Reductions Involving Aldehydes or Ketones

Q. Acetophenone on reduction with Zn/Hg in the presence of HCl gives

1. Toluene
2. Benzene
3. Ethyl benzene
4. Xylene

Q. A compound $‘A^{\prime }$ with the empirical formula $C_3{H}_6{O}_2$ has a fruity smell. It reacts with $\text{DIBAL}-H/H_{2}O$ at ultra low temperatures. After work-up, we get $‘X^{\prime }$ and $‘Y^{\prime }$. $‘X^{\prime }$ on treating with dilute $NaOH$ forms $‘Z^{\prime }$. ${}^{\prime }{Z}^{\prime }$ doesn’t have a hydroxyl group and it reacts with ${\left(C{H}_3\right)}_{2}CuLi$ to give $M$. $‘Z^{\prime }$ also reacts with $C{H}_{3}MgBr$ to give $‘N^{\prime }$. Based on this passage, answer the following questions:
Which of the following is/are true?

1. $‘M^{\prime }$ has a carbon-carbon double bond
2. $‘M^{\prime }$ is a carbonyl compound
3. $‘N^{\prime }$ has a carbon carbon double bond
4. $‘N^{\prime }$ is an alochol

Q.

Ethyl alcohol has more elements than water.

1. True
2. False

Q.

Reduction of aldehydes or ketones into hydrocarbons using hydrazine and sodium ethoxide is called:

1. Clemmensen reduction

2. Cope reduction

3. Dow reduction

4. Wolff-Kishner reduction

Q.

There are two scenarios and in either case, we start with 5-oxohexanal. A reagent or sequence of reactions "A"
helps convert the substrate into 6-hydroxyhexan-2-one. On the other hand, a reagent or sequence of reactions "B"
converts the starting compound into 5-hydroxyhexanal. A and B are:

1. A: 1 eq. $NaB{H}_4$ followed by $H_3{O}^{+}$;
   B: 1 eq. $HOC{H}_{2}C{H}_{2}OH$, followed by $NaB{H}_4$ plus $H_3{O}^{+}$

2. A: 1 eq. $H_2$ Pt in low pressure;
   B: 1 eq. $HOC{H}_{2}C{H}_{2}OH$, followed by $NaB{H}_4$ plus $H_3{O}^{+}$

3. A: 1 eq. $HOC{H}_{2}C{H}_{2}OH$, followed by $NaB{H}_4$ plus $H_3{O}^{+}$;
   B: 1 eq. $NaB{H}_4$ followed by $H_3{O}^{+}$

4. None of the above

Q. Answer the following by appropriately matching the lists based on the information given in the paragraph.

List-I includes starting materials and reagents of selected chemical reactions. List-II gives structures of compounds that may be formed as intermediate products and/or final products from the reactions of List-I.

Which of the following options has the correct combination considering List-I and List-II?

1. (II), (P), (S), (T)
2. (II), (P), (S), (U)
3. (I), (S), (Q), (R)
4. (I), (Q), (T), (U)

Q. Predict major organic product from the following reaction.

1. 
2. 
3. 
4. 

Q.
The above reaction and reagent are respectively -

1. $Cannizaroreaction,NaOH$
2. $Aldolcondesnation,O{H}^{⊝}$
3. $Tischenkoreaction,Al(O{C}_2{H}_5{)}_3$
4. $Perkinreaction(C{H}_{3}CO{)}_{2}O$

Q. The enol from of acetone after treatment with $D_{2}O$ gives:

1. $C{H}_3-\stackrel{\stackrel{OD}{|}}{C}=C{H}_2$
2. $C{D}_3-\stackrel{\stackrel{O}{||}}{C}-C{D}_3$
3. $C{H}_2=\stackrel{\stackrel{OH}{|}}{C}-C{H}_{2}D$
4. $C{D}_3=\stackrel{\stackrel{OD}{|}}{C}-C{D}_3$

Q. Acetophenone is reduced by $LiAl{H}_4$ to

1. Toluene
2. Ethyl benzene
3. 1-Phenylethanol
4. Phenol

Q.

The correct structure of product A from the following reaction is:

1. 

2. 

3. 

4. 

Q. Reduction of aldehydes and ketones into hydrocarbons using zinc amalgam and concentrated hydrochloric acid is called

1. Cope reduction
2. Dow reduction
3. Wolff Kishner reduction
4. Clemmensen reduction

Q. Reduction of $C{H}_{3}C{H}_{2}COC{H}_3$ to $C{H}_{3}C{H}_{2}C{H}_{2}C{H}_3$ can be carried out with:

1. $H_2/Pd$
2. $Zn-Hg/HCl$
3. $NaB{H}_4$
4. $LiAl{H}_4$

Q. The enol from of acetone after treatment with $D_{2}O$ gives:

1. $C{H}_3-\stackrel{\stackrel{OD}{|}}{C}=C{H}_2$
2. $C{D}_3-\stackrel{\stackrel{O}{||}}{C}-C{D}_3$
3. $C{H}_2=\stackrel{\stackrel{OH}{|}}{C}-C{H}_{2}D$
4. $C{D}_3=\stackrel{\stackrel{OD}{|}}{C}-C{D}_3$

Q.

We start with 2-cyclohexenone and subject it to (separate) reagents/reaction sequences A, B, C and D.
Each of these correspondingly yields the products.

From the options given, choose the correct ones that could be the reaction sequences

1. 

2. 

3. 

4. 

Q.

Acetaldehyde cannot give:

1. Iodoform test
2. Lucas test
3. Benedict test

4. Tollens test

Q. A compound $‘A^{\prime }$ with the empirical formula $C_3{H}_6{O}_2$ has a fruity smell. It reacts with $\text{DIBAL}-H/H_{2}O$ at ultra low temperatures. After work-up, we get $‘X^{\prime }$ and $‘Y^{\prime }$. $‘X^{\prime }$ on treating with dilute $NaOH$ forms $‘Z^{\prime }$. ${}^{\prime }{Z}^{\prime }$ doesn’t have a hydroxyl group and it reacts with ${\left(C{H}_3\right)}_{2}CuLi$ to give $M$. $‘Z^{\prime }$ also reacts with $C{H}_{3}MgBr$ to give $‘N^{\prime }$. Based on this passage, answer the following questions:
Which of the following is/are true?

1. $‘M^{\prime }$ has a carbon-carbon double bond
2. $‘M^{\prime }$ is a carbonyl compound
3. $‘N^{\prime }$ has a carbon carbon double bond
4. $‘N^{\prime }$ is an alochol

Q. The enol form of acetone, after treatment with $D_2,O,$ gives

1. $C{H}_3-\stackrel{\stackrel{OD}{|}}{C}=C{H}_2$
2. $C{D}_3-\stackrel{\stackrel{O}{||}}{C}=C{D}_3$
3. $C{H}_2=\stackrel{\stackrel{OH}{|}}{C}=C{H}_{2}D$
4. $C{D}_2=\stackrel{\stackrel{OD}{|}}{C}=C{D}_2$

Q.

Assertion : Formaldehyde cannot be prepared by Rosenmund's reduction.

Reason : Acid chlorides can be reduced into aldehydes with hydrogen in boiling xylene using palladium or platinum as a catalyst supported on barium sulphate. This is known as Rosenmund's reduction.

1. If both assertion and reason are true and the reason is the correct explanation of the assertion.

2. If both assertion and reason are true but reason is not the correct explanation of the assertion.

3. If assertion is true but reason is false.

4. If the assertion and reason both are false.

5. If assertion is false but reason is true.