CH
CH
KOH, CH,OH
2
CHO Na"
CH3OH
O
0
A) CH C

Organic Chemistry

Aldehydes & Ketones Solutions

stjohns.instructure.com sity Mall - Jenna D. Charles - Outlook Quiz: Quiz No. 19 - Chapter 19 Question 5 2 pts The Robinson annulation reaction is shown below. Identify the missing reagent in the first step. O O CH CH KOH, CH,OH 2 CHO Na" CH3OH O 0 A) CH CH CHCH B) HỌC CHCCH O C) H C CHCH.CH D) CH3CCH2CH3 Compound C Compound D Compound B Compound A No new data to save. Last checked at 12:29pm Submit Quiz 888 11 $ & BOLO 5 7 8 E R T Y U o D F G H J K C V B. N. M

Ester undergoe Claisen condensation,
saponification, acidification, and
decarboxylation to give a ketone.
Can you propose another method for
transformation of an ester to a ketone (a, b, c)?
+
1. Et O' Na*
O Et
OEt
2. H2O, HCI
Claisen condensation
ri
3
3.

Organic Chemistry

Aldehydes & Ketones Solutions

Ester undergoe Claisen condensation, saponification, acidification, and decarboxylation to give a ketone. Can you propose another method for transformation of an ester to a ketone (a, b, c)? + 1. Et O' Na* O Et OEt 2. H2O, HCI Claisen condensation ri 3 3. NaOH, H2O, heat O Et 4. H2O, HCI Saponification e OH Boom.co 5. heat OH Decarboxylation + CO2

Mechs for q 4 Mech writer name
4. Which of the following could result from the dehydration of a self-aldol condensation
product?
A) 4-methyl-3-penten-2-one
B) 4-methyl-4-penten-2-one
C) 4-methyl-5-hexen-2-one
D) 4-methyl-4-heken-2-one
E) 3-methyl-4-penten-

Organic Chemistry

Aldehydes & Ketones Solutions

Mechs for q 4 Mech writer name 4. Which of the following could result from the dehydration of a self-aldol condensation product? A) 4-methyl-3-penten-2-one B) 4-methyl-4-penten-2-one C) 4-methyl-5-hexen-2-one D) 4-methyl-4-heken-2-one E) 3-methyl-4-penten-2-one

6. Synthesize the following compounds from the given starting material. You can add on
do any alkyl/ alkyl halide under 8 carbons or any necessary inorganic reagent needed (this
includes triphenyl phosphine (Ph3P). Please draw all intermediates and reagent

Organic Chemistry

Aldehydes & Ketones Solutions

6. Synthesize the following compounds from the given starting material. You can add on do any alkyl/ alkyl halide under 8 carbons or any necessary inorganic reagent needed (this includes triphenyl phosphine (Ph3P). Please draw all intermediates and reagents necessary to get to the product. (10 pts ea.) a.

RO
stjohns.instructure.com
Question 3
2 pts
An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of
reaction is this?
a Fischer esterification
a Hell-Volhard-Zelinsky reaction
a base-mediated aldol condensation
an

Organic Chemistry

Aldehydes & Ketones Solutions

RO stjohns.instructure.com Question 3 2 pts An enolate attacks an aldehyde and the resulting product is subsequently protonated. What type of reaction is this? a Fischer esterification a Hell-Volhard-Zelinsky reaction a base-mediated aldol condensation an acid-catalyzed aldol condensation Question 4 2 pts Which of the following could result from the dehydration of a self-aldol condensation product? 4-methyl-3-penten-2-one 4-methyl-4-penten-2-one 4-methyl-4-hexen-2-one Unified) 4-methyl-5-hexen-2-one 3-methyl-4-penten-2-one wer Question 5 2 pts 20 : 3 & 7 5 6 8 > o 9 W E R T Y C 1 O P > S D F G H J K < X C V B N > M 42 command option

Which of the following is the product of the reaction sequence shown below?
heat
(1) NaOEt
(2) H30*
(1) NaOH, H2O, heat
(2) H307
2
OEt
cements
nents
2-propylbutanoic acid
sions
2-ethylpentanoic acid
es
4-heptanone
ble
4-methyl-3-hexanone
es
es
Quizzes
2 pt

Organic Chemistry

Aldehydes & Ketones Solutions

Which of the following is the product of the reaction sequence shown below? heat (1) NaOEt (2) H30* (1) NaOH, H2O, heat (2) H307 2 OEt cements nents 2-propylbutanoic acid sions 2-ethylpentanoic acid es 4-heptanone ble 4-methyl-3-hexanone es es Quizzes 2 pts Question 3 Collaborations Folio What is the aldol addition product of propanal? Piazza Badges O CH3CH2CH NaOH, HÀO oºc Cisco Webex NameCoach (Unified) 2-hydroxy-2-methylpentanal Folio Follett Discover 4-hydroxyhexanal 3-hydroxyhexanal 3-hydroxy-2-methylpentanal

21 Problems
Question 28 of 30
>
OH
1) NaH 25°C
2) Mel
OH 3) H20+
Ph
4) PCC, H20
1)Ph2Culi
2) H30*
OH 3) LiAlH4
4) PCC, CH2Cl2
Ph
1) PCC, CH2Cl2
2) Ph2Culi
OH 3) Mel
Ph
4) MeNH2
[H], (H2O)
MacBook Pro
<
Q

Organic Chemistry

Aldehydes & Ketones Solutions

21 Problems Question 28 of 30 > OH 1) NaH 25°C 2) Mel OH 3) H20+ Ph 4) PCC, H20 1)Ph2Culi 2) H30* OH 3) LiAlH4 4) PCC, CH2Cl2 Ph 1) PCC, CH2Cl2 2) Ph2Culi OH 3) Mel Ph 4) MeNH2 [H], (H2O) MacBook Pro < Q

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